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Chemical Structure| 870259-02-2
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Product Details of [ 870259-02-2 ]

CAS No. :870259-02-2 MDL No. :MFCD21609448
Formula : C24H10 Boiling Point : -
Linear Structure Formula :- InChI Key :KSGRPWUUBFXSMB-UHFFFAOYSA-N
M.W : 298.34 Pubchem ID :11630783
Synonyms :

Safety of [ 870259-02-2 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 870259-02-2 ]

* 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.

  • Downstream synthetic route of [ 870259-02-2 ]

[ 870259-02-2 ] Synthesis Path-Downstream   1~55

  • 1
  • [ 870258-96-1 ]
  • [ 870259-02-2 ]
YieldReaction ConditionsOperation in experiment
100% With potassium hydroxide; water In methanol; dichloromethane at 20℃; for 0.666667h;
97.6% With water; potassium hydroxide In tetrahydrofuran at 20℃; for 12h;
97% With potassium carbonate In methanol at 20℃; for 16h;
97% With potassium hydroxide In tetrahydrofuran at 20℃; Inert atmosphere; 1.2 (2) Synthesis of intermediates of chemical structure b: (587 mg, 1 mmol) intermediate compound a, (448 mg, 8 mmol) potassium hydroxide, 50 mL THF,Add to the reaction flask, protect with N2 and stir at room temperature overnight, the reaction is completed.Pour it into 500 mL of water and sediment by suction to obtain pale yellow solid particles.That is, intermediate compound b, the yield was 97%.
95% With potassium carbonate In methanol
95% With potassium carbonate In methanol
94.3% With methanol; potassium carbonate at 20℃; for 48h;
93% With tetrabutyl ammonium fluoride In tetrahydrofuran at 35℃; for 1h;
93% With methanol; potassium hydroxide In water; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran at 20℃; for 1h; Preparation of 1,3,6,8-tetraethynylpyrene (12) A mixture of 1,3,6,8-tetrakis(trimethylsilylethynyl)pyrene (3, 1.761 g, 3.0 mmol), KOH (1.458 g, 26 mmol), H2O (26 mL), MeOH (30 mL), CH2Cl2 (30 mL) was stirred at room temperature for 1 h. The solution was concentrated in vacuo. H2O (100 mL) was added. The solid was collected by suction filtration with H2O (90 mL) to give tetraethynylpyrene (12, yellow solid, 831 mg, 93% yield).
75.7% With potassium carbonate In tetrahydrofuran; methanol at 20℃; for 1h; Inert atmosphere;
73% With potassium hydroxide In tetrahydrofuran; methanol at 20℃; for 1h;
With water; potassium hydroxide In methanol; dichloromethane for 12h;
With tetrabutyl ammonium fluoride In tetrahydrofuran at 0℃; for 0.166667h; Inert atmosphere;
51 mg With methanol; potassium carbonate

Reference: [1]Location in patent: scheme or table Lianes-Pallas, Anna; Prato, Maurizio; Bonifazi, Davide; Palma, Carlos-Andres; Piot, Luc; Samori, Paolo; Belbakra, Abdelhalim; Listorti, Andrea; Armaroli, Nicola [Journal of the American Chemical Society, 2009, vol. 131, # 2, p. 509 - 520]
[2]Location in patent: experimental part Hirose, Takuji; Shibano, Yuki; Miyazaki, Yutaro; Sogoshi, Norihito; Nakabayashi, Seiichiro; Yasutake, Mikio [Molecular Crystals and Liquid Crystals, 2011, vol. 534, p. 81 - 92]
[3]Cappellari, Maria V.; Mangione, María I.; Spanevello, Rolando A.; Marzari, Gabriela; Morales, Gustavo M.; Fungo, Fernando [Journal of the Electrochemical Society, 2018, vol. 165, # 14, p. G163 - G170]
[4]Current Patent Assignee: XIANGTAN UNIVERSITY - CN109762006, 2019, A Location in patent: Paragraph 0035; 0037; 0040; 0041
[5]Bernhardt, Stefan; Kastler, Marcel; Enkelmann, Volker; Baumgarten, Martin; Muellen, Klaus [Chemistry - A European Journal, 2006, vol. 12, # 23, p. 6117 - 6128]
[6]Xu, Yunfeng; Chang, Dan; Feng, Shi; Zhang, Chong; Jiang, Jia-Xing [New Journal of Chemistry, 2016, vol. 40, # 11, p. 9415 - 9423]
[7]Mohamed, Mohamed Gamal; Elsayed, Mohamed Hammad; Elewa, Ahmed M.; EL-Mahdy, Ahmed F. M.; Yang, Cheng-Han; Mohammed, Ahmed A. K.; Chou, Ho-Hsiu; Kuo, Shiao-Wei [Catalysis science and technology, 2021, vol. 11, # 6, p. 2229 - 2241]
[8]Venkataramana, Gandikota; Sankararaman, Sethuraman [European Journal of Organic Chemistry, 2005, # 19, p. 4162 - 4166]
[9]Maeda, Hajime; Shoji, Tomokazu; Segi, Masahito [Tetrahedron Letters, 2017, vol. 58, # 46, p. 4372 - 4376]
[10]Xu, Xing-Dong; Zhang, Jing; Yu, Xudong; Chen, Li-Jun; Wang, De-Xian; Yi, Tao; Li, Fuyou; Yang, Hai-Bo [Chemistry - A European Journal, 2012, vol. 18, # 50, p. 16000 - 16013]
[11]Maeda, Hajime; Tanaka, Kazuhiro; Aratani, Mona; Segi, Masahito [Photochemistry and Photobiology, 2019, vol. 95, # 3, p. 762 - 772]
[12]Location in patent: scheme or table Zeitouny, Joceline; Belbakra, Abdelhalim; Llanes-Pallas, Anna; Barbieri, Andrea; Armaroli, Nicola; Bonifazi, Davide [Chemical Communications, 2011, vol. 47, # 1, p. 451 - 453]
[13]Yang, Liang-Liang; Wang, Hong-Juan; Wang, Juan; Li, Yu; Zhang, Wen; Lu, Tong-Bu [Journal of Materials Chemistry A, 2019, vol. 7, # 21, p. 13142 - 13148]
