| Summary: | Thiophene ring-enhancing electron delocalization imparts unique properties to azoic chromophore tools. The novel TA-OH dye contains a push–pull π-electron system, including a thiophene-azo scaffold with a hydroxyl group at the <i>ortho</i> position to the azo bridge. The hydroxyl group is expected to lock the azo bridge in its <i>trans</i> conformation, concurring with the photostability and fastness of the dye. The single crystal analysis identified the molecule’s primary conjugation plane, and the theoretical analysis provided electronic pattern insights. The absorption behavior and the <i>trans</i>-to-<i>cis</i> conversion were examined from both experimental and theoretical perspectives. The effect of solvent polarity and the role of pH on the photophysical properties were explored. The solvent polarity strongly affects the absorbance spectrum of TA-OH, therefore potentially making NLO active. Additionally, TA-OH exhibited pH responsiveness akin to classic dichromatic pH indicators, with a noticeable color shift from red to blue observed as pH transitioned from neutral to alkaline. Absorbance titration experiments, along with experimental/theoretical determination of pKa, defined the pH sensing ability.
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