[ CAS No. 870987-64-7 ] {[proInfo.proName]}

Name: 870987-64-7|Di-μ-chlorotetrakis[3,5-difluoro-2-[5-trifluoromethyl-2-pyridinyl-kN)phenyl-kC]diiridium(III)|98%
Brand: Ambeed
SKU: A1175857
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Quality Control of [ 870987-64-7 ]

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Product Details of [ 870987-64-7 ]

CAS No. :	870987-64-7	MDL No. :	MFCD29037184
Formula :	C₄₈H₂₀Cl₂F₂₀Ir₂N₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	1488.01	Pubchem ID :	-
Synonyms :

Safety of [ 870987-64-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P264-P280-P337+P313-P305+P351+P338-P302+P352-P332+P313-P362	UN#:	N/A
Hazard Statements:	H315-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 870987-64-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 870987-64-7 ]
Downstream synthetic route of [ 870987-64-7 ]

[ 870987-64-7 ] Synthesis Path-Upstream 1~3

1
[ 870987-64-7 ]
[ 72914-19-3 ]
[ 676525-77-2 ]

Reference： [1] Chemistry - A European Journal, 2018, vol. 24, # 44, p. 11314 - 11318

2
[ 870987-64-7 ]
[ 72914-19-3 ]
[ 870987-63-6 ]

Yield	Reaction Conditions	Operation in experiment
75%	Stage #1: for 15 h; Reflux; Inert atmosphere	Bis-(μ)-chlorotetrakis(2-(4,6-difluoromethylphenyl)-pyridinato-C²,N)diiridium(III) (0.09 mmol, 0.13 g) was heated to reflux with 4,4’-di-tert-butyl-2,2’-dipyridyl (0.20 mmol, 0.054g) in ethylene glycol (6.0 mL) under nitrogen with constant stirring for 15h. Upon cooling to room temperature, the mixture was transferred to a separatory funnel with water (60 mL) and washed with hexanes (3×30 mL). The aqueous layer was heated to 85 °C for 5 min to remove residual hexanes. A 10 mL aqueous ammonium hexafluorophosphate solution (1.0g in 10 mL deionized water) was added to the reaction mixture, producing a yellow-green amorphous powder. This precipitate was filtered, dried, and recrystallized by acetone:pentane vapor diffusion, giving the pure product, [Ir(dF(CF₃)ppy)₂(dtbbpy)]-(PF₆). Yield: 0.15 g (75percent).
121 mg	Stage #1: at 150℃; for 15 h; Inert atmosphere	General procedure: Heteroleptic iridium 4xy were synthesized in a two-step procedure[42,43]. In the first step, chloro-bridged dimer was synthesized by charging a two-necked reaction flask with magnetic stir bar, iridium(III) chloride (1 equiv), ligand (2.26 equiv), and a 2:1 v:v mixture of 2-methoxyethanol/water. The mixture was degased with Ar (via Ar bubbling) and heated under reflux at 120 °C with constant stirring overnight. The reaction mixture cooled to room temperature and filtered. The precipitate was washed with water (3x10 mL), dried in air and taken onto the second step without further purification unless noted. In the second step, the chloro bridging dimer (1 equiv), bipyridyl ligand (2.2 equiv) and ethylene glycol were placed in a two-necked flask and then flushed with Ar. The mixture was heated at 150 °C for 15 h and then cooled. The cooled reaction mixture was washed hexane (3 10 mL) and mixture was heated to 85 °C for 5 min to remove residual hexane. Aqueous ammonium hexafluorophosphate (sat. solution) was added to the reaction mixture causing the iridium-PF₆ salt to precipitate,which was filtered, dried and recrystallized (acetone/ether).

Reference： [1] Journal of Organic Chemistry, 2015, vol. 80, # 15, p. 7642 - 7651
[2] Tetrahedron Letters, 2018, vol. 59, # 21, p. 2046 - 2049
[3] Journal of Organometallic Chemistry, 2015, vol. 776, p. 51 - 59

3
[ 17084-13-8 ]
[ 870987-64-7 ]
[ 72914-19-3 ]
[ 870987-63-6 ]

Reference： [1] Organic Letters, 2018,

[ 870987-64-7 ] Synthesis Path-Downstream 1~57

1
iridium(III) chloride hydrate [ No CAS ]
[ 387827-64-7 ]
[ 870987-64-7 ]

Reference： [1]Inorganic Chemistry,2008,vol. 47,p. 2039 - 2048

2
[ 870987-64-7 ]
[ 123-54-6 ]
[Ir(acetylacetonato)(2-(2,4-difluorophenyl)-5-trifluoromethylpyridine(-H)-κN,C)2] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (CH₃CH₂CH₂CH₂)4NOH In ethanol; dichloromethane 2.7 equiv. of acetylacetone added to soln. of 1 equiv. of Ir complex in CH2Cl2, 40% soln. of 16.9 equiv. of Bu4NOH in H2O added, mixt. refluxed for 18 h; according to Nazeeruddin M.K. et al., J. Chem. Soc. 2003, 125,8790; cooling, filtration through silica, eluted with CH2Cl2, yellow soln. concd., EtOH added, concn., suspn. cooled at 0°C for 10 min, solid filtered off, washed with cold EtOH, dried under vac.; elem. anal.;

Reference： [1]Coughlin, Frederick J.; Westrol, Michael S.; Oyler, Karl D.; Byrne, Neal; Kraml, Christina; Zysman-Colman, Eli; Lowry, Michael S.; Bernhard, Stefan [Inorganic Chemistry, 2008, vol. 47, # 6, p. 2039 - 2048]

3
[ 17084-13-8 ]
[ 366-18-7 ]
[ CAS Unavailable ]
[ 870987-64-7 ]
[ 1092775-62-6 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol soln. of Ir complex (1 equiv.) and org. ligand (2.1 equiv.) refluxed overnight; cooled to room temp.; filtered; satd. aq. NH4PF6 added; ppt. filtered; washed with H2O, EtOH and Et2O; column chromy. on silica gel (MeCN/H2O satd. aq. KNO3 100:10:1 as sluent); evapd. (vac.); satd. aq. KPF6 added; elem. anal.;

Reference： [1]Hanss, David; Freys, Jonathan C.; Bernardinelli, Gerald; Wenger, Oliver S. [European Journal of Inorganic Chemistry, 2009, # 32, p. 4850 - 4859]

4
iridium(III) chloride trihydrate [ No CAS ]
[ 387827-64-7 ]
[ 870987-64-7 ]

Reference： [1]European Journal of Inorganic Chemistry,2009,p. 4850 - 4859

5
ammonium hexafluorophosphate [ No CAS ]
[ 870987-64-7 ]
[ 1762-42-1 ]
C₄₀H₂₆F₁₀IrN₄O₄⁽¹⁺⁾*F₆P^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52.7%	Stage #1: bis-(μ)-chlorotetrakis[2-(2’,4’-difluorophenyl)-5-trifluoromethylpyridinato]-(C2,N)diiridium(III); 4,4'-bis(ethoxycarbonyl)-2,2'-bipyridine In ethanol for 68h; Reflux; Stage #2: ammonium hexafluorophosphate In water; acetone

Reference： [1]Chirdon, Danielle N.; McCusker, Catherine E.; Castellano, Felix N.; Bernhard, Stefan [Inorganic Chemistry, 2013, vol. 52, # 15, p. 8795 - 8804]

6
[ 870987-64-7 ]
[ 29420-49-3 ]
[ 72914-19-3 ]
C₄₂H₃₄F₁₀IrN₄⁽¹⁺⁾*C₄F₉O₃S^(1-) [ No CAS ]

Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 6120 - 6125

7
[ 387827-64-7 ]
iridium(III) chloride n-hydrate [ No CAS ]
[ 870987-64-7 ]

