2-[(5Z)-5-({4-[4-(2,2-diphenylethenyl)phenyl]-1H,2H,3H,3aH,4H,8bH-cyclopenta[b]indol-7-yl}methylidene)-2-(3-ethyl-4-oxo-2-sulfanylidene-1,3-thiazolidin-5-ylidene)-4-oxo-1,3-thiazolidin-3-yl]acetic acid

• ChemBase ID: 165334
• Molecular Formular: C42H35N3O4S3
• Molecular Mass: 741.94
• Monoisotopic Mass: 741.17896962
• SMILES: c12c(N(C3C1CCC3)c1ccc(cc1)/C=C(\c1ccccc1)/c1ccccc1)ccc(c2)/C=c\1/c(=O)n(/c(=C\2/C(=O)N(C(=S)S2)CC)/s1)CC(=O)O
• Canonical SMILES: CCN1C(=S)S/C(=c\2/s/c(=C\c3ccc4c(c3)C3CCCC3N4c3ccc(cc3)/C=C(/c3ccccc3)\c3ccccc3)/c(=O)n2CC(=O)O)/C1=O
• InChI: InChI=1S/C42H35N3O4S3/c1-2-43-40(49)38(52-42(43)50)41-44(25-37(46)47)39(48)36(51-41)24-27-18-21-35-33(23-27)31-14-9-15-34(31)45(35)30-19-16-26(17-20-30)22-32(28-10-5-3-6-11-28)29-12-7-4-8-13-29/h3-8,10-13,16-24,31,34H,2,9,14-15,25H2,1H3,(H,46,47)/b36-24-,41-38+
• InChIKey: OZFUEQNYOBIXTB-SJIUXOFISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(5Z)-5-({4-[4-(2,2-diphenylethenyl)phenyl]-1H,2H,3H,3aH,4H,8bH-cyclopenta[b]indol-7-yl}methylidene)-2-(3-ethyl-4-oxo-2-sulfanylidene-1,3-thiazolidin-5-ylidene)-4-oxo-1,3-thiazolidin-3-yl]acetic acid
• IUPAC Traditional name: [(5Z)-5-({4-[4-(2,2-diphenylethenyl)phenyl]-1H,2H,3H,3aH,8bH-cyclopenta[b]indol-7-yl}methylidene)-2-(3-ethyl-4-oxo-2-sulfanylidene-1,3-thiazolidin-5-ylidene)-4-oxo-1,3-thiazolidin-3-yl]acetic acid
• Synonyms: 5-[[4-[4-(2,2-Diphenylethenyl)phenyl]-1,2,3,3a,4,8b-hexahydrocyclopent[b]indol-7-yl]methylene]-2-(3-ethyl-4-oxo-2-thioxo-5-thiazolidinylidene)-4-oxo-3-thiazolidineacetic Acid; D-149 Dye

Database IDs

• CAS Number: 786643-20-7
• PubChem SID: 162259467
• PubChem CID: 58239565

CALCULATED PROPERTIES

• Acid pKa: 3.5655348
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 7.364708
• LogD (pH = 7.4): 5.939741
• Log P: 9.295117
• Molar Refractivity: 235.7876 cm^3
• Polarizability: 82.46836 Å^3
• Polar Surface Area: 81.16 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D100020

Organic dye for highly efficient solid-state dye-sensitized solar cells.

REFERENCES

• O'Regan, B., et al.: Nature, 353, 737 (1991)
• Kruger, J., et al.: Appl. Phys. Lett., 81, 367 (1991)
• Sayama, K., et al.: Sol. Energy Mater Sol. Cells., 80, 47 (1991)