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Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach

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Metal-Free Synthesis of Hydroxybenzimidazole-Derived ESIPT-AIE Fluorophore Showing Time-Dependent Emission:

Sakshi Maan¹, Saurajit Ghosh¹, Subhendu Adhikari¹

¹Department of Chemistry, Birla Institute of Technology and Science Pilani, Pilani, Rajasthan, India.

Chemistry, an Asian Journal

|November 19, 2025

Abstract:

Here, we present the design and synthesis of regio-isomeric hydroxybenzimidazole-dicyanophenyl-vinyl (OH-BIDCPV) molecules. Through detailed photophysical studies, we found that the ortho-substituted hydroxybenzimidazole-dicyanophenyl-vinyl (o-OH-BIDCPV) exhibits a strong yellow fluorescence emission at 550 nm, attributed to excited-state intramolecular proton transfer (ESIPT)-coupled aggregation-induced emission enhancement (AIEE) in both solid and solution phases. Interestingly, in solution, the 550 nm emission displays a time-dependent enhancement, a relatively rare phenomenon in small molecules. Furthermore, we have utilized o-OH-BIDCPV to develop an activity-based probe for detecting cellular esterase activity inside MCF-7 breast cancer cells.

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