Yield	Reaction Conditions	Operation in experiment
61%	In 2-ethoxy-ethanol; water; at 120℃; for 14h;	89.0 mg (0.300 mmol, 1.0 eq) iridium(III) chloride hydrate and 179 mg (0.690 mmol, 2.3 eq) 2-phenylpyridine are suspended in 4 mL 2-ethoxyethanol and 2 mL water and the mixture is stirred at120 C for 14 hours. After cooling down, the precipitate is filtered off, washed with 20 mL water (3x)and then dissolved in dichloromethane. The organic phase is dried over Na2SO4, the solvent is removed in vacuo and the residue is carefully washed with diethyl ether to obtain 136 mg (61%) bis-(mu)-chlorotetrakis[2-(2?,4?-difluorophenyl)-5-trifluoromethylpyridinato]-(C2,N)diiridium(III) as yellow solid.
	In 2-methoxy-ethanol; water; at 120℃;Inert atmosphere;	General procedure: Heteroleptic iridium 4xy were synthesized in a two-step procedure[42,43]. In the first step, chloro-bridged dimer was synthesized by charging a two-necked reaction flask with magnetic stir bar, iridium(III) chloride (1 equiv), ligand (2.26 equiv), and a 2:1 v:v mixture of 2-methoxyethanol/water. The mixture was degased with Ar (via Ar bubbling) and heated under reflux at 120 C with constant stirring overnight. The reaction mixture cooled to room temperature and filtered. The precipitate was washed with water (3x10 mL), dried in air and taken onto the second step without further purification unless noted. In the second step, the chloro bridging dimer (1 equiv), bipyridyl ligand (2.2 equiv) and ethylene glycol were placed in a two-necked flask and then flushed with Ar. The mixture was heated at 150 C for 15 h and then cooled. The cooled reaction mixture was washed hexane (3 10 mL) and mixture was heated to 85 C for 5 min to remove residual hexane. Aqueous ammonium hexafluorophosphate (sat. solution) was added to the reaction mixture causing the iridium-PF6 salt to precipitate,which was filtered, dried and recrystallized (acetone/ether).

Reference： [1]Organic Letters,2018,vol. 20,p. 6794 - 6798
[2]Journal of the American Chemical Society,2015,vol. 137,p. 2195 - 2198
[3]Synlett,2016,vol. 27,p. 1056 - 1060
[4]Inorganic Chemistry,2019,vol. 58,p. 855 - 860
[5]Journal of Organometallic Chemistry,2015,vol. 776,p. 51 - 59

8
[ 66-71-7 ]
ammonium hexafluorophosphate [ No CAS ]
[ 870987-64-7 ]
Ir[2-(2,4-difluorophenyl)-5-trifluoromethylpyridine]₂(1,10-phenantroline)PF₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	Stage #1: 1,10-Phenanthroline; bis-(μ)-chlorotetrakis[2-(2’,4’-difluorophenyl)-5-trifluoromethylpyridinato]-(C2,N)diiridium(III) In ethylene glycol at 150℃; Inert atmosphere; Schlenk technique; Stage #2: ammonium hexafluorophosphate In water; ethylene glycol Inert atmosphere; Schlenk technique;
64 mg	Stage #1: 1,10-Phenanthroline; bis-(μ)-chlorotetrakis[2-(2’,4’-difluorophenyl)-5-trifluoromethylpyridinato]-(C2,N)diiridium(III) In ethylene glycol at 150℃; for 15h; Inert atmosphere; Stage #2: ammonium hexafluorophosphate In water	General Procedure C for the synthesis of cationic heteroleptic [Ir (C^N)₂(bpy)]⁺PF6^-complexes (4xy). General procedure: Heteroleptic iridium 4xy were synthesized in a two-step procedure[42,43]. In the first step, chloro-bridged dimer was synthesized by charging a two-necked reaction flask with magnetic stir bar, iridium(III) chloride (1 equiv), ligand (2.26 equiv), and a 2:1 v:v mixture of 2-methoxyethanol/water. The mixture was degased with Ar (via Ar bubbling) and heated under reflux at 120 °C with constant stirring overnight. The reaction mixture cooled to room temperature and filtered. The precipitate was washed with water (3x10 mL), dried in air and taken onto the second step without further purification unless noted. In the second step, the chloro bridging dimer (1 equiv), bipyridyl ligand (2.2 equiv) and ethylene glycol were placed in a two-necked flask and then flushed with Ar. The mixture was heated at 150 °C for 15 h and then cooled. The cooled reaction mixture was washed hexane (3 10 mL) and mixture was heated to 85 °C for 5 min to remove residual hexane. Aqueous ammonium hexafluorophosphate (sat. solution) was added to the reaction mixture causing the iridium-PF6 salt to precipitate,which was filtered, dried and recrystallized (acetone/ether).

Reference： [1]Peng, Long; Li, Zheqi; Yin, Guoyin [Organic Letters, 2018, vol. 20, # 7, p. 1880 - 1883]
[2]Singh, Anuradha; Teegardin, Kip; Kelly, Megan; Prasad, Kariate S.; Krishnan, Sadagopan; Weaver, Jimmie D. [Journal of Organometallic Chemistry, 2015, vol. 776, p. 51 - 59]

9
[ 366-18-7 ]
ammonium hexafluorophosphate [ No CAS ]
[ 870987-64-7 ]
bis[3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridyl]phenyl]iridium⁽¹⁺⁾; 2-(2-pyridyl)pyridine; hexafluorophosphate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	Stage #1: [2,2]bipyridinyl; bis-(μ)-chlorotetrakis[2-(2’,4’-difluorophenyl)-5-trifluoromethylpyridinato]-(C2,N)diiridium(III) In ethylene glycol at 150℃; for 18h; Inert atmosphere; Stage #2: ammonium hexafluorophosphate In water for 0.333333h; Cooling with ice;
88%	Stage #1: [2,2]bipyridinyl; bis-(μ)-chlorotetrakis[2-(2’,4’-difluorophenyl)-5-trifluoromethylpyridinato]-(C2,N)diiridium(III) In ethylene glycol at 150℃; for 24h; Inert atmosphere; Stage #2: ammonium hexafluorophosphate In water at 20℃; Inert atmosphere;
58%	Stage #1: [2,2]bipyridinyl; bis-(μ)-chlorotetrakis[2-(2’,4’-difluorophenyl)-5-trifluoromethylpyridinato]-(C2,N)diiridium(III) In ethylene glycol at 150℃; for 24h; Inert atmosphere; Stage #2: ammonium hexafluorophosphate In water

105 mg

Stage #1: [2,2]bipyridinyl; bis-(μ)-chlorotetrakis[2-(2’,4’-difluorophenyl)-5-trifluoromethylpyridinato]-(C2,N)diiridium(III) In ethylene glycol at 150℃; for 15h; Inert atmosphere; Stage #2: ammonium hexafluorophosphate In water

General Procedure C for the synthesis of cationic heteroleptic [Ir (C^N)₂(bpy)]⁺PF6^-complexes (4xy). General procedure: Heteroleptic iridium 4xy were synthesized in a two-step procedure[42,43]. In the first step, chloro-bridged dimer was synthesized by charging a two-necked reaction flask with magnetic stir bar, iridium(III) chloride (1 equiv), ligand (2.26 equiv), and a 2:1 v:v mixture of 2-methoxyethanol/water. The mixture was degased with Ar (via Ar bubbling) and heated under reflux at 120 °C with constant stirring overnight. The reaction mixture cooled to room temperature and filtered. The precipitate was washed with water (3x10 mL), dried in air and taken onto the second step without further purification unless noted. In the second step, the chloro bridging dimer (1 equiv), bipyridyl ligand (2.2 equiv) and ethylene glycol were placed in a two-necked flask and then flushed with Ar. The mixture was heated at 150 °C for 15 h and then cooled. The cooled reaction mixture was washed hexane (3 10 mL) and mixture was heated to 85 °C for 5 min to remove residual hexane. Aqueous ammonium hexafluorophosphate (sat. solution) was added to the reaction mixture causing the iridium-PF6 salt to precipitate,which was filtered, dried and recrystallized (acetone/ether).