[14]Bian, Gao-Feng; Zhao, Feng; Lau, Tsz-Ki; Sheng, Chun-Qi; Lu, Xinhui; Du, Hui; Zhang, Cheng; Qu, Zhi-Rong; Chen, Hongzheng; Wan, Jun-Hua [Journal of Materials Chemistry C, 2019, vol. 7, # 26, p. 8092 - 8100]
  • 2
  • [ 870259-02-2 ]
  • [ 38274-16-7 ]
  • 1,3,6,8--(trimethylsilylethynyl)phenyl]ethynyl}pyrene [ No CAS ]
YieldReaction ConditionsOperation in experiment
10% With copper(l) iodide; diisopropylamine; triphenylphosphine In tetrahydrofuran at 70℃; for 15h;
  • 3
  • [ 870259-02-2 ]
  • [ 212752-04-0 ]
  • C72H58O8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With copper(l) iodide; triethylamine at 50℃; for 4h;
  • 4
  • [ 870259-02-2 ]
  • [ 479-33-4 ]
  • C136H90 [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With o-xylene at 160℃; for 12h;
  • 5
  • [ 129-00-0 ]
  • [ 870259-02-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: bromine / nitrobenzene / 3 h / 160 °C 2: 83 percent / copper(I) iodide; triphenylphosphine / bis(triphenylphosphine)palladium(II)dichloride / triethylamine; toluene / 60 - 80 °C 3: 95 percent / K2CO3 / methanol
Multi-step reaction with 3 steps 1: 94 percent / bromine / nitrobenzene / 4 h / 120 °C 2: 33 percent / CuI; PPh3; diisopropylamine / [PdCl2(PPh3)2] / tetrahydrofuran / 12 h / 65 °C 3: 93 percent / nBu4NF / tetrahydrofuran / 1 h / 35 °C
  • 6
  • [ 128-63-2 ]
  • [ 870259-02-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 83 percent / copper(I) iodide; triphenylphosphine / bis(triphenylphosphine)palladium(II)dichloride / triethylamine; toluene / 60 - 80 °C 2: 95 percent / K2CO3 / methanol
Multi-step reaction with 2 steps 1: 33 percent / CuI; PPh3; diisopropylamine / [PdCl2(PPh3)2] / tetrahydrofuran / 12 h / 65 °C 2: 93 percent / nBu4NF / tetrahydrofuran / 1 h / 35 °C
Multi-step reaction with 2 steps 1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; diisopropylamine; triphenylphosphine / tetrahydrofuran / 12 h / 80 °C 2: water; potassium hydroxide / methanol; dichloromethane / 12 h
Multi-step reaction with 2 steps 1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; diisopropylamine; triphenylphosphine / tetrahydrofuran / 20 h / 50 °C / Inert atmosphere 2: water; potassium hydroxide / tetrahydrofuran / 12 h / 20 °C
Multi-step reaction with 2 steps 1: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; diethylamine / 39 h / 65 °C / Inert atmosphere 2: potassium carbonate / tetrahydrofuran; methanol / 1 h / 20 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; triethylamine / toluene / 60 - 80 °C / Inert atmosphere 2: potassium carbonate / methanol
Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triphenylphosphine; diisopropylamine / tetrahydrofuran / 12 h / 80 °C 2: potassium hydroxide; methanol / water; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran / 1 h / 20 °C
Multi-step reaction with 2 steps 1: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triphenylphosphine / toluene / 16 h / 80 °C 2: potassium carbonate / methanol / 16 h / 20 °C
Multi-step reaction with 2 steps 1: copper(l) iodide; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride; diisopropylamine / tetrahydrofuran / Reflux 2: potassium hydroxide / tetrahydrofuran; methanol / 1 h / 20 °C
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); triphenylphosphine; copper(l) iodide; triethylamine / toluene / 48 h / 50 - 90 °C / Inert atmosphere 2: potassium carbonate; methanol / 48 h / 20 °C

Reference: [1]Bernhardt, Stefan; Kastler, Marcel; Enkelmann, Volker; Baumgarten, Martin; Muellen, Klaus [Chemistry - A European Journal, 2006, vol. 12, # 23, p. 6117 - 6128]
[2]Venkataramana, Gandikota; Sankararaman, Sethuraman [European Journal of Organic Chemistry, 2005, # 19, p. 4162 - 4166]
[3]Zeitouny, Joceline; Belbakra, Abdelhalim; Llanes-Pallas, Anna; Barbieri, Andrea; Armaroli, Nicola; Bonifazi, Davide [Chemical Communications, 2011, vol. 47, # 1, p. 451 - 453]
[4]Hirose, Takuji; Shibano, Yuki; Miyazaki, Yutaro; Sogoshi, Norihito; Nakabayashi, Seiichiro; Yasutake, Mikio [Molecular Crystals and Liquid Crystals, 2011, vol. 534, p. 81 - 92]
[5]Xu, Xing-Dong; Zhang, Jing; Yu, Xudong; Chen, Li-Jun; Wang, De-Xian; Yi, Tao; Li, Fuyou; Yang, Hai-Bo [Chemistry - A European Journal, 2012, vol. 18, # 50, p. 16000 - 16013]
[6]Xu, Yunfeng; Chang, Dan; Feng, Shi; Zhang, Chong; Jiang, Jia-Xing [New Journal of Chemistry, 2016, vol. 40, # 11, p. 9415 - 9423]
[7]Maeda, Hajime; Shoji, Tomokazu; Segi, Masahito [Tetrahedron Letters, 2017, vol. 58, # 46, p. 4372 - 4376]
[8]Cappellari, Maria V.; Mangione, María I.; Spanevello, Rolando A.; Marzari, Gabriela; Morales, Gustavo M.; Fungo, Fernando [Journal of the Electrochemical Society, 2018, vol. 165, # 14, p. G163 - G170]
[9]Maeda, Hajime; Tanaka, Kazuhiro; Aratani, Mona; Segi, Masahito [Photochemistry and Photobiology, 2019, vol. 95, # 3, p. 762 - 772]
