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Solvent‐dependent fluorescence of donor‐substituted ( E )‐1,2‐bis(stilbenyl‐1,3,4‐oxadiazolyl)ethenes
Author(s) -
Detert Heiner,
Sugiono Erli,
Kruse Gabriele
Publication year - 2002
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.523
Subject(s) - chemistry , solvatochromism , intramolecular force , alkoxy group , photochemistry , molecule , fluorescence , conjugated system , luminescence , aryl , absorption (acoustics) , absorption spectroscopy , solvent , stereochemistry , organic chemistry , polymer , alkyl , physics , optoelectronics , quantum mechanics , acoustics
The Huisgen reaction of aryltetrazoles and fumaryl chloride leads to symmetrically aryl‐substituted 1,2‐bis(1,3,4‐oxadiazolyl)ethenes. Molecules with extended conjugated systems are accessible using stilbenyltetrazoles or higher homologues. The substitution with solubility‐permitting alkoxy side‐chains results in molecules of C 2 h symmetry, consisting of a central electron‐accepting segment and two terminal electron density‐releasing units. The solvatochromism of the absorption spectra is negligible, while in the emission spectra a strong positive solvatochromism connected with a dramatic decrease of the quantum yield is observed, indicating intramolecular charge transfer. The influences of different alkoxy substitution patterns on the luminescence properties are discussed. Copyright © 2002 John Wiley & Sons, Ltd.