2-[(5-{4-[bis({4-[5-(2,2-dicyanoeth-1-en-1-yl)thiophen-2-yl]phenyl})amino]phenyl}thiophen-2-yl)methylidene]propanedinitrile

• ChemBase ID: 140478
• Molecular Formular: C42H21N7S3
• Molecular Mass: 719.85804
• Monoisotopic Mass: 719.10205671
• SMILES: c1cc(ccc1c1ccc(s1)C=C(C#N)C#N)N(c1ccc(cc1)c1ccc(s1)C=C(C#N)C#N)c1ccc(cc1)c1ccc(s1)C=C(C#N)C#N
• Canonical SMILES: N#CC(=Cc1ccc(s1)c1ccc(cc1)N(c1ccc(cc1)c1ccc(s1)C=C(C#N)C#N)c1ccc(cc1)c1ccc(s1)C=C(C#N)C#N)C#N
• InChI: 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
• InChIKey: KJHGHQMIPHPKIY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(5-{4-[bis({4-[5-(2,2-dicyanoeth-1-en-1-yl)thiophen-2-yl]phenyl})amino]phenyl}thiophen-2-yl)methylidene]propanedinitrile
• IUPAC Traditional name: 2-[(5-{4-[bis({4-[5-(2,2-dicyanoeth-1-en-1-yl)thiophen-2-yl]phenyl})amino]phenyl}thiophen-2-yl)methylidene]propanedinitrile
• Synonyms: TDCV-TPA; Tris[4-(5-dicyanomethylidenemethyl-2-thienyl)phenyl]amine; 三[4-(5-二氰基亚甲基甲基-2-噻吩基)苯基]胺

Database IDs

• CAS Number: 883236-54-2
• MDL Number: MFCD09836233
• PubChem SID: 162234722
• PubChem CID: 71310445

CALCULATED PROPERTIES

• H Acceptors: 7
• H Donor: 0
• LogD (pH = 5.5): 10.563189
• LogD (pH = 7.4): 10.563189
• Log P: 10.563189
• Molar Refractivity: 207.7535 cm^3
• Polarizability: 80.12681 Å^3
• Polar Surface Area: 145.98 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 400 °C
• Fluorescence: λex 510 nm; λem 592 nm in chloroform
• Orbital energy: HOMO 6 eV; LUMO 4.2 eV

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 97%
• OPV Device Performance: ITO/PEDOT:PSS/TDCV-TPA/Al2• 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/AL2• 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/Al3• 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 %
• Empirical Formula (Hill Notation): C42H21N7S3

DETAILS

Sigma Aldrich - 687251

Packaging
100 mg in glass bottle
Application
Isotropic organic semiconductor for OPV′s and OLED′s. TDCV-TPA1,2 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.