Reference： [1]Oderinde, Martins S.; Varela-Alvarez, Adrian; Aquila, Brian; Robbins, Daniel W.; Johannes, Jeffrey W. [Journal of Organic Chemistry, 2015, vol. 80, # 15, p. 7642 - 7651]
[2]Primer, David N.; Karakaya, Idris; Tellis, John C.; Molander, Gary A. [Journal of the American Chemical Society, 2015, vol. 137, # 6, p. 2195 - 2198]
[3]Sayre, Hannah; Ripberger, Hunter H.; Odella, Emmanuel; Zieleniewska, Anna; Heredia, Daniel A.; Rumbles, Garry; Scholes, Gregory D.; Moore, Thomas A.; Moore, Ana L.; Knowles, Robert R. [Journal of the American Chemical Society, 2021, vol. 143, # 33, p. 13034 - 13043]
[4]Singh, Anuradha; Teegardin, Kip; Kelly, Megan; Prasad, Kariate S.; Krishnan, Sadagopan; Weaver, Jimmie D. [Journal of Organometallic Chemistry, 2015, vol. 776, p. 51 - 59]

10
ammonium hexafluorophosphate [ No CAS ]
[ 870987-64-7 ]
[ 72914-19-3 ]
[ 870987-63-6 ]

Yield	Reaction Conditions	Operation in experiment
75%		Bis-(mu)-chlorotetrakis(2-(4,6-difluoromethylphenyl)-pyridinato-C2,N)diiridium(III) (0.09 mmol, 0.13 g) was heated to reflux with 4,4?-di-tert-butyl-2,2?-dipyridyl (0.20 mmol, 0.054g) in ethylene glycol (6.0 mL) under nitrogen with constant stirring for 15h. Upon cooling to room temperature, the mixture was transferred to a separatory funnel with water (60 mL) and washed with hexanes (3×30 mL). The aqueous layer was heated to 85 C for 5 min to remove residual hexanes. A 10 mL aqueous ammonium hexafluorophosphate solution (1.0g in 10 mL deionized water) was added to the reaction mixture, producing a yellow-green amorphous powder. This precipitate was filtered, dried, and recrystallized by acetone:pentane vapor diffusion, giving the pure product, [Ir(dF(CF3)ppy)2(<strong>[72914-19-3]dtbbpy</strong>)]-(PF6). Yield: 0.15 g (75%).
121 mg		General procedure: Heteroleptic iridium 4xy were synthesized in a two-step procedure[42,43]. In the first step, chloro-bridged dimer was synthesized by charging a two-necked reaction flask with magnetic stir bar, iridium(III) chloride (1 equiv), ligand (2.26 equiv), and a 2:1 v:v mixture of 2-methoxyethanol/water. The mixture was degased with Ar (via Ar bubbling) and heated under reflux at 120 C with constant stirring overnight. The reaction mixture cooled to room temperature and filtered. The precipitate was washed with water (3x10 mL), dried in air and taken onto the second step without further purification unless noted. In the second step, the chloro bridging dimer (1 equiv), bipyridyl ligand (2.2 equiv) and ethylene glycol were placed in a two-necked flask and then flushed with Ar. The mixture was heated at 150 C for 15 h and then cooled. The cooled reaction mixture was washed hexane (3 10 mL) and mixture was heated to 85 C for 5 min to remove residual hexane. Aqueous ammonium hexafluorophosphate (sat. solution) was added to the reaction mixture causing the iridium-PF6 salt to precipitate,which was filtered, dried and recrystallized (acetone/ether).

Reference： [1]Journal of Organic Chemistry,2015,vol. 80,p. 7642 - 7651
[2]Tetrahedron Letters,2018,vol. 59,p. 2046 - 2049
[3]Journal of Organometallic Chemistry,2015,vol. 776,p. 51 - 59

11
ammonium hexafluorophosphate [ No CAS ]
[ 870987-64-7 ]
5-(3’’,3’’-dimethyl-1’’-yn-1’’-yl)-2,2’-bipyridine [ No CAS ]
bis[2’’-(2’’’,4’’’-difluorophenyl)-5’’-trifluoromethylpyridine][5-(III,III-dimethyl-but-I-yn-Iyl)-2,2’-bipyridine]iridium(III)hexafluorophosphate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	Stage #1: bis-(μ)-chlorotetrakis[2-(2’,4’-difluorophenyl)-5-trifluoromethylpyridinato]-(C2,N)diiridium(III); 5-(3’’,3’’-dimethyl-1’’-yn-1’’-yl)-2,2’-bipyridine In ethylene glycol at 150℃; Stage #2: ammonium hexafluorophosphate In dichloromethane; ethylene glycol Further stages;	General procedure for the synthesis of iridium(III) complexes: General procedure: Bis-(μ)-chlorotetrakis[2-(2’,4’-difluorophenyl)-5-trifluoromethylpyridinato]-(C2,N)diiridium(III)(0.5 eq) and bipyridine ligand (1.1 eq) are suspended in ethylene glycol (15mM) and the mixture isstirred at 150 °C. After cooling down, equal amounts of aqueous NH4PF6 solution (20 mM) anddichloromethane are added and the aqueous phase is extracted with dichloromethane (3x). The organicphase is dried over Na2SO4, the solvent is removed in vacuo and the crude product is purified by columnchromatography.

Reference： [1]Böhm, Alexander; Bach, Thorsten [Synlett, 2016, vol. 27, # 7, p. 1056 - 1060]

12
ammonium hexafluorophosphate [ No CAS ]
[ 870987-64-7 ]
5-(3’’,3’’-dimethylbutyl)-2,2’-bipyridine [ No CAS ]
bis[2’’-(2’’’,4’’’-difluorophenyl)-5’’-trifluoromethylpyridine][5-(III,III-dimethyl-but-I-yl)-2,2’-bipyridine]iridium(III)hexafluorophosphate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	Stage #1: bis-(μ)-chlorotetrakis[2-(2’,4’-difluorophenyl)-5-trifluoromethylpyridinato]-(C2,N)diiridium(III); 5-(3’’,3’’-dimethylbutyl)-2,2’-bipyridine In ethylene glycol at 150℃; Stage #2: ammonium hexafluorophosphate In dichloromethane; ethylene glycol Further stages;	General procedure for the synthesis of iridium(III) complexes: General procedure: Bis-(μ)-chlorotetrakis[2-(2’,4’-difluorophenyl)-5-trifluoromethylpyridinato]-(C2,N)diiridium(III)(0.5 eq) and bipyridine ligand (1.1 eq) are suspended in ethylene glycol (15mM) and the mixture isstirred at 150 °C. After cooling down, equal amounts of aqueous NH4PF6 solution (20 mM) anddichloromethane are added and the aqueous phase is extracted with dichloromethane (3x). The organicphase is dried over Na2SO4, the solvent is removed in vacuo and the crude product is purified by columnchromatography.

