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Diaryldistyrylpyrazines: Solvatochromic and Acidochromic Fluorophores
Author(s) -
Schmitt Volker,
Moschel Sebastian,
Detert Heiner
Publication year - 2013
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/ejoc.201300463
Subject(s) - solvatochromism , chemistry , pyrazine , substituent , protonation , photochemistry , fluorescence , absorption (acoustics) , quenching (fluorescence) , polarity (international relations) , solvent polarity , stereochemistry , molecule , organic chemistry , solvent , ion , biochemistry , physics , cell , quantum mechanics , acoustics
Abstract Diaryldimethylpyrazines are the starting materials for the synthesis of C 2 ‐symmetric donor‐ or acceptor‐substituted distyrylpyrazines. The optical properties of these cruciform‐shaped dyes are dominated by the distyrylpyrazine units; the photophysics is controlled by the styryl substitution, the diaryl substituents on the central pyrazine only having a small effect. Protonation occurs on the pyrazine and/or lateral amines or azines, thereby altering the absorption and emission properties. Hypso‐ and bathochromism as well as fluorescence quenching depend on the nature of the terminal substituent. This, and a significant positive solvatochromism of the fluorescence, allow optical sensing of the pH and polarity of the environment.