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[ CAS No. 3978-81-2 ] {[proInfo.proName]}

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Ravinder Kaur ; Niharika Dalpati ; Jared H. Delcamp , et al. DOI:

Abstract: Dye-sensitized solar cells (DSCs) are important to indoor solar powered devices and energy sustainable buildings because of their remarkable performance under indoor/ambient light conditions. Triiodide/iodide (I3–/I–) has been used as the most common redox mediator in DSCs because of its desirable kinetic properties and multielectron redox cycle. However, the low redox potential, corrosiveness, competitive visible light absorption, and lack of tunability of this redox mediator limit its performance in many DSC devices. Here we report a class of complex redox shuttles which operate on a similar multielectron redox cycle as I3–/I– while maintaining desirable kinetics and improving on its limitations. These complexes, dithiocarbamates, were evaluated as redox shuttles in DSCs, which exhibited excellent performance under low light conditions. The recombination behavior of the redox shuttles with electrons in TiO2, dye regeneration behavior, and counter electrode electron transfer resistance were studied via chronoamperometry and electrochemical impedance spectroscopy (EIS). Further, DSC devices were studied with the Ni-based redox shuttles via incident photon-to-current conversion efficiencies (IPCEs) and current–voltage (J–V) curves under varied light intensities. The Ni-based redox shuttles showed up to 20.4% power conversion efficiency under fluorescent illumination, which was higher than I3–/I–-based devices (13%) at similar electrolyte concentrations. Taken together, these results show that dithiocarbamate redox shuttles have faster rates of dye regeneration than the I3–/I– shuttle but suffer from faster recombination of photoinjected electrons with oxidized Ni(IV) species, which decrease photovoltages.

Keywords: dye-sensitized solar cells ; nickel(IV) ; redox shuttle ; dithiocarbamate ; indoor photovoltaic

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Product Details of [ 3978-81-2 ]

CAS No. :3978-81-2 MDL No. :MFCD00006435
Formula : C9H13N Boiling Point : -
Linear Structure Formula :- InChI Key :YSHMQTRICHYLGF-UHFFFAOYSA-N
M.W : 135.21 Pubchem ID :19878
Synonyms :

Calculated chemistry of [ 3978-81-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.44
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 43.51
TPSA : 12.89 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.33 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.02
Log Po/w (XLOGP3) : 2.53
Log Po/w (WLOGP) : 2.38
Log Po/w (MLOGP) : 1.8
Log Po/w (SILICOS-IT) : 2.46
Consensus Log Po/w : 2.24

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.65
Solubility : 0.303 mg/ml ; 0.00224 mol/l
Class : Soluble
Log S (Ali) : -2.45
Solubility : 0.483 mg/ml ; 0.00357 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.2
Solubility : 0.0847 mg/ml ; 0.000627 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.0

Safety of [ 3978-81-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 3978-81-2 ]

* 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.

  • Upstream synthesis route of [ 3978-81-2 ]
  • Downstream synthetic route of [ 3978-81-2 ]