Reference： [1]Böhm, Alexander; Bach, Thorsten [Synlett, 2016, vol. 27, # 7, p. 1056 - 1060]

13
ammonium hexafluorophosphate [ No CAS ]
[ 870987-64-7 ]
(3aS, 4R, 7S, 7aR, 8R)-8-(2’’,2’’’-bipyridine-5’’-yl)octahydro-1H-4,7-methanoisoindol-1-one [ No CAS ]
bis[2’’-(2’’’,4’’’-difluorophenyl)-5’’-trifluoromethylpyridine][5-((IIIaS,IVR,VIIS,VIIaR,VIIIR)-VIII-ethynyloctahydro-1H-IV,VII-methanoisoindol-I-one-II’’-yl)-2,2’-bipyridine]iridium(III)-hexafluorophosphate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	Stage #1: bis-(μ)-chlorotetrakis[2-(2’,4’-difluorophenyl)-5-trifluoromethylpyridinato]-(C2,N)diiridium(III); (3aS, 4R, 7S, 7aR, 8R)-8-(2’’,2’’’-bipyridine-5’’-yl)octahydro-1H-4,7-methanoisoindol-1-one In ethylene glycol at 150℃; Stage #2: ammonium hexafluorophosphate In dichloromethane; ethylene glycol Further stages;	General procedure for the synthesis of iridium(III) complexes: General procedure: Bis-(μ)-chlorotetrakis[2-(2’,4’-difluorophenyl)-5-trifluoromethylpyridinato]-(C2,N)diiridium(III)(0.5 eq) and bipyridine ligand (1.1 eq) are suspended in ethylene glycol (15mM) and the mixture isstirred at 150 °C. After cooling down, equal amounts of aqueous NH4PF6 solution (20 mM) anddichloromethane are added and the aqueous phase is extracted with dichloromethane (3x). The organicphase is dried over Na2SO4, the solvent is removed in vacuo and the crude product is purified by columnchromatography.

Reference： [1]Böhm, Alexander; Bach, Thorsten [Synlett, 2016, vol. 27, # 7, p. 1056 - 1060]

14
ammonium hexafluorophosphate [ No CAS ]
[ 870987-64-7 ]
(3aS, 4R, 7S, 7aR, 8R)-8-[2’-(2’’,2’’’-bipyridine-5’’-yl)ethyl]octahydro-1H-4,7-methanoisoindol-1-one [ No CAS ]
bis[2’’-(2’’’,4’’’-difluorophenyl)-5’’-trifluoromethylpyridine][5-((IIIaS,IVR,VIIS,VIIaR,VIIIR)-VIII-ethyloctahydro-1H-IV,VII-methanoisoindol-I-one-II’’-yl)-2,2’-bipyridine]iridium(III)-hexafluorophosphate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	Stage #1: bis-(μ)-chlorotetrakis[2-(2’,4’-difluorophenyl)-5-trifluoromethylpyridinato]-(C2,N)diiridium(III); (3aS, 4R, 7S, 7aR, 8R)-8-[2’-(2’’,2’’’-bipyridine-5’’-yl)ethyl]octahydro-1H-4,7-methanoisoindol-1-one In ethylene glycol at 150℃; Stage #2: ammonium hexafluorophosphate In dichloromethane; ethylene glycol Further stages;	General procedure for the synthesis of iridium(III) complexes: General procedure: Bis-(μ)-chlorotetrakis[2-(2’,4’-difluorophenyl)-5-trifluoromethylpyridinato]-(C2,N)diiridium(III)(0.5 eq) and bipyridine ligand (1.1 eq) are suspended in ethylene glycol (15mM) and the mixture isstirred at 150 °C. After cooling down, equal amounts of aqueous NH4PF6 solution (20 mM) anddichloromethane are added and the aqueous phase is extracted with dichloromethane (3x). The organicphase is dried over Na2SO4, the solvent is removed in vacuo and the crude product is purified by columnchromatography.

Reference： [1]Böhm, Alexander; Bach, Thorsten [Synlett, 2016, vol. 27, # 7, p. 1056 - 1060]

15
ammonium hexafluorophosphate [ No CAS ]
[ 387827-64-7 ]
[ 870987-64-7 ]
bis[2’’-(2’’’,4’’’-difluorophenyl)-5’’-trifluoromethylpyridine](2,2’-bipyridine)iridium(III) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%		General procedure: Bis-(mu)-chlorotetrakis[2-(2?,4?-difluorophenyl)-5-trifluoromethylpyridinato]-(C2,N)diiridium(III)(0.5 eq) and bipyridine ligand (1.1 eq) are suspended in ethylene glycol (15mM) and the mixture isstirred at 150 C. After cooling down, equal amounts of aqueous NH4PF6 solution (20 mM) anddichloromethane are added and the aqueous phase is extracted with dichloromethane (3x). The organicphase is dried over Na2SO4, the solvent is removed in vacuo and the crude product is purified by columnchromatography.

Reference： [1]Synlett,2016,vol. 27,p. 1056 - 1060

16
[ 144025-03-6 ]
[ 50488-42-1 ]
[ 870987-64-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: triphenylphosphine; palladium diacetate; potassium carbonate / water; ethanol; toluene / Inert atmosphere; Reflux 2: water; 2-ethoxy-ethanol / 120 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: potassium carbonate; palladium diacetate; triphenylphosphine / toluene; water; ethanol / Inert atmosphere; Reflux 2: water; 2-ethoxy-ethanol / 135 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: potassium carbonate; palladium diacetate; triphenylphosphine / ethanol; toluene; water / 16 h / Inert atmosphere; Reflux 2: water; 2-ethoxy-ethanol / 16 h / 150 °C / Inert atmosphere

	Multi-step reaction with 2 steps 1: palladium diacetate; triphenylphosphine; potassium carbonate / water; toluene; ethanol / 23 h / Inert atmosphere; Reflux 2: 2-ethoxy-ethanol; water / 23 h / 120 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: potassium carbonate; palladium diacetate; triphenylphosphine / toluene; water; ethanol / 16 h / Inert atmosphere; Reflux 2: water; 2-ethoxy-ethanol / 16 h / 150 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: potassium carbonate; palladium diacetate; triphenylphosphine / ethanol; toluene; water / 16 h / Inert atmosphere; Reflux 2: water; 2-ethoxy-ethanol / 16 h / 150 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: potassium carbonate; palladium diacetate; triphenylphosphine / toluene; ethanol; water / Reflux; Inert atmosphere 2: water; 2-methoxy-ethanol / 12 h / 120 °C / Inert atmosphere

Reference： [1]Zhu, Qilei; Gentry, Emily C.; Knowles, Robert R. [Angewandte Chemie - International Edition, 2016, vol. 55, # 34, p. 9969 - 9973][Angew. Chem., 2016, vol. 128, # 34, p. 10123 - 10127]
[2]Zhu, Qilei; Graff, David E.; Knowles, Robert R. [Journal of the American Chemical Society, 2018, vol. 140, # 2, p. 741 - 747]
[3]Rossolini, Thomas; Leitch, Jamie A.; Grainger, Rachel; Dixon, Darren J. [Organic Letters, 2018, vol. 20, # 21, p. 6794 - 6798]
[4]Neumann, Svenja; Wenger, Oliver S. [Inorganic Chemistry, 2019, vol. 58, # 1, p. 855 - 860]
[5]Rossolini, Thomas; Ferko, Branislav; Dixon, Darren J. [Organic Letters, 2019, vol. 21, # 17, p. 6668 - 6673]
[6]Dixon, Darren J.; Duarte, Fernanda; Leitch, Jamie A.; Rogova, Tatiana [Angewandte Chemie - International Edition, 2020, vol. 59, # 10, p. 4121 - 4130][Angew. Chem., 2020, vol. 132, # 10, p. 4150 - 4159,10]
[7]Mou, Ze-Dong; Wang, Jia-Xi; Zhang, Xia; Niu, Dawen [Advanced Synthesis and Catalysis, 2021, vol. 363, # 12, p. 3025 - 3029]