[10]Mohamed, Mohamed Gamal; Elsayed, Mohamed Hammad; Elewa, Ahmed M.; EL-Mahdy, Ahmed F. M.; Yang, Cheng-Han; Mohammed, Ahmed A. K.; Chou, Ho-Hsiu; Kuo, Shiao-Wei [Catalysis science and technology, 2021, vol. 11, # 6, p. 2229 - 2241]
  • 7
  • [ 870259-02-2 ]
  • [ 952308-21-3 ]
  • 1,3,6,8-tetrakis((7-((4-(3,6-di-tert-butyl-9H-carbazol-9-yl)phenyl)ethynyl)-9,9-diheptyl-9H-fluoren-2-yl)ethynyl)pyrene [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine for 4h; Inert atmosphere; Reflux;
  • 8
  • [ 870259-02-2 ]
  • [ 952308-24-6 ]
  • 1,3,6,8-tetrakis((7-((7-((4-(3,6-di-tert-butyl-9H-carbazol-9-yl)phenyl)ethynyl)-9,9-diheptyl-9H-fluoren-2-yl)ethynyl)-9,9-diheptyl-9H-fluoren-2-yl)ethynyl)pyrene [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine for 4h; Inert atmosphere; Reflux;
  • 9
  • [ 870259-02-2 ]
  • 4,4'-(9-(4-((9,9-diheptyl-7-iodo-9H-fluoren-2-yl)ethynyl)phenyl)-9H-carbazole-3,6-diyl)bis(2-methylbut-3-yn-2-ol) [ No CAS ]
  • 4,4',4'',4''',4'''',4'''''-(9,9',9''-(4,4',4''-(7,7',7''-(8-((7-((4-(3,6-bis(3-hydroxy-3-methylbut-1-ynyl)-9H-carbazol-9-yl)phenyl)ethynyl)-9,9-diheptyl-9H-fluoren-2-yl)ethynyl)pyrene-1,3,6-triyl)tris(ethyne-2,1-diyl)tris(9,9-diheptyl-9H-fluorene-7,2-diyl))tris(ethyne-2,1-diyl)tris(4,1-phenylene))tris(9H-carbazole-9,6,3-triyl))hexakis(2-methylbut-3-yn-2-ol) [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine for 4h; Inert atmosphere; Reflux;
  • 10
  • [ 870259-02-2 ]
  • [ 1092577-67-7 ]
  • 1,3,6,8-tetrakis((7-((4-(3,6-bis((7-((4-(3,6-di-tert-butyl-9H-carbazol-9-yl)phenyl)ethynyl)-9,9-diheptyl-9H-fluoren-2-yl)ethynyl)-9H-carbazol-9-yl)phenyl)ethynyl)-9,9-diheptyl-9H-fluoren-2-yl)ethynyl)pyrene [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine for 4h; Inert atmosphere; Reflux;
  • 11
  • [ 870259-02-2 ]
  • [ 1091632-52-8 ]
  • [ 1101876-78-1 ]
YieldReaction ConditionsOperation in experiment
46% With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In tetrahydrofuran at 45℃; Inert atmosphere;
  • 12
  • [ 870259-02-2 ]
  • [ 90134-09-1 ]
  • [ 1262500-77-5 ]
YieldReaction ConditionsOperation in experiment
37% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 45℃; Inert atmosphere;
  • 13
  • [ 870259-02-2 ]
  • [ 1092585-30-2 ]
  • [ 1263382-31-5 ]
YieldReaction ConditionsOperation in experiment
91% In o-xylene at 170℃; for 2h; Microwave irradiation; Inert atmosphere;
  • 14
  • [ 870259-02-2 ]
  • [ 7332-00-5 ]
  • [ 1313017-28-5 ]
YieldReaction ConditionsOperation in experiment
92% With copper(ll) sulfate pentahydrate; sodium L-ascorbate In tetrahydrofuran; water at 70℃; for 12h; Inert atmosphere;
  • 15
  • [ 870259-02-2 ]
  • [ 1337985-15-5 ]
  • 1,3,6,8-tetrakis[3,5-bis(dimethylpentylsilylethynyl)phenylethynyl]pyrene [ No CAS ]
YieldReaction ConditionsOperation in experiment
26.2% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine; triphenylphosphine In toluene at 50℃; for 48h; Inert atmosphere;
  • 16
  • [ 870259-02-2 ]
  • [ 1337985-16-6 ]
  • 1,3,6,8-tetrakis[3,5-bis(dimethylhexylsilylethynyl)phenylethynyl]pyrene [ No CAS ]
YieldReaction ConditionsOperation in experiment
8.1% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine; triphenylphosphine In toluene at 50℃; for 48h; Inert atmosphere;
  • 17
  • [ 870259-02-2 ]
  • [ 1337985-17-7 ]
  • 1,3,6,8-tetrakis[3,5-bis(dimethylheptylsilylethynyl)phenylethynyl]pyrene [ No CAS ]
YieldReaction ConditionsOperation in experiment
10.1% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine; triphenylphosphine In toluene at 50℃; for 48h; Inert atmosphere;
  • 18
  • [ 870259-02-2 ]
  • [ 1337985-18-8 ]
  • 1,3,6,8-tetrakis[3,5-bis(dimethyloctylsilylethynyl)phenylethynyl]pyrene [ No CAS ]
YieldReaction ConditionsOperation in experiment
19.3% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine; triphenylphosphine In toluene at 50℃; for 48h; Inert atmosphere;
  • 19
  • [ 870259-02-2 ]
  • 1,3,6,8-tetrakis((2-(2,2-dibromovinyl)-5-t-butylphenyl)ethynyl)pyrene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine / 0.25 h / 20 °C / Inert atmosphere 1.2: 4 h / 50 °C / Inert atmosphere 2.1: triphenylphosphine / benzene / 8 h / Inert atmosphere; Reflux
  • 20
  • [ 870259-02-2 ]
  • C72H58 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine / 0.25 h / 20 °C / Inert atmosphere 1.2: 4 h / 50 °C / Inert atmosphere 2.1: triphenylphosphine / benzene / 8 h / Inert atmosphere; Reflux 3.1: n-butyllithium
  • 21
  • [ 870259-02-2 ]
  • [ 246139-77-5 ]
  • 1,3,6,8-tetrakis(2-formyl-5-t-butylphenylethynyl)pyrene [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% Stage #1: 2-bromo-4-(tert-butyl)benzaldehyde With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine at 20℃; for 0.25h; Inert atmosphere; Stage #2: 1,3,6,8-tetraethynylpyrene at 50℃; for 4h; Inert atmosphere;
