Diaryldistyrylpyrazines: Solvatochromic and Acidochromic Fluorophores

Diaryldimethylpyrazines are the starting materials for the synthesis of C2‐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 dia...

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Bibliographic Details
Published in:European journal of organic chemistry 2013-09, Vol.2013 (25), p.5655-5669
Main Authors: Schmitt, Volker, Moschel, Sebastian, Detert, Heiner
Format: Article
Language:English
Subjects:
Acidochromism
Conjugation
Fluorescence
Nitrogen heterocycles
Solvatochromism
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Summary:Diaryldimethylpyrazines are the starting materials for the synthesis of C2‐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. Centrosymmetric diaryldistyrylpyrazines with terminal acceptor and donor groups have been prepared. The electronic spectra are highly sensitive towards changes in the environment: solvatochromism and huge Stokes shifts result from large dipole moments of the C2‐symmetric dyes. Protonation induces multiple alterations of absorption and emission, thus allowing optical sensing of the pH and polarity.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201300463