Diaryldistyrylpyrazines: Solvatochromic and Acidochromic Fluorophores

作者：Schmitt Volker; Moschel Sebastian; Detert Heiner^*

来源：European Journal of Organic Chemistry, 2013, 2013(25): 5655-5669.

DOI：10.1002/ejoc.201300463

• Solvatochromism
• Acidochromism
• Fluorescence
• Nitrogen heterocycles
• Conjugation

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.

• 出版日期2013-9