Journal
JOURNAL OF PHYSICAL ORGANIC CHEMISTRY
Volume 18, Issue 9, Pages 962-973Publisher
WILEY
DOI: 10.1002/poc.935
Keywords
cis/trans isomers; 2,5-diphenyl-1,4-distyrylbenzene; luminescence; oligomeric phenylenvinylene; theoretical calculation; Wittig reactions
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2,5-Diphenyl-1,4-distyrylbenzene (DPDSB) with all-cis (cis-DPDSB) and all-trans double bonds (trans-DPDSB) were synthesized by Wittig reaction and the differences in structural and optical properties between the cis-and trans-isomers are discussed in detail. Both compounds were fully characterized by NMR spectroscopy, FT-IR spectroscopy, x-ray crystallography, differential scanning calorimetry (DSC) and electrochemical methods. X-ray analysis and molecular simulation revealed that the structure of cis-DPDSB obviously deviates from planarity along both the distyrylbenzene and terphenyl directions, and less intermolecular interaction exists in crystal. The cisisomer shows a large blue shift in the absorption spectrum in comparison with that of the trans-isomer, and cyclic voltammetric measurements give bandgaps of 3.16 and 2.97 eV for cis- and trans-DPDSB, respectively. Both compounds show unusually strong blue fluorescence in the solid state, probably due to the weak intermolecular interaction existing in both isomers owing to the large steric hindrance induced by the substituted phenyl groups. DSC experiments determined that both isomers have excellent thermal stability, which indicates that they can be used as active layers to make stable devices. Quantum chemical calculations for the frontier molecular orbital and the cation and anion properties reveal that the HOMO and LUMO are completely localized in the distyrylbenzene direction and the distyrylbenzene segment has more sensitive electroactivity than the terphenyl segment whether it is cis- or trans-DPDSB. Copyright (c) 2005 John Wiley & Sons.
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