  • 22
  • [ 870259-02-2 ]
  • [ 15636-79-0 ]
  • [ 1414878-93-5 ]
YieldReaction ConditionsOperation in experiment
32% With copper(l) iodide In tetrahydrofuran; diethylamine at 20℃; for 1h; Inert atmosphere;
  • 23
  • [ 129-00-0 ]
  • [ 870259-02-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydrogen bromide / nitrobenzene / 120 °C / Inert atmosphere 2: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; diethylamine / 39 h / 65 °C / Inert atmosphere 3: potassium carbonate / tetrahydrofuran; methanol / 1 h / 20 °C / Inert atmosphere
Multi-step reaction with 3 steps 1: bromine / nitrobenzene / 3 h / 160 °C 2: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; triethylamine / toluene / 60 - 80 °C / Inert atmosphere 3: potassium carbonate / methanol
Multi-step reaction with 3 steps 1: bromine / nitrobenzene / 12 h / 80 °C 2: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triphenylphosphine; diisopropylamine / tetrahydrofuran / 12 h / 80 °C 3: potassium hydroxide; methanol / water; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran / 1 h / 20 °C
Multi-step reaction with 3 steps 1: bromine / nitrobenzene / 4 h / 120 °C 2: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triphenylphosphine / toluene / 16 h / 80 °C 3: potassium carbonate / methanol / 16 h / 20 °C
Multi-step reaction with 3 steps 1: bromine / nitrobenzene / 20 - 80 °C 2: copper(l) iodide; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride; diisopropylamine / tetrahydrofuran / Reflux 3: potassium hydroxide / tetrahydrofuran; methanol / 1 h / 20 °C
Multi-step reaction with 3 steps 1: bromine / nitrobenzene / 4 h / 120 °C 2: tetrakis(triphenylphosphine) palladium(0); triphenylphosphine; copper(l) iodide; triethylamine / toluene / 48 h / 50 - 90 °C / Inert atmosphere 3: potassium carbonate; methanol / 48 h / 20 °C

  • 24
  • [ 870259-02-2 ]
  • [ 540-38-5 ]
  • [ 1603838-43-2 ]
YieldReaction ConditionsOperation in experiment
21% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at -4 - 20℃; for 47h; Schlenk technique; Inert atmosphere; PyrCCPhOH(4) 1,3,6,8-Tetraethynylpyrene (0.16 g, 0.54mmol), 4-iodophenol (0.87 g, 4.0mmol), [PdCl2(PPh)2] (0.051 g, 0.072mmol), and CuI (0.027 g, 0.14mmol) were added to triethylamine (8 mL) at 4 °C. After the suspension was stirred at 20 °C for 47 h, the solvent was removed under vacuum. The resulting solid was washed with chloroform and water, collected by filtration, and dried under vacuum to give PyrCCPhOH(4) as a yellowish green powder (0.074 g, 21%).
  • 25
  • [ 870259-02-2 ]
  • [ 66217-22-9 ]
  • 1,3,6,8-tetrakis((6-(n-octyloxy)naphthalene-2-yl)ethynyl)pyrene [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine In toluene at 80℃; for 48h; Schlenk technique; Inert atmosphere;
  • 26
  • [ 870259-02-2 ]
  • [ 38941-98-9 ]
  • 1,3,6,8-tetrakis(5-tert-butylbenzofuran-2-yl)pyrene [ No CAS ]
  • 27
  • [ 870259-02-2 ]
  • [ 1033366-46-9 ]
  • 2,2',2'',2'''-(pyrene-1,3,6,8-tetrayltetrakis(ethyne-2,1-diyl))tetrakis(4-tert-butylbenzene-2,1-diyl) tetraacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); potassium carbonate; diisopropylamine In tetrahydrofuran at 90℃; for 12h; Schlenk technique; Inert atmosphere;
  • 28
  • [ 870259-02-2 ]
  • [ 128318-63-8 ]
  • 2,2',2'',2'''-(pyrene-1,3,6,8-tetrayltetrakis(ethyne-2,1-diyl))tetrakis(4-tert-butylaniline) [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); potassium carbonate; diisopropylamine In tetrahydrofuran at 90℃; for 12h; Schlenk technique; Inert atmosphere;
  • 29
  • [ 870259-02-2 ]
  • [ 1372541-90-6 ]
  • C104H138N16O32 [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With copper(ll) sulfate pentahydrate; sodium L-ascorbate In water; N,N-dimethyl-formamide at 20℃; for 72h; General procedure for the synthesis of iminosugar click clusters 12: General procedure: In a similar manner as described in reference [16], to a solution of 6a or 6b and azide-armed DNJ ligand 4a (1.5 equiv/alkyne moiety) in THF under argon (solution degassed by bubbling 5 min with argon) was added a bright yellow solution of CuSO4·5H2O (15 to 20 mol %/alkyne moiety) and sodium ascorbate (30 to 40 mol %/alkyne moiety) in H2O (solution degassed by bubbling 5 min with argon) at room temperature. The colored mixture darkened rapidly and was further stirred for 16 to 20 h at room temperature. The mixture was diluted with a 2:2:1 mixture of MeCN/AcOEt/30% NH4OH and filtered through a pad of silica gel, using the same mixture as eluent (25 mL). Copper salts precipitated as a blue powder and remained at the top of the silica gel pad. The filtrate was concentrated and the crude residue was purified by flash chromatography (DCM/MeOH 100:0 to 95:5) to afford iminosugar click clusters 12a and b as red solids.
