Abstract
The fluorescence behavior of firefly luciferin analogues 2-(4-(6-hydroxybenzo[d]thiazol-2-yl)phenyl)-4,5-dihydrothiazole-4-carboxylicacid (DHC) