Effects of mono-substituents on the polarity-sensitive fluorescent probe properties of pyrene
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Updated: May 21, 2025

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
Haiyan Wang1, Jing Zhang2, Yong Zhang3
1State Key Laboratory of Marine Environmental Sciences of China (Xiamen University), College of Environment and Ecology, Xiamen University, Xiamen 361102, PR China; Key Laboratory of Estuarine Ecological Security and Environmental Health (Fujian Province University), Xiamen University Tan Kah Kee College, Zhangzhou 363105, PR China.
Abstract:
This study investigates the effects of mono-substituents (i.e., hydroxyl, methyl, amino and nitro groups) on the polarity-sensitive fluorescent probe properties of pyrene (Pyr) using fluorescence, UV-vis, and circular dichroism absorption spectroscopy. The results indicate that the four mono-substituents altered the fluorescence spectral characteristics of Pyr to varying degrees, with the most to least influential order being: nitro, amino, hydroxyl, and methyl. 1-Aminopyrene (1-APyr) and 1-nitropyrene (1-NPyr) are deemed unsuitable for use as polarity-sensitive fluorescent probes due to their limited or absent spectral characteristics. The I386/I406 and I376/I396 ratios of 1-HPyr and 1-MPyr decrease as solvents polarity increases, contrasting with the I372/I384 ratio of Pyr. Thus, 1-hydroxypyrene (1-HPyr) and 1-methylpyrene (1-MPyr) also exhibit polarity-sensitive characteristics similar to Pyr, and their solubility in PBS buffer surpasses that of Pyr at 298 K. Moreover, 1-HPyr and 1-MPyr are practicable for detecting the polarity of human serum albumin (HSA) under simulated physiological conditions. The results underscore the potential of the polarity-sensitive mono-substituents of Pyr in biological applications, particularly in probing protein polarity and conformational changes, and further providing a potential tool for the related research in biochemistry and pathology.
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