  • 30
  • [ 870259-02-2 ]
  • [ 1372541-83-7 ]
  • C104H138N16O32 [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With copper(ll) sulfate pentahydrate; sodium L-ascorbate In water; N,N-dimethyl-formamide at 80℃; for 0.833333h; Microwave irradiation; General procedure for the synthesis of iminosugar click clusters 12: General procedure: In a similar manner as described in reference [16], to a solution of 6a or 6b and azide-armed DNJ ligand 4a (1.5 equiv/alkyne moiety) in THF under argon (solution degassed by bubbling 5 min with argon) was added a bright yellow solution of CuSO4·5H2O (15 to 20 mol %/alkyne moiety) and sodium ascorbate (30 to 40 mol %/alkyne moiety) in H2O (solution degassed by bubbling 5 min with argon) at room temperature. The colored mixture darkened rapidly and was further stirred for 16 to 20 h at room temperature. The mixture was diluted with a 2:2:1 mixture of MeCN/AcOEt/30% NH4OH and filtered through a pad of silica gel, using the same mixture as eluent (25 mL). Copper salts precipitated as a blue powder and remained at the top of the silica gel pad. The filtrate was concentrated and the crude residue was purified by flash chromatography (DCM/MeOH 100:0 to 95:5) to afford iminosugar click clusters 12a and b as red solids.
  • 31
  • [ 870259-02-2 ]
  • [ 925692-73-5 ]
  • C92H110N4O8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% With triethylamine In dichloromethane
  • 32
  • [ 870259-02-2 ]
  • neopentyl 4-(3-oxo-2,4-diphenyl-5-(4-propylphenyl)cyclopenta-1,4-dien-1-yl)benzenesulfonate [ No CAS ]
  • C168H154O12S4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% In o-xylene at 145℃; for 48h; Inert atmosphere; Sealed tube; Microwave irradiation;
In o-xylene at 175℃; for 24h;
  • 33
  • [ 870259-02-2 ]
  • C42H46O7S2 [ No CAS ]
  • C188H194O24S8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In o-xylene at 175℃; for 24h;
  • 34
  • [ 870259-02-2 ]
  • C36H35O4P [ No CAS ]
  • C164H150O12P4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In o-xylene at 175℃; for 24h;
  • 35
  • [ 870259-02-2 ]
  • C40H44O7P2 [ No CAS ]
  • C180H186O24P8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In o-xylene at 175℃; for 24h;
  • 36
  • [ 870259-02-2 ]
  • C34H28O3 [ No CAS ]
  • C156H122O8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In o-xylene at 175℃; for 24h;
  • 37
  • [ 870259-02-2 ]
  • C36H30O5 [ No CAS ]
  • C164H130O16 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In o-xylene at 175℃; for 24h;
  • 38
  • [ 870259-02-2 ]
  • [ 1066-35-9 ]
  • 1,3,6,8-tetrakis(dimethylsilylethynyl)pyrene [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% Stage #1: 1,3,6,8-tetraethynylpyrene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: dimethylmonochlorosilane In tetrahydrofuran; hexane at 30℃; for 21h; Preparation of 1,3,6,8-tetrakis(dimethylsilylethynyl)pyrene (2) To a stirred THF (40 mL) solution of 1,3,6,8-tetraethynylpyrene (12, 632 mg, 2.12 mmol) was slowly added n-BuLi (1.6 M in hexane, 6.5 mL, 10.4 mmol) at -78°C, and the solution was stirred at -78°C for 1 h. To the solution was added Me2HSiCl (2.4 mL, 21.6 mmol), and the solution was stirred at 30°C for 21 h. To the solution was added H2O (5.0 mL). CHCl3 (150 mL) and sat NaCl aq (120 mL) were added and shaken. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. Purification by silica gel column chromatography (eluent; hexane) gave 1,3,6,8-tetrakis(dimethylsilylethynyl)pyrene (2, 635 mg, 56% yield). Reddish orange solid; mp 152°C (dec.); 1H NMR (400 MHz, CDCl3) δ 0.46 (s, 24H), 4.42-4.45 (m, 4H), 8.33 (s, 2H), 8.63 (s, 4H) ppm; 13C NMR (100 MHz, CDCl3) δ -2.6, 98.8, 104.2, 118.7, 123.7, 127.4, 132.5, 134.8 ppm; MS (FAB) m/z (relative intensity, %) 73 (100), 147 (71), 221 (44), 281 (24), 399 (10), 530 (20, M+).
  • 39
  • [ 870259-02-2 ]
  • [ 18162-48-6 ]
  • 1,3,6,8-tetrakis(tert-butyldimethylsilylethynyl)pyrene [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% Stage #1: 1,3,6,8-tetraethynylpyrene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: tert-butyldimethylsilyl chloride In tetrahydrofuran; hexane at 70℃; for 21h; Preparation of 1,3,6,8-tetrakis(tert-butyldimethylsilylethynyl)pyrene (4) To a stirred THF (20 mL) solution of 1,3,6,8-tetraethynylpyrene (12, 120 mg, 0.4 mmol) was slowly added n-BuLi (1.6 M in hexane, 1.23 mL, 2.0 mmol) at -78°C, and the solution was stirred at -78°C for 1 h. To the solution was added t-BuMe2SiCl (290 mg, 1.9 mmol), and the solution was stirred at 70°C for 21 h. To the solution was added H2O (5.0 mL). Et2O (150 mL) and sat NaCl aq (100 mL) were added and shaken. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. Purification by silica gel column chromatography (eluent; CHCl3 : hexane = 1 : 1) gave 1,3,6,8-tetrakis(tert-butyldimethylsilylethynyl)pyrene (4, 136 mg, 45% yield). Reddish orange solid; mp 180°C (dec.); 1H NMR (400 MHz, CDCl3) δ 0.32 (s, 24H), 1.10 (s, 36H), 8.23 (s, 2H), 8.62 (s, 4H) ppm; 13C NMR (100 MHz, CDCl3) δ -4.1, 17.1, 26.6, 100.2, 103.7, 119.0, 123.9, 127.2, 132.3, 134.9 ppm; 29Si NMR (100 MHz, CDCl3) δ -7.4 ppm; IR (KBr) 2147, 2955 cm-1; MS (FAB) m/z (relative intensity, %) 73 (100), 107 (13), 136 (35), 207 (11), 754 (21, M+); HRMS (FAB) calcd for C48H67Si4: 755.4320, found: 755.4311.