17
[ 387827-64-7 ]
iridium(III) chloride monohydrate [ No CAS ]
[ 870987-64-7 ]

Reference： [1]Organic Letters,2019,vol. 21,p. 6668 - 6673
[2]Journal of the American Chemical Society,2018,vol. 140,p. 741 - 747
[3]Chemistry - A European Journal,2018,vol. 24,p. 11314 - 11318
[4]Angewandte Chemie - International Edition,2016,vol. 55,p. 9969 - 9973
Angew. Chem.,2016,vol. 128,p. 10123 - 10127,5
[5]Journal of the American Chemical Society,2016,vol. 138,p. 12320 - 12323

18
[ 26042-63-7 ]
[ 870987-64-7 ]
[ 75-05-8 ]
8,8-diacetonitrile-11,11',13,13'-tetrafluoro-5,5'-bis(trifluoromethyl)-7λ,7'λ-diaza-8-irida-8,8'-spirobi[tricyclo[7.4.0.0,]tridecane]-1(9),1'(9'),2,2',4,4',6,6',10,10',12,12'-dodecaene-8,8,8-tris(ylium)-9,9'-diuide; hexafluoro-λ-phosphane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	In dichloromethane at 55℃; Inert atmosphere;
90%	In dichloromethane at 55℃; Inert atmosphere;
	In dichloromethane at 55℃; Inert atmosphere;

at 60℃;

General procedure: To a suspension of complex 11 (1050 mg, 0.70 mmol) in CH3CN (10 mL) was added AgPF6 (375 mg, 1.46mmol) in one portion. After stirring at 60 °C overnight, the mixture was cooled to room temperature and thesolid was filtered off. The filtrate was collected, evaporated to dryness and purified by columnchromatograph on silica gel to afford complex S1. To this complex (440 mg, 0.47 mmol) in CH3CN/H2O (5mL, 4:1), carboxylic acids containing pyridine ligand 2 (180 mg, 0.47 mmol, synthesized according to ourprevious report2) was added and then heated at 70 overnight. Afterwards, the volatile was removedunder vacuum and the residue was subjected to silica gel column chromatography to afford complex 3 as ayellow solid (570 mg, 90% yield over two steps).

Reference： [1]Zhu, Qilei; Graff, David E.; Knowles, Robert R. [Journal of the American Chemical Society, 2018, vol. 140, # 2, p. 741 - 747]
[2]Sayre, Hannah; Ripberger, Hunter H.; Odella, Emmanuel; Zieleniewska, Anna; Heredia, Daniel A.; Rumbles, Garry; Scholes, Gregory D.; Moore, Thomas A.; Moore, Ana L.; Knowles, Robert R. [Journal of the American Chemical Society, 2021, vol. 143, # 33, p. 13034 - 13043]
[3]Zhu, Qilei; Gentry, Emily C.; Knowles, Robert R. [Angewandte Chemie - International Edition, 2016, vol. 55, # 34, p. 9969 - 9973][Angew. Chem., 2016, vol. 128, # 34, p. 10123 - 10127]
[4]Ma, Jiajia; Strieth-Kalthoff, Felix; Dalton, Toryn; Freitag, Matthias; Schwarz, J. Luca; Bergander, Klaus; Daniliuc, Constantin; Glorius, Frank [Chem, 2019, vol. 5, # 11, p. 2854 - 2864]

19
[ 870987-64-7 ]
[ 1762-46-5 ]
bis(2-(2,4-difluorophenyl)-5-(trifluoromethyl)pyridine)(5,5’-diethoxycarboxyl-2,2’-bipyridine)iridium(III) chloride [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 12320 - 12323

20
[ 387827-64-7 ]
iridium(III) chloride n-hydrate [ No CAS ]
[ 870987-64-7 ]

Reference： [1]Journal of the American Chemical Society,2017,vol. 139,p. 17186 - 17192

21
[ 870987-64-7 ]
[ 131380-91-1 ]
(S),Λ-Ir(2-(2,4-difluorophenyl)-5-(trifluoromethyl)pyridine)₂((S)-2-(4-isopropyl-4,5-dihydrooxazol-2-yl)phenol) [ No CAS ]
(S),Δ-Ir(2-(2,4-Difluorophenyl)-5-(trifluoromethyl)pyridine)₂((S)-2-(4-isopropyl-4,5-dihydrooxazol-2-yl)phenol) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 23% 2: 28%	With triethylamine In ethanol at 95℃; for 12h; Inert atmosphere;

Reference： [1]Skubi, Kazimer L.; Kidd, Jesse B.; Jung, Hoimin; Guzei, Ilia A.; Baik, Mu-Hyun; Yoon, Tehshik P. [Journal of the American Chemical Society, 2017, vol. 139, # 47, p. 17186 - 17192]

22
2-(2,4-difluorophenyl)-4-(trifluoromethyl)pyridine [ No CAS ]
iridium(III) chloride trihydrate [ No CAS ]
[ 870987-64-7 ]

Yield	Reaction Conditions	Operation in experiment
1.6 g	In 2-ethoxy-ethanol; water at 120℃; Inert atmosphere; Schlenk technique;

Reference： [1]Peng, Long; Li, Zheqi; Yin, Guoyin [Organic Letters, 2018, vol. 20, # 7, p. 1880 - 1883]

23
[ 144025-03-6 ]
[ 870987-64-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran / 17 h / 70 °C / Inert atmosphere; Schlenk technique 2: 2-ethoxy-ethanol; water / 120 °C / Inert atmosphere; Schlenk technique
	Multi-step reaction with 2 steps 1: PdCl(dppb)(C<SUB>3</SUB>H<SUB>5</SUB>); potassium carbonate / toluene; methanol; water / 16 h / 110 °C / Inert atmosphere; Schlenk technique 2: water; 2-ethoxy-ethanol / 24 h / 125 °C / Inert atmosphere; Schlenk technique

Reference： [1]Peng, Long; Li, Zheqi; Yin, Guoyin [Organic Letters, 2018, vol. 20, # 7, p. 1880 - 1883]
[2]Boyaala, Rabab; Peng, Marie; Tai, Wun-Shan; Touzani, Rachid; Roisnel, Thierry; Dorcet, Vincent; Chi, Yun; Guerchais, Véronique; Doucet, Henri; Soulé, Jean-François [Inorganic Chemistry, 2020, vol. 59, # 19, p. 13898 - 13911]

24
ammonium hexafluorophosphate [ No CAS ]
[ 862675-34-1 ]
[ 870987-64-7 ]
C₃₈H₂₂F₁₀IrN₆⁽¹⁺⁾*F₆P^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	Stage #1: 1-benzyl-4-(pyrid-2-yl)-1,2,3-triazole; bis-(μ)-chlorotetrakis[2-(2’,4’-difluorophenyl)-5-trifluoromethylpyridinato]-(C2,N)diiridium(III) In methanol; dichloromethane for 17h; Darkness; Inert atmosphere; Stage #2: ammonium hexafluorophosphate for 16h; Darkness; Inert atmosphere;

Reference： [1]Soulsby, Lachlan C.; Hayne, David J.; Doeven, Egan H.; Wilson, David J. D.; Agugiaro, Johnny; Connell, Timothy U.; Chen, Lifen; Hogan, Conor F.; Kerr, Emily; Adcock, Jacqui L.; Donnelly, Paul S.; White, Jonathan M.; Francis, Paul S. [Physical Chemistry Chemical Physics, 2018, vol. 20, # 28, p. 18995 - 19006]

25
[ 52334-81-3 ]
[ 144025-03-6 ]
[ 870987-64-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: triphenylphosphine; potassium carbonate; palladium diacetate / 1,2-dimethoxyethane / Inert atmosphere; Reflux 2: 2-ethoxy-ethanol; water / 120 °C

