This synthesis study demonstrates unique solvatochromic properties in azapyrenes, indicating potential applications.
A series of azapyrenes with pyridinium-phenolate-type zwitterionic skeletons was synthesized, and their absorption and solvatochromic properties were investigated. The compound with a neutral quinoid resonance structure exhibited a low-energy band at a shorter wavelength and showed the highest sensitivity to solvent polarity compared with those exhibited by compounds lacking such a resonance structure. Density functional theory calculations suggested that the frontier orbital energy levels and their distributions depend on the positions of the nitrogen atoms and deprotonated hydroxy groups.
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Nishihata et al. (2026) studied this question.
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