Abstract
In this study, we developed an anthracene-based fluorescence sensor (AMG) for detecting high pH values and water contents in organic solvents. A guanidine group was covalently attached to an anthracene fluorophore as the proton receptor to afford highly polar AMG, with reasonable solubility even in highly basic solution. The fluorescence of AMG increased almost linearly with decreasing pH from 13.0 to 11.0. AMG also exhibited a fluorescence turn-on response to water in various organic solvents such as 1,4-dioxane, DMF, CH3CN, and EtOH. The peak intensity of the fluorescence was nearly proportional to the amount of water. Two linear regression curves were used to quantitatively detect the broad range of water content in each solvent. The pH and water sensing mechanisms were explained by the structural differences between a flexible guanidine in AMG and a rigid resonance-stabilized guanidinium moiety in the protonated AMG (AMGH+).
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