Reference： [1]Bruijn, A. Dowine De; Roelfes, Gerard [Chemistry - A European Journal, 2018, vol. 24, # 44, p. 11314 - 11318]

26
ammonium hexafluorophosphate [ No CAS ]
[ 870987-64-7 ]
[ 72914-19-3 ]
[ 676525-77-2 ]

Reference： [1]Chemistry - A European Journal,2018,vol. 24,p. 11314 - 11318

27
[ 870987-64-7 ]
4,4′-(2,2′-bipyridine-5,5′-diyl)dibenzoic acid [ No CAS ]
C₅₀H₃₀F₁₀IrN₄O₄⁽¹⁺⁾*Cl^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	In methanol; chloroform at 120℃; for 48h; Sealed tube;

Reference： [1]Zhu, Yuan-Yuan; Lan, Guangxu; Fan, Yingjie; Veroneau, Samuel S.; Song, Yang; Micheroni, Daniel; Lin, Wenbin [Angewandte Chemie - International Edition, 2018, vol. 57, # 43, p. 14090 - 14094][Angew. Chem., 2018, vol. 130, p. 14286 - 14290,5]

28
[ 387827-64-7 ]
iridium(III) chloride trihydrate [ No CAS ]
[ 870987-64-7 ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 14090 - 14094
Angew. Chem.,2018,vol. 130,p. 14286 - 14290,5

29
[ 17084-13-8 ]
[ 870987-64-7 ]
[ 72914-19-3 ]
[ 870987-63-6 ]

Reference： [1]Organic Letters,2018,vol. 20,p. 6794 - 6798
[2]Organic Letters,2019,vol. 21,p. 6668 - 6673
[3]Angewandte Chemie - International Edition,2020,vol. 59,p. 4121 - 4130
Angew. Chem.,2020,vol. 132,p. 4150 - 4159,10

30
[ 870987-64-7 ]
[ 142946-80-3 ]
[Ir(dF(CF₃)ppy)₂(5,5’-dCF₃bpy)]Cl [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 15664 - 15669
Angew. Chem.,2018,vol. 130,p. 15890 - 15895,6

31
[ 870987-64-7 ]
[ 72914-19-3 ]
[Ir(dF(CF₃)ppy)₂(dtbbpy)]Cl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	In 2-methoxy-ethanol Inert atmosphere; Sealed tube; Reflux;

Reference： [1]Rohe, Samantha; Morris, Avery O.; McCallum, Terry; Barriault, Louis [Angewandte Chemie - International Edition, 2018, vol. 57, # 48, p. 15664 - 15669][Angew. Chem., 2018, vol. 130, p. 15890 - 15895,6]

32
[ 870987-64-7 ]
6CHO₂^(1-)*4HO^(1-)*4O^(2-)*6Hf⁽⁴⁺⁾*2C₂₅H₁₃N₂O₆^(3-) [ No CAS ]
6CHO₂^(1-)*4HO^(1-)*4O^(2-)*6Hf⁽⁴⁺⁾*1.42Ir*2C₂₅H₁₃N₂O₆^(3-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In methanol at 80℃; for 48h;

Reference： [1]Lan, Guangxu; Ni, Kaiyuan; Veroneau, Samuel S.; Song, Yang; Lin, Wenbin [Journal of the American Chemical Society, 2018, vol. 140, # 49, p. 16971 - 16975]

33
[ 870987-64-7 ]
dimethyl (2,2′-bipyridine)-5,5′-dibenzoate [ No CAS ]
C₅₀H₃₀F₁₀IrN₄O₄⁽¹⁺⁾*Cl^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	In methanol; chloroform at 120℃; for 48h; Sealed tube;	7 Synthesis and characterization of Hf₁₂-QPDC-lr-F and Hf₆-BPY-lr-F: Me2QPDC-lr-F lr[dF(CF3)ppy]2CI dimer [dF(CF3)ppy = 2-(2',4'- difluorophenyl)-5-(trifluoromethyl)pyridine] and 4,4'-([2,2'-bipyridine]-5,5'- diyl)dibenzoic acid (H2QPDC) were synthesized as described previously. See Lowry et al., 2005; and Zhang et al., 2016. As shown in Scheme 10, below, lr[dF(CF3)ppy]2CI dimer (595 mg, 0.4 mmol), H2QPDC (318 mg, 0.75 mmol), methanol (20 ml_) and chloroform (20 ml_) were added to a 200 ml_ thick-walled sealed tube. The tube was sealed and heated at 120°C for 2 days. The solution gradually became clear under heating. After cooling to ambient temperature, the solvent was removed under reduced pressure and the crude product was purified by column chromatography (SiO2, CHCIs/MeOH, 10: 1 to 5: 1 ) to yield the product as a light yellow solid (570 mg, 65%). 1H NMR (500 MHz, CDCI3): 10.34 (d, J = 9.0 Hz, 2 H), 8.67 (d d, J, = 8.5 Hz, J2 = 2.5 Hz, 2 H), 8.53 (d d, J, = 9.0 Hz, J2 = 2.5 Hz, 2 H), 8.14 (d, J = 8.0 Hz, 4 H), 8.10-8.08 (m, 4 H), 7.66 (s, 2 H), 7.42 (d, J = 8.0 Hz, 4 H), 6.70 (d d d, Ji = 10.0 Hz, J2 = 9.0 Hz, J3 = 2.5 Hz, 2 H), 5.70 (d d, , = 8.0 Hz, J2 = 2.5 Hz, 2 H), 3.95 (s, 6 H). 19F NMR (470 MHz, CDCI3): £-62.72 (s, 6 H), -100.42 (d t, J, = 12.2 Hz, J2 = 8.5 Hz, 2 H), -105.44 (t, J = 12.2 Hz, 2 H). HRMS (ESI-FT) mlz Calcd. for C5oH30F10lrN4O4+([M - Cl"]+) 1 133.1731 , Found: 1 133.1744.
	In methanol; chloroform at 120℃; for 48h; Sealed tube;

Reference： [1]Current Patent Assignee: UNIVERSITY OF CHICAGO - WO2019/28250, 2019, A1 Location in patent: Page/Page column 102; 103
[2]Lan, Guangxu; Ni, Kaiyuan; Veroneau, Samuel S.; Song, Yang; Lin, Wenbin [Journal of the American Chemical Society, 2018, vol. 140, # 49, p. 16971 - 16975]

34
[ 870987-64-7 ]
4′,6′-bis(4-benzoic acid)-(2,2′-bipyridine)-5-carboxylic acid [ No CAS ]
C₄₉H₂₆F₁₀IrN₄O₆⁽¹⁺⁾*Cl^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
37%	In methanol; chloroform at 120℃; for 72h; Sealed tube;

Reference： [1]Lan, Guangxu; Ni, Kaiyuan; Veroneau, Samuel S.; Song, Yang; Lin, Wenbin [Journal of the American Chemical Society, 2018, vol. 140, # 49, p. 16971 - 16975]

35
[ 870987-64-7 ]
[ 1337570-02-1 ]
C₅₆H₅₀F₁₀IrN₄Si₂⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In 1,2-dimethoxyethane at 150℃; for 21.5h; Inert atmosphere;

Reference： [1]Neumann, Svenja; Wenger, Oliver S. [Inorganic Chemistry, 2019, vol. 58, # 1, p. 855 - 860]

36
[ 870987-64-7 ]
C₅₂H₃₇Cl₂N₃O₂ [ No CAS ]
C₇₆H₄₇Cl₂F₁₀IrN₅O₂⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	In 1,2-dimethoxyethane at 150℃; for 22h; Inert atmosphere;

