Proton-induced fluorescent switching of a new 2D-pi-A type vinylcyanoacetate-pyran dye
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Updated: Jun 26, 2026

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
1Department of Textile System Engineering, Kyungpook National University, Daegu 702-701, Republic of Korea.
Abstract:
A new 2D-pi-A type vinylcyanoacetate-pyran dye, ethyl 2-(2,6-bis(2-butoxy-4-(diethylamino)styryl)-4H-pyran-4-ylidene)-2-cyanoacetate (BDPC) was prepared by condensation reaction. The chemical structures of all the intermediates and the BDPC dye are characterized by (1)H NMR, MS. It showed interestingly solvatochromic and solvatofluorchromic properties in various solvents. Its LUMO and HOMO values were obtained by the theoretical calculation. The fluorescent intensity of BDPC dye can be reversibly selected by protonation/deprotonation of the amine moiety via control of intramolecular charge transfer (ICT), leading to a fluorescent molecular switch with two distinguished "on" and "off" states.
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