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Updated: Jul 9, 2025

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
Synthesis of a new fluorophore: wavelength-tunable bisbenzo[f]isoindolylidenes
Changqing Ye1, Rui Huang1,2, Mong-Feng Chiou1
1State Key Laboratory of Structural Chemistry, Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, Fujian Science & Technology Innovation Laboratory for Optoelectronic Information of China, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences 155 Yangqiao Road West Fuzhou Fujian 350002 P. R. China hlbao@fjirsm.ac.cn.
Abstract:
The creation of new functional molecules is a central task in chemical synthesis. Herein, we report the synthesis of a new type of fluorophore, bisbenzo[f]isoindolylidenes, from easily accessible dipropargyl benzenesulfonamides. Wavelength-tunable fluorophores emitting strong fluorescence of green to red light were obtained in this reaction. Late-stage modifications and incorporation of bioactive molecules into these fluorophores give rise to potential applications in biological studies. Detailed computational and experimental studies were conducted to elucidate the mechanism, and suggest a reaction sequence involving Garratt-Braverman type cyclization, isomerization, fragmentation, dimerization and oxidation.
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