European Journal of Organic Chemistry · 2013 · 60 citations · 61 references
EngineeringCentral PyrazineOrganic ChemistryChemistryChemical DerivativePhosphorescence ImagingAbstract DiaryldimethylpyrazinesAcidochromic FluorophoresPhotophysical PropertyBiophysicsBiochemistryPhotochemistryMechanistic PhotochemistryFluorous SynthesisSupramolecular PhotochemistryDistyrylpyrazine UnitsPhotochromismOptical SensorsNatural SciencesSpectroscopy
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.
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