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Updated: Dec 11, 2025

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Solvatochromism and mechanochromism observed in a triphenylamine derivative
Chunyang Guo1, Qi Zhang2, Bingqing Zhu2
1Laboratory of Pharmaceutical Crystal Engineering and Technology, School of Pharmacy and †Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, Shanghai, 200237, People's Republic of China.
Abstract:
A donor-π-acceptor fluorescent dye, 4-[N,N-di(4-phenyl)amino]benzaldehyde 4-chlorobenzoyl hydrazone (TPA-CBH), based on a triphenylamine derivative (TPA) and 4-chlorobenzoyl hydrazine (CBH) was designed and synthesized. The optical properties of this luminogen were investigated in solutions as well as in the solid states. In the intramolecular charge-transfer (CT) mechanism, TPA-CBH exhibits solvatochromism when dissolved in various polar solvents. Aggregation-induced emission was observed with the changes of tetrahydrofuran/water ratios. In the solid state, mechanochromic fluorescence is observed when the samples are stressed under different conditions. Based on structural analyses and theoretical calculations, it is found that intra- and intermolecular CT processes play a key role in the diversity of fluorescent properties.
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