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Merck
CN

687251

Tris[4-(5-dicyanomethylidenemethyl-2-thienyl)phenyl]amine

97%

Synonym(s):

TDCV-TPA

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About This Item

Empirical Formula (Hill Notation):
C42H21N7S3
CAS Number:
883236-54-2
Molecular Weight:
719.86
NACRES:
NA.23
PubChem Substance ID:
329761117
UNSPSC Code:
12352103
MDL number:
MFCD09836233

Key Documents

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OPV device performance

ITO/PEDOT:PSS/TDCV-TPA/Al

  • Short-circuit current density (Jsc): 1.7 mA/cm2
  • Open-circuit voltage (Voc): 0.76 V
  • Fill Factor (FF): 0.27
  • Power Conversion Efficiency (PCE): 0.4 %
, ITO/PEDOT:PSS/TDCV-TPA/C60/LiF/AL
  • Short-circuit current density (Jsc): 4.59 mA/cm2
  • Open-circuit voltage (Voc): 1.15 V
  • Fill Factor (FF): 0.28
  • Power Conversion Efficiency (PCE): 1.85 %
, ITO/PEDOT:PSS/TDCV-TPA/PC61BM/Al
  • Short-circuit current density (Jsc): 3.65 mA/cm2
  • Open-circuit voltage (Voc): 0.96 V
  • Fill Factor (FF): 0.29
  • Power Conversion Efficiency (PCE): 1.02 %

InChI

1S/C42H21N7S3/c43-22-28(23-44)19-37-13-16-40(50-37)31-1-7-34(8-2-31)49(35-9-3-32(4-10-35)41-17-14-38(51-41)20-29(24-45)25-46)36-11-5-33(6-12-36)42-18-15-39(52-42)21-30(26-47)27-48/h1-21H

SMILES string

N#C\C(=C/c1ccc(s1)-c2ccc(cc2)N(c3ccc(cc3)-c4ccc(\C=C(/C#N)C#N)s4)c5ccc(cc5)-c6ccc(\C=C(/C#N)C#N)s6)C#N

InChI key

KJHGHQMIPHPKIY-UHFFFAOYSA-N

assay

97%

form

solid

mp

400 °C

fluorescence

λex 510 nm; λem 592 nm in chloroform

orbital energy

HOMO 6 eV , LUMO 4.2 eV 

Application

Isotropic organic semiconductor for OPV′s and OLED′s. TDCV-TPA is soluble in a large variety of organic solvents and can be used for the fabrication of heterojunction solar cells with high open-circuit voltage (1.15V), efficiency close to 2% and longer ambient condition lifetimes than cells based on poly(alkylthiophenes). The compound absorbs at 509nm (in CH2Cl2 solution) and 538nm as thin film. It can be used as high spectral purity luminophore in LED′s, emitting red light at 658nm.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKBN7515V
03707HH

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Cravino, A.; Leriche, P.; Aleveque, O.; Roncali, J.
Advanced Materials, 18, 3033-3033 (2006)
Sophie Roquet et al.
Journal of the American Chemical Society, 128(10), 3459-3466 (2006-03-09)
Star-shaped molecules based on a triphenylamine core derivatized with various combinations of thienylenevinylene conjugated branches and electron-withdrawing indanedione or dicyanovinyl groups have been synthesized. UV-vis absorption and fluorescence emission data show that the introduction of the electron-acceptor groups induces an

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