  • 40
  • [ 870259-02-2 ]
  • [ 13154-24-0 ]
  • 1,3,6,8-tetrakis(triisopropylsilylethynyl)pyrene [ No CAS ]
YieldReaction ConditionsOperation in experiment
4% Stage #1: 1,3,6,8-tetraethynylpyrene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: triisopropylsilyl chloride In tetrahydrofuran; hexane for 21h; Reflux; Preparation of 1,3,6,8-tetrakis(triisopropylsilylethynyl)pyrene (5) To a stirred THF (40 mL) solution of 1,3,6,8-tetraethynylpyrene (12, 298 mg, 1.0 mmol) was slowly added n-BuLi (1.6 M in hexane, 3.1 mL, 5.0 mmol) at -78°C, and the solution was stirred at -78°C for 1 h. To the solution was added i-Pr3SiCl (1.02 mL, 4.8 mmol), and the solution was stirred at reflux for 21 h. To the solution was added H2O (5.0 mL). CHCl3 (120 mL) and sat NaCl aq (100 mL) were added and shaken. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. Purification by silica gel column chromatography (eluent; hexane : CHCl3 = 1 : 2) followed by recyclic preparative HPLC (GPC, eluent; CHCl3) gave 1,3,6,8-tetrakis(triisopropylsilylethynyl)pyrene (5, 33 mg, 4% yield). Lit.S3 Yellow solid; mp 235°C (dec.); 1H NMR (400 MHz, CDCl3) δ 1.24-1.29 (m, 84H), 8.29 (s, 2H), 8.67 (s, 4H) ppm; 13C NMR (100 MHz, CDCl3) δ 1.3, 11.8, 19.5, 98.5, 105.0, 119.3, 127.3, 132.4, 134.8, 132.3, 134.9 ppm; MS (FAB+) m/z (relative intensity, %) 136 (90), 154 (100), 307 (23), 924 (9, M++1)
  • 41
  • [ 870259-02-2 ]
  • [ 768-33-2 ]
  • 1,3,6,8-tetrakis(dimethylphenylsilylethynyl)pyrene [ No CAS ]
YieldReaction ConditionsOperation in experiment
14% Stage #1: 1,3,6,8-tetraethynylpyrene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: phenyldimethylsilyl chloride In tetrahydrofuran; hexane at 70℃; for 21h; Preparation of 1,3,6,8-tetrakis(dimethylphenylsilylethynyl)pyrene (6) To a stirred THF (25 mL) solution of 1,3,6,8-tetraethynylpyrene (12, 298 mg, 1.0 mmol) was slowly added n-BuLi (1.6 M in hexane, 3.075 mL, 4.9 mmol) at -78°C, and the solution was stirred at -78°C for 1 h. To the solution was added PhMe2SiCl (0.8 mL, 4.8 mmol), and the solution was stirred at 70°C for 21 h. To the solution was added H2O (5.0 mL). Et2O (180 mL) and sat NaCl aq (100 mL) were added and shaken. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. Purification by silica gel column chromatography (eluent; CHCl3 : hexane = 1 : 10) gave 1,3,6,8-tetrakis(dimethylphenylsilylethynyl)pyrene (6, 117 mg, 14% yield). Reddish orange solid; mp 118°C (dec.); 1H NMR (400 MHz, CDCl3) δ 0.63 (s, 24H), 7.44-7.80 (m, 20H), 8.39 (s, 2H), 8.64 (s, 4H) ppm; 13C NMR(100 MHz, CDCl3) δ -1.1, 99.2, 103.9, 118.9, 123.2, 126.8, 127.6, 131.9, 133.4, 134.3, 136.3 ppm; 29Si NMR (100 MHz, CDCl3) δ -21.1 ppm; IR (KBr) 2149, 3047 cm-1; MS (FAB) m/z (relative intensity, %) 73 (10), 107 (10), 135 (100), 834 (37, M+); HRMS (FAB) calcd for C56H51Si4: 835.3068, found 835.3065.
  • 42
  • [ 870259-02-2 ]
  • [ 2372-33-0 ]
  • 1,3,6,8-tetrakis(dimethyl(p-methoxyphenyl)silylethynyl)pyrene [ No CAS ]
YieldReaction ConditionsOperation in experiment
6% Stage #1: 1,3,6,8-tetraethynylpyrene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: chlorodimethyl(4-methoxyphenyl)silane In tetrahydrofuran; hexane at 30℃; for 21h; Preparation of 1,3,6,8-tetrakis(dimethyl-p-methoxyphenylsilylethynyl)pyrene (7) To a stirred Mg (730 mg, 30 mmol) was added dropwise THF (20 mL) solution of 4-bromoanisole (3.7 mL, 30 mmol), and the solution was stirred for 2 h at room temperature. To the solution was slowly added THF (10 mL) solution of Me2SiHCl (3.3 mL, 30 mmol), and the solution was stirred for 10 h at room temperature. To the solution was added sat NH4Cl aq. Purification by silica gel column chromatography (eluent; CHCl3) gave p-MeOC6H4Me2SiH (colorless oil, 3.242 g, 65% yield). A mixture of p-MeOC6H4Me2SiH (3.258 g, 20 mmol), PdCl2 (363 mg, 10 mol%), CCl4 (20 mL) was stirred at 80°C for 24 h. Distillation under reduced pressure gave p-MeOC6H4Me2SiCl (bp 110°C / 0.5 mmHg, colorless oil, 2.4 g, 61% yield). To a stirred THF (40 mL) solution of 1,3,6,8-tetraethynylpyrene (12, 453 mg, 1.5 mmol) was slowly added n-BuLi (1.6 M in hexane, 4.8 mL, 7.7 mmol) at -78°C, and the solution was stirred at -78°C for 1 h. To the solution was added p-MeOC6H4Me2SiCl (1.445 g, 7.2 mmol), and the solution was stirred at 30°C for 21 h. To the solution was added H2O (10 mL). CHCl3 (140 mL) and sat NaCl aq (100 mL) were added and shaken. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. Purification by silica gel column chromatography (eluent; hexane : CHCl3 = 1 : 2) gave 1,3,6,8-tetrakis(dimethyl-p-methoxyphenylsilylethynyl)pyrene (7, 86 mg, 6% yield). Reddish orange solid; mp 109-110°C; 1H NMR (400 MHz, CDCl3) δ 0.61 (s, 24H), 3.84 (s, 12H), 6.99-7.73 (m, 16H), 8.37 (s, 2H), 8.64 (s, 4H) ppm; 13C NMR(100 MHz, CDCl3) δ -0.5, 55.1, 99.9, 104.1, 113.8, 118.6, 123.6, 127.2, 127.6, 132.2, 134.7, 135.3, 160.9 ppm; 29Si NMR (100 MHz, CDCl3) δ -21.5 ppm; MS (FAB) m/z (relative intensity, %) 73 (24), 165 (100), 257 (11), 954 (43, M+).
