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Synthesis, Structure and Solvatochromism of the Emission of Cyano‐Substituted Oligo(phenylenevinylene)s
Author(s) -
Detert Heiner,
Schollmeyer Dieter,
Sugiono Erli
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200108)2001:15<2927::aid-ejoc2927>3.0.co;2-v
Subject(s) - chemistry , solvatochromism , benzonitrile , oligomer , photochemistry , fluorescence , nitrile , molecule , knoevenagel condensation , nucleophilic aromatic substitution , polymer chemistry , polar effect , nucleophilic substitution , organic chemistry , physics , quantum mechanics , catalysis
Strongly luminescent and highly soluble oligo(phenylenevinylene)s with five benzene rings and cyano groups in different positions of the terminal styrene units were prepared by means of Horner and Knoevenagel reactions. The substitution pattern − cyanide moieties on the vinyl or on the aromatic regions, together with the effect of auxochromic groups − has distinct influences on the electronic spectra, particularly on the fluorescence. Polar solvents induce red shifts and strongly reduce the fluorescence intensity of the vinyl‐substituted oligomers. Cyano substitution increases the electron affinity of the oligomers; this effect is more pronounced for molecules with vinyl cyanides and can be altered by the presence of additional electron‐donating or electron‐withdrawing groups. The molecular structures of one oligomer bearing cyano groups on the vinylene segments and one with benzonitrile units have been resolved.