[ 3978-81-2 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 38442-51-2 ]
  • [ 22581-65-3 ]
  • [ 3978-81-2 ]
  • [ 5944-41-2 ]
  • [ 29939-31-9 ]
Reference: [1] Journal of Organic Chemistry, 1995, vol. 60, # 17, p. 5390 - 5395
  • 2
  • [ 110-86-1 ]
  • [ 89379-02-2 ]
  • [ 3978-81-2 ]
  • [ 5944-41-2 ]
Reference: [1] Journal of the American Chemical Society, 1993, vol. 115, # 23, p. 10596 - 10604
  • 3
  • [ 110-86-1 ]
  • [ 38442-51-2 ]
  • [ 3978-81-2 ]
  • [ 5944-41-2 ]
Reference: [1] Journal of Organic Chemistry, 1985, vol. 50, # 18, p. 3423 - 3425
  • 4
  • [ 3978-81-2 ]
  • [ 72914-19-3 ]
YieldReaction ConditionsOperation in experiment
80% With sodium In tetrahydrofuran; paraffin oil at 50℃; for 6 h; In this example, following Example 1, the synthesis of 4,4′-di-tert-butyl-2,2′-bipyridine was investigated. In this example, the synthesis was performed through the reaction of 4-tert-butylpyridine with SD at low concentrations in THF. 4-tert-Butylpyridine (0.5 mmol) was reacted with SD in an amount of molar equivalents with respect to 4-tert-butylpyridine as shown in FIG. 2 in THF. The usage amounts of THF, the reaction temperatures and the reaction times were set as shown in FIG. 2, and the synthesis was performed in the same manner as in Example 1. After the reaction, in the same manner as in Example 1, the production amounts of 4,4′-di-tert-butyl2,2′-bipyridine (Compound 2), which was the target reaction product, and 4-tert-butyl-1,4-dihydropyridine (Compound 1) and 4,4′,4″-tri-tert-butyl-2,2′:6′,2″-terpyridine (Compound 3), which were the possible reaction by-products, were measured, and their yields were calculated. The recovery rate of the unreacted 4-tert-butylpyridine was calculated in the same manner. The results are summarized in FIG. 2. It is found from these results that when 4-tert-butylpyridine (0.5 mmol) was reacted with SD in an amount of 1 to 2 mol equivalents with respect to the 4-tert-butylpyridine in 2 to 4 ml of THF at 25 to 50° C. for 1 to 24 hours, the 4,4′-di-tert-butyl-2,2′-bipyridine compound was obtained with a high yield in all of the cases. In particular, when 0.5 mmol 4-tert-butylpyridine was reacted with SD in an amount of 1 mol equivalent with respect to the 4-tert-butylpyridine in 2 ml of THF at 50° C. for 1 to 6 hours, the 4,4′-di-tert-butyl-2,2′-bipyridine compound was obtained with a high yield without the generation of reaction by-products. In addition, when 0.5 mmol 4-tert-butylpyridine was reacted with SD in an amount of 1 mol equivalent with respect to the 4-tert-butylpyridine in 4 ml of THF at 25° C. for 6 hours, the 4,4′-di-tert-butyl-2,2′-bipyridine compound was obtained with a high yield without the generation of reaction by-products. It was found that when SD in an amount of 2 mol equivalents was used, the yield decreased compared with the case of 1 mol equivalent, and the material balance also decreased. It was also found from comparison with Example 1 that the lower the concentrations of 4-tert-butylpyridine and SD were with respect to THF, the higher the yield was.
Reference: [1] Patent: US2018/282278, 2018, A1, . Location in patent: Paragraph 0057; 0127-0130
[2] Helvetica Chimica Acta, 1980, vol. 63, # 6, p. 1675 - 1702
[3] Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999), 2000, # 1, p. 63 - 68
[4] Inorganica Chimica Acta, 2011, vol. 365, # 1, p. 127 - 132
[5] Synthesis (Germany), 2013, vol. 45, # 22, p. 3099 - 3102
[6] Organometallics, 2016, vol. 35, # 14, p. 2348 - 2360
[7] Patent: US4177349, 1979, A,
[8] Patent: US4177349, 1979, A,
  • 5
  • [ 3978-81-2 ]
  • [ 72914-19-3 ]
YieldReaction ConditionsOperation in experiment
78% With sodium In tetrahydrofuran; paraffin oil at 25℃; for 24 h; In this example, following Example 1, the synthesis of 4,4′-di-tert-butyl-2,2′-bipyridine was investigated. In this example, the synthesis was performed through the reaction of 4-tert-butylpyridine with SD at low concentrations in THF. 4-tert-Butylpyridine (0.5 mmol) was reacted with SD in an amount of molar equivalents with respect to 4-tert-butylpyridine as shown in FIG. 2 in THF. The usage amounts of THF, the reaction temperatures and the reaction times were set as shown in FIG. 2, and the synthesis was performed in the same manner as in Example 1. After the reaction, in the same manner as