  • 43
  • [ 870259-02-2 ]
  • [ 60457-98-9 ]
  • 1,3,6,8-tetrakis[dimethyl(p-(trifluoromethyl)phenyl)silylethynyl]pyrene [ No CAS ]
YieldReaction ConditionsOperation in experiment
7% Stage #1: 1,3,6,8-tetraethynylpyrene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: chlorodimethyl[4-(trifluoromethyl)phenyl]silane In tetrahydrofuran; hexane for 21h; Reflux; Preparation of 1,3,6,8-tetrakis[dimethyl-p-(trifluoromethyl)phenylsilylethynyl]pyrene (8) To a stirred Mg (730 mg, 30 mmol) was added dropwise THF (20 mL) solution of 4-bromobenzotrifluoride (4.2 mL, 30 mmol), and the solution was stirred for 2 h at room temperature. To the solution was slowly added THF (10 mL) solution of Me2SiHCl (3.3 mL, 30 mmol), and the solution was stirred for 10 h at room temperature. To the solution was added sat NH4Cl aq. Purification by silica gel column chromatography (eluent; hexane) gave p-F3CC6H4Me2SiH (colorless oil, 3.212 g, 52% yield). A mixture of p-F3CC6H4Me2SiH (3.212 g, 16 mmol), PdCl2 (284 mg, 10 mol%), CCl4 (15 mL) was stirred at 80°C for 24 h. Distillation under reduced pressure gave p-F3CC6H4Me2SiCl (bp 60°C / 0.5 mmHg, colorless oil, 2.154 g, 57% yield). To a stirred THF (40 mL) solution of 1,3,6,8-tetraethynylpyrene (12, 224 mg, 0.75 mmol) was slowly added n-BuLi (1.6 M in hexane, 2.4 mL, 3.8 mmol) at -78°C, and the solution was stirred at -78°C for 1 h. To the solution was added p-F3CC6H4Me2SiCl (2.154 g, 9.0 mmol), and the solution was stirred at reflux for 21 h. To the solution was added H2O (10 mL). CHCl3 (130 mL) and sat NaCl aq (100 mL) were added and shaken. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. Purification by silica gel column chromatography (eluent; hexane : CHCl3 = 1 : 2) followed by recyclic preparative HPLC (GPC, eluent; CHCl3) gave 1,3,6,8-tetrakis[dimethyl-p-(trifluoromethyl)phenylsilylethynyl]pyrene (8, 56 mg, 7% yield). Reddish orange solid; mp 156-157°C; 1H NMR (400 MHz, CDCl3) δ 0.65 (s, 24H), 7.68-7.90 (m, 16H), 8.39 (s, 2H), 8.62 (s, 4H) ppm; 13C NMR (100 MHz, CDCl3) δ -0.6, 30.0, 99.0, 105.1, 118.7, 123.9, 124.9, 127.6, 132.7, 134.4, 135.2, 141.9 ppm; 29Si NMR (100 MHz, CDCl3) δ -20.6 ppm; MS (FAB+) m/z (relative intensity, %) 147 (39), 203 (100), 281 (33), 663 (13), 865 (13), 904 (7), 1107 (47, M++1).
  • 44
  • [ 870259-02-2 ]
  • [ 144-79-6 ]
  • 1,3,6,8-tetrakis(methyldiphenylsilylethynyl)pyrene [ No CAS ]
YieldReaction ConditionsOperation in experiment
21% Stage #1: 1,3,6,8-tetraethynylpyrene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: chloromethyldiphenylsilane In tetrahydrofuran; hexane at 70℃; for 21h; Preparation of 1,3,6,8-tetrakis(methyldiphenylsilylethynyl)pyrene (9) To a stirred THF (30 mL) solution of 1,3,6,8-tetraethynylpyrene (12, 380 mg, 1.27 mmol) was slowly added n-BuLi (1.6 M in hexane, 3.91 mL, 6.3 mmol) at -78°C, and the solution was stirred at -78°C for 1 h. To the solution was added Ph2MeSiCl (1.27 mL, 6.1 mmol), and the solution was stirred at 70°C for 21 h. To the solution was added H2O (5 mL). CHCl3 (200 mL) and sat NaCl aq (100 mL) were added and shaken. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. Purification by silica gel column chromatography (eluent; CHCl3 : hexane = 1 : 3) gave 1,3,6,8-tetrakis(dimethylphenylsilylethynyl)pyrene (9, 285 mg, 21% yield). Yellow solid; mp 208°C (dec.); 1H NMR (400 MHz, CDCl3) δ 0.90 (s, 12H), 7.43-7.82 (m, 40H), 8.47 (s, 2H), 8.68 (s, 4H) ppm; 13C NMR(100 MHz, CDCl3) δ -1.8, 99.0, 105.7, 118.5, 123.5, 127.3, 128.1, 129.1, 132.5, 134.6, 135.0 ppm; 29Si NMR (100 MHz, CDCl3) δ -25.1 ppm; IR (KBr) 2149, 3048 cm-1; MS (FAB) m/z (relative intensity, %) 77 (35), 154 (100), 197 (73), 307 (15), 391 (11), 661 (12), 1083 (25, M+); HRMS (FAB) calcd for C76H59Si4: 1083.3694, found: 1083.3702.