Reference： [1]Neumann, Svenja; Wenger, Oliver S. [Inorganic Chemistry, 2019, vol. 58, # 1, p. 855 - 860]

37
[ 870987-64-7 ]
C₆₈H₅₃Cl₂N₃O₂ [ No CAS ]
C₉₂H₆₃Cl₂F₁₀IrN₅O₂⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41%	Stage #1: bis-(μ)-chlorotetrakis[2-(2’,4’-difluorophenyl)-5-trifluoromethylpyridinato]-(C2,N)diiridium(III); C₆₈H₅₃Cl₂N₃O₂ In 1,2-dimethoxyethane at 150℃; for 13h; Inert atmosphere; Stage #2: With silver nitrate In 1,2-dimethoxyethane for 22h; Inert atmosphere;

Reference： [1]Neumann, Svenja; Wenger, Oliver S. [Inorganic Chemistry, 2019, vol. 58, # 1, p. 855 - 860]

38
iridium(III) chloride [ No CAS ]
[ 387827-64-7 ]
[ 870987-64-7 ]

Yield	Reaction Conditions	Operation in experiment
	In 2-methoxy-ethanol; water; at 120℃;Inert atmosphere;	Heteroleptic iridium complex Ir1 was synthesized in a two-step procedure. In the first step, chloro-bridged dimer was synthesized by charging a two-necked reaction flask with magnetic stirbar, iridium (III) chloride (1 equiv), ligand (2.26 equiv), and a 2:1 v:v mixture of 2-methoxyethanol/water. The mixture was degassed with Ar and heated under reflux at 120C overnight. The reaction mixture was then cooled to room temperature and filtered. The precipitate was washed with water, dried under vacuum and taken to the second step without further purification. In the second step, the chloro bridging dimer (1 equiv), bipyridyl ligand (2.2 equiv) and ethylene glycol were placed in a two-necked flask and then flushed with Argon. The mixture was heated at 150C for 24 h and then cooled. The cooled reaction mixture was washed hexane and heated to 85C for 5 min to remove the residual hexane and aqueous ammonium hexafluorophosphate (2g for each 100 mg IrCl3) was added to the reaction mixture causing the iridium-PF6 salt to precipitate, which was filtered, purified on silica column using DCM/Hexane as eluent dried under vacuum for 6h and the Ir1 complex was isolated as yellow solid (74% yield).

Reference： [1]Tetrahedron,2019,vol. 75

39
ammonium hexafluorophosphate [ No CAS ]
[ 870987-64-7 ]
[ 72914-19-3 ]
[ 870987-63-6 ]

Yield	Reaction Conditions	Operation in experiment
74%		Heteroleptic iridium complex Ir1 was synthesized in a two-step procedure. In the first step, chloro-bridged dimer was synthesized by charging a two-necked reaction flask with magnetic stirbar, iridium (III) chloride (1 equiv), ligand (2.26 equiv), and a 2:1 v:v mixture of 2-methoxyethanol/water. The mixture was degassed with Ar and heated under reflux at 120C overnight. The reaction mixture was then cooled to room temperature and filtered. The precipitate was washed with water, dried under vacuum and taken to the second step without further purification. In the second step, the chloro bridging dimer (1 equiv), bipyridyl ligand (2.2 equiv) and ethylene glycol were placed in a two-necked flask and then flushed with Argon. The mixture was heated at 150C for 24 h and then cooled. The cooled reaction mixture was washed hexane and heated to 85C for 5 min to remove the residual hexane and aqueous ammonium hexafluorophosphate (2g for each 100 mg IrCl3) was added to the reaction mixture causing the iridium-PF6 salt to precipitate, which was filtered, purified on silica column using DCM/Hexane as eluent dried under vacuum for 6h and the Ir1 complex was isolated as yellow solid (74% yield).

Reference： [1]Tetrahedron,2019,vol. 75

40
[ 870987-64-7 ]
dimethyl (2,2′-bipyridine)-5,5′-dibenzoate [ No CAS ]
C₅₀H₃₀F₁₀IrN₄O₄⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; chloroform at 120℃; for 48h;

Reference： [1]Quan, Yangjian; Lan, Guangxu; Fan, Yingjie; Shi, Wenjie; You, Eric; Lin, Wenbin [Journal of the American Chemical Society, 2020, vol. 142, # 4, p. 1746 - 1751]

41
[ 870987-64-7 ]
[ 72914-19-3 ]
[Ir(C₆H₂F₂-C₅H₃NCF₃)₂(4,4′-di-tert-butyl-2,2′-dipyridyl)]⁺ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dimethyl sulfoxide at 150℃; Sealed tube;

Reference： [1]Bernhard, Stefan; Connell, Timothy U.; Diluzio, Stephen; Kowalewski, Jakub F.; Kowalewski, Tomasz; Lewis, Jacqueline; Mdluli, Velabo; Yaron, David [ACS Catalysis, 2020, vol. 10, # 13, p. 6977 - 6987]

42
2-(2,4-difluorophenyl)-4-(trifluoromethyl)pyridine [ No CAS ]
iridium(III) chloride monohydrate [ No CAS ]
[ 870987-64-7 ]

Yield	Reaction Conditions	Operation in experiment
	In 2-ethoxy-ethanol; water at 135℃; for 40h; Inert atmosphere;

Reference： [1]Knowles, Robert R.; Metrano, Anthony J.; Tsuchiya, Yuto; Tsui, Elaine [Angewandte Chemie - International Edition, 2020, vol. 59, # 29, p. 11845 - 11849][Angew. Chem.]

43
[ 870987-64-7 ]
[Ir(2-(2,4-difluorophenyl)-4-(trifluoromethyl)pyridine)₂(5,5'-bis(trifluoromethyl)-2,2'-bipyridine)]PF₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: dichloromethane; acetonitrile / 55 °C / Inert atmosphere; Glovebox 2: dichloromethane; ethanol / 40 °C / Inert atmosphere

Reference： [1]Knowles, Robert R.; Metrano, Anthony J.; Tsuchiya, Yuto; Tsui, Elaine [Angewandte Chemie - International Edition, 2020, vol. 59, # 29, p. 11845 - 11849][Angew. Chem.]

44
[ 26042-63-7 ]
[ 870987-64-7 ]
8,8-diacetonitrile-11,11',13,13'-tetrafluoro-5,5'-bis(trifluoromethyl)-7λ,7'λ-diaza-8-irida-8,8'-spirobi[tricyclo[7.4.0.0,]tridecane]-1(9),1'(9'),2,2',4,4',6,6',10,10',12,12'-dodecaene-8,8,8-tris(ylium)-9,9'-diuide; hexafluoro-λ-phosphane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane; acetonitrile at 55℃; Inert atmosphere; Glovebox;

Reference： [1]Knowles, Robert R.; Metrano, Anthony J.; Tsuchiya, Yuto; Tsui, Elaine [Angewandte Chemie - International Edition, 2020, vol. 59, # 29, p. 11845 - 11849][Angew. Chem.]