in Example 1, the production amounts of 4,4′-di-tert-butyl2,2′-bipyridine (Compound 2), which was the target reaction product, and 4-tert-butyl-1,4-dihydropyridine (Compound 1) and 4,4′,4″-tri-tert-butyl-2,2′:6′,2″-terpyridine (Compound 3), which were the possible reaction by-products, were measured, and their yields were calculated. The recovery rate of the unreacted 4-tert-butylpyridine was calculated in the same manner. The results are summarized in FIG. 2. It is found from these results that when 4-tert-butylpyridine (0.5 mmol) was reacted with SD in an amount of 1 to 2 mol equivalents with respect to the 4-tert-butylpyridine in 2 to 4 ml of THF at 25 to 50° C. for 1 to 24 hours, the 4,4′-di-tert-butyl-2,2′-bipyridine compound was obtained with a high yield in all of the cases. In particular, when 0.5 mmol 4-tert-butylpyridine was reacted with SD in an amount of 1 mol equivalent with respect to the 4-tert-butylpyridine in 2 ml of THF at 50° C. for 1 to 6 hours, the 4,4′-di-tert-butyl-2,2′-bipyridine compound was obtained with a high yield without the generation of reaction by-products. In addition, when 0.5 mmol 4-tert-butylpyridine was reacted with SD in an amount of 1 mol equivalent with respect to the 4-tert-butylpyridine in 4 ml of THF at 25° C. for 6 hours, the 4,4′-di-tert-butyl-2,2′-bipyridine compound was obtained with a high yield without the generation of reaction by-products. It was found that when SD in an amount of 2 mol equivalents was used, the yield decreased compared with the case of 1 mol equivalent, and the material balance also decreased. It was also found from comparison with Example 1 that the lower the concentrations of 4-tert-butylpyridine and SD were with respect to THF, the higher the yield was.
Reference: [1] Patent: US2018/282278, 2018, A1, . Location in patent: Paragraph 0057; 0127-0130
[2] Chemistry - A European Journal, 2018, vol. 24, # 55, p. 14830 - 14835
  • 6
  • [ 3978-81-2 ]
  • [ 50488-34-1 ]
YieldReaction ConditionsOperation in experiment
2.9 g
Stage #1: With n-butyllithium; 2-(N,N-dimethylamino)athanol In n-heptane for 1 h; Inert atmosphere; Cooling with ice
Stage #2: With carbon tetrabromide In hexane at 20℃; for 1 h; Cooling with ice
A solution of 2- (dimethylamino) ethanol (4.79 ml, 47.8 mmol) in heptane (200 ml) was stirred in an ice bath under nitrogen. A solution of butyllithium in hexane (38.2 ml, 96 mmol) was slowly added via syringe and stirred at low temperature for 30 min. 4- (tert-Butyl) pyridine (7.0 ml, 47.8 mmol) was slowly added via syringe and the mixture was stirred at low temperature for 1 hour to give an orange solution. The solution was cooled in an iPrOH / CO2 bath and a cooled solution (ice bath) of perbromomethane (19.02 g, 57.3 mmol) dissolved in heptane (200 ml) was slowly added via cannula. The brown heterogeneous reaction mixture was stirred at low temperature for 1 hour and then allowed to warm to room temperature overnight. The mixture was again cooled in an ice bath and carefully quenched with water. The mixture was extracted twice with ether and the combined organics were washed with brine, dried, vacuum reduced and coated onto celite. The result was then eluted on a 300 g silica column using 10-20percent EtOAc / heptane. The brown fraction with Rf ~ 0.3 (10percent EtOAc / heptane) was collected to give 2.90 g of a brown oil (28percent) containing 2-bromo-4- (tert- butyl) pyridine.
Reference: [1] Tetrahedron Letters, 2010, vol. 51, # 50, p. 6622 - 6625
[2] Journal of Organic Chemistry, 1983, vol. 48, # 22, p. 4156 - 4158
[3] Chemical Communications, 2009, # 41, p. 6270 - 6272
[4] Patent: US2011/230462, 2011, A1,
[5] Patent: US9219237, 2015, B1,
[6] Patent: KR2015/102680, 2015, A, . Location in patent: Paragraph 0173-0175
  • 7
  • [ 3978-81-2 ]
  • [ 81167-60-4 ]
Reference: [1] Patent: WO2012/41476, 2012, A1,
[2] Patent: EP2441755, 2012, A1,
[3] Synthesis (Germany), 2013, vol. 45, # 22, p. 3099 - 3102
[4] Patent: US9219237, 2015, B1,
[5] Angewandte Chemie - International Edition, 2016, vol. 55, # 40, p. 12321 - 12324[6] Angew. Chem., 2016, vol. 128, p. 12509 - 12512,4
[7] Patent: JP2017/39654, 2017, A,
  • 8
  • [ 3978-81-2 ]
  • [ 207739-72-8 ]
Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 39, p. 9910 - 9918
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