  • 45
  • [ 870259-02-2 ]
  • [ 76-86-8 ]
  • 1,3,6,8-tetrakis(triphenylsilylethynyl)pyrene [ No CAS ]
YieldReaction ConditionsOperation in experiment
18% Stage #1: 1,3,6,8-tetraethynylpyrene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: Triphenylsilyl chloride In tetrahydrofuran; hexane at 70℃; for 21h; Preparation of 1,3,6,8-tetrakis(triphenylsilylethynyl)pyrene (10) To a stirred THF (60 mL) solution of 1,3,6,8-tetraethynylpyrene (12, 298 mg, 1.0 mmol) was slowly added n-BuLi (1.6 M in hexane, 3.075 mL, 4.9 mmol) at -78°C, and the solution was stirred at -78°C for 1 h. To the solution was added Ph3SiCl (2.949 g, 10.0 mmol), and the solution was stirred at 70°C for 21 h. To the solution was added H2O (5 mL). CHCl3 (170 mL) and sat NaCl aq (100 mL) were added and shaken. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. Purification by silica gel column chromatography (eluent; CHCl3 : hexane = 1 : 2) gave 1,3,6,8-tetrakis(triphenylsilylethynyl)pyrene (10, 238 mg, 18% yield). Yellow solid; mp 290°C (dec.); 1H NMR (400 MHz, CDCl3) δ 7.42-7.83 (m, 60H), 8.47 (s, 2H), 8.68 (s, 4H) ppm; 13C NMR(100 MHz, CDCl3) δ 96.9, 106.9, 118.4, 123.5, 127.5, 128.1, 130.1, 132.7, 133.2, 135.0, 135.6 ppm; 29Si NMR (100 MHz, CDCl3) δ -28.5 ppm; IR (KBr) 2147, 3047 cm-1; MS (FAB) m/z (relative intensity, %) 73 (42), 154 (100), 207 (31), 259 (24), 391 (10), 661 (13), 1330 (2, M+); HRMS (FAB) calcd for C96H67Si4: 1331.4320, found: 1331.4312.
  • 46
  • [ 870259-02-2 ]
  • (N,N'-dibutylbenzimidazolin-2-ylidene)gold(I) chloride [ No CAS ]
  • C84H94Au4N8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% Stage #1: 1,3,6,8-tetraethynylpyrene With sodium hydroxide In methanol for 4h; Schlenk technique; Reflux; Stage #2: (N,N'-dibutylbenzimidazolin-2-ylidene)gold(I) chloride In methanol Reflux; Schlenk technique;
  • 47
  • [ 870259-02-2 ]
  • C33H42AuClN2 [ No CAS ]
  • C156H174Au4N8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% Stage #1: 1,3,6,8-tetraethynylpyrene With sodium hydroxide In methanol for 4h; Schlenk technique; Reflux; Stage #2: C33H42AuClN2 In methanol Reflux; Schlenk technique;
  • 48
  • [ 870259-02-2 ]
  • [ 14243-64-2 ]
  • C96H66Au4P4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
30% Stage #1: 1,3,6,8-tetraethynylpyrene With sodium hydroxide In methanol for 4h; Schlenk technique; Reflux; Stage #2: (triphenylphosphine)gold(I) chloride In methanol Reflux; Schlenk technique;
  • 49
  • [ 870259-02-2 ]
  • [ 255829-32-4 ]
  • C128H118N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
30% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine In tetrahydrofuran at 70℃; for 16h;
  • 50
  • [ 870259-02-2 ]
  • [ 58047-43-1 ]
  • C104H78N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine In tetrahydrofuran at 70℃; for 16h;
  • 51
  • [ 870259-02-2 ]
  • [ 69591-40-8 ]
  • 1,3,6,8-tetrakis((2,3,5,6,8,9,11,12-octahydrobenzo[b][1,4,7,10,13]pentaoxacyclopentadecin-15-yl)ethynyl)pyrene [ No CAS ]
YieldReaction ConditionsOperation in experiment
7% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine; triphenylphosphine In tetrahydrofuran at 80℃; for 19h; Inert atmosphere;
  • 52
  • [ 870259-02-2 ]
  • C50H61BrN2O4 [ No CAS ]
  • C224H250N8O16 [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In toluene at 80℃; for 72h; Inert atmosphere;
  • 53
  • [ 870259-02-2 ]
  • [ 1080663-37-1 ]
  • hexadecabutyl-1,1′,1′′,1′′′-[pyrene-1,3,6,8-tetrayltetrakis(ethyne-2,1-diyl)]tetrakis(perylene-3,4,9,10-tetracarboxylate) [ No CAS ]
YieldReaction ConditionsOperation in experiment
44.4% Stage #1: tetrabutyl 1-bromoperylene-3,4,9,10-tetracarboxylate With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine at 60℃; for 0.0833333h; Inert atmosphere; Stage #2: 1,3,6,8-tetraethynylpyrene for 24h; Inert atmosphere;
  • 54
  • [ 870259-02-2 ]
  • C44H36NO(1+)*I(1-) [ No CAS ]
  • C196H154N4(4+)*4I(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
47% In dimethyl sulfoxide at 140℃; for 72h; Schlenk technique; Inert atmosphere;
  • 55
  • [ 870259-02-2 ]
  • dineopentyl 4',4'''-(4-oxo-3,5-diphenylcyclopenta-2,5-diene-1,2-diyl)bis-([1,1'-biphenyl]-4-sulfonate) [ No CAS ]
  • C184H122O24S8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% Stage #1: 1,3,6,8-tetraethynylpyrene; dineopentyl 4',4'''-(4-oxo-3,5-diphenylcyclopenta-2,5-diene-1,2-diyl)bis-([1,1'-biphenyl]-4-sulfonate) In o-xylene at 145℃; for 36h; Inert atmosphere; Sealed tube; Microwave irradiation; Stage #2: In N,N-dimethyl-formamide at 180℃; for 48h; Inert atmosphere; Microbiological reaction; Sealed tube;
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