45
[ 387827-64-7 ]
iridium(III) chloride hexahydrate [ No CAS ]
[ 870987-64-7 ]

Yield	Reaction Conditions	Operation in experiment
	In 2-ethoxy-ethanol; water at 125℃; for 24h; Inert atmosphere; Schlenk technique;

Reference： [1]Boyaala, Rabab; Peng, Marie; Tai, Wun-Shan; Touzani, Rachid; Roisnel, Thierry; Dorcet, Vincent; Chi, Yun; Guerchais, Véronique; Doucet, Henri; Soulé, Jean-François [Inorganic Chemistry, 2020, vol. 59, # 19, p. 13898 - 13911]

46
[ 52334-81-3 ]
[ 870987-64-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: PdCl(dppb)(C<SUB>3</SUB>H<SUB>5</SUB>); potassium carbonate / toluene; methanol; water / 16 h / 110 °C / Inert atmosphere; Schlenk technique 2: water; 2-ethoxy-ethanol / 24 h / 125 °C / Inert atmosphere; Schlenk technique

47
[ 98-98-6 ]
[ 870987-64-7 ]
iridium(III) bis[2-(2,4-difluorophenyl)-5-(trifluoromethyl) pyridinato-N,C2′] picolinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With sodium carbonate In 2-ethoxy-ethanol at 125℃; for 24h; Inert atmosphere; Schlenk technique;

48
[ 1134-35-6 ]
[ 26042-63-7 ]
[ 870987-64-7 ]
iridium(III) bis[2-(2,4-difluorophenyl)-5-(trifluoromethyl)-pyridinato-N,C2′]-4,4′-dimethyl-2,2′-bipyridine hexafluorophosphate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	In dichloromethane at 20℃; for 16h; Inert atmosphere; Schlenk technique; Darkness;

49
[ 1033694-68-6 ]
[ 870987-64-7 ]
C₄₈H₄₂F₁₀IrN₄O₁₀S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	In methanol; dichloromethane at 60℃; for 16h; Inert atmosphere;

Reference： [1]van Lier, Roos C. W.; de Bruijn, A. Dowine; Roelfes, Gerard [Chemistry - A European Journal, 2021, vol. 27, # 4, p. 1430 - 1437]

50
4,4’‐bis(trimethylammoniummethyl)‐2,2’‐bipyridine [ No CAS ]
[ 870987-64-7 ]
C₄₂H₃₈F₁₀IrN₆⁽³⁺⁾*3Cl^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%	In 2-ethoxy-ethanol; water at 150℃; for 16h; Inert atmosphere;

Reference： [1]van Lier, Roos C. W.; de Bruijn, A. Dowine; Roelfes, Gerard [Chemistry - A European Journal, 2021, vol. 27, # 4, p. 1430 - 1437]

51
[ 870987-64-7 ]
dimethyl (2,2′-bipyridine)-5,5′-dibenzoate [ No CAS ]
C₅₀H₃₀F₁₀IrN₄O₄⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; chloroform at 120℃; for 48h;

Reference： [1]Nash, Geoffrey T.; Luo, Taokun; Lan, Guangxu; Ni, Kaiyuan; Kaufmann, Michael; Lin, Wenbin [Journal of the American Chemical Society, 2021, vol. 143, # 5, p. 2194 - 2199]

52
[ 870987-64-7 ]
[ 6813-38-3 ]
[ 76-05-1 ]
C₃₆H₁₈F₁₀IrN₄O₄⁽¹⁺⁾*C₂F₃O₂^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	Stage #1: bis-(μ)-chlorotetrakis[2-(2’,4’-difluorophenyl)-5-trifluoromethylpyridinato]-(C2,N)diiridium(III); 2,2'-Bipyridine-4,4'-dicarboxylic acid With sodium acetate In methanol at 75℃; for 72h; Stage #2: trifluoroacetic acid In methanol; dichloromethane

Reference： [1]Nguyen, Terrence-Thang H.; O'Brien, Connor J.; Tran, Minh L. N.; Olson, Steven H.; Settineri, Nicholas S.; Prusiner, Stanley B.; Paras, Nick A.; Conrad, Jay [Organic Letters, 2021, vol. 23, # 10, p. 3823 - 3827]

53
[ 870987-64-7 ]
[ 72914-19-3 ]
C₄₂H₃₄F₁₀IrN₄⁽¹⁺⁾*Cl^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethylene glycol at 150℃; for 16h; Inert atmosphere;

Reference： [1]Anderson, Edward A.; Mousseau, James. J.; Nugent, Jeremy; Owen, Benjamin; Pickford, Helena D.; Smith, Russell C. [Journal of the American Chemical Society, 2021, vol. 143, # 26, p. 9729 - 9736]

54
ammonium hexafluorophosphate [ No CAS ]
[ 870987-64-7 ]
[ 1375312-80-3 ]
C₆₈H₈₆F₁₀IrN₄⁽¹⁺⁾*F₆P^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
21%	Stage #1: bis-(μ)-chlorotetrakis[2-(2’,4’-difluorophenyl)-5-trifluoromethylpyridinato]-(C2,N)diiridium(III); 4-(5,9-diethyltridecan-7-yl)-4′-(5,9-diethyltridecan-7-yl)-2,2′-bipyridine for 0.0166667h; Inert atmosphere; Sonication; Stage #2: at 200℃; for 1h; Microwave irradiation; Stage #3: ammonium hexafluorophosphate Further stages;

Reference： [1]Delgado, Pete; Duvadie, Rohit; Elmaarouf, Imran; Geraci, Gina; Glass, Raoul J.; Majumdar, Dyuti; Mikus, Malte; Robinson, Richard I.; Tan, Kian L. [Journal of Organic Chemistry, 2021, vol. 86, # 23, p. 17428 - 17436]

55
[ 366-18-7 ]
[ 870987-64-7 ]
C₃₄H₁₈F₁₀IrN₄⁽¹⁺⁾*Cl^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dimethyl sulfoxide at 150℃; for 16h;

Reference： [1]Bernhard, Stefan; Connell, Timothy U.; Diluzio, Stephen; Kowalewski, Jakub F.; Mdluli, Velabo [Journal of the American Chemical Society, 2022, vol. 144, # 3, p. 1431 - 1444]

56
[ 870987-64-7 ]
(3'-([2,2'-bipyridin]-5-yl)-2',6'-dimethoxy-[1,1'-biphenyl]-2-yl) dicyclohexylphosphonium tetrafluoroborate [ No CAS ]
C₆₀H₅₁F₁₀IrN₄O₂P⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	In ethylene glycol at 120℃; for 4h; Inert atmosphere;

Reference： [1]Chia, Xiu Li; Li, Mingfeng; Zhu, Ye [Chemical Communications, 2022, vol. 58, # 30, p. 4719 - 4722]

57
tetrabutylammonium hexafluorophosphate [ No CAS ]
[ 870987-64-7 ]
4,4′-bis[(trimethylammonino)methyl]-2,2′-bipyridine bis(hexafluorophosphate) [ No CAS ]
bis[3,5-difluoro-2-[(5-trifluoromethyl-2-pyridinyl-κN)phenyl-κC](4,4'-bis[(trimethylammonino)methyl]-2,2'-bipyridine)]iridium(III) tri(hexafluorophosphate) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%	Stage #1: [(dF(CF₃)ppy)₂-Ir-μ-Cl]₂; 4,4′-bis[(trimethylammonino)methyl]-2,2′-bipyridine bis(hexafluorophosphate) In methanol at 90℃; for 1h; Microwave irradiation; Autoclave; Stage #2: tetrabutylammonium hexafluorophosphate In MeCN; lithium hydroxide monohydrate

Reference： [1]Deetz, Alexander M.; Meyer, Gerald J. [Journal of the American Chemical Society, 2022, vol. 2, # 4, p. 985 - 995]

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Response
Code	Phrase
P301	IF SWALLOWED:
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P320
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P321
P322
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P335	Brush off loose particles from skin.
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P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
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P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
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P401
P402	Store in a dry place.
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P413
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P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
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P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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H204	Fire or projection hazard
H205	May mass explode in fire
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H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
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H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
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H320	Causes eye irritation
H330	Fatal if inhaled
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H332	Harmful if inhaled
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H340	May cause genetic defects
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H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 870987-64-7 ] {[proInfo.proName]}

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[ 870987-64-7 ] Synthesis Path-Upstream 1~3

[ 870987-64-7 ] Synthesis Path-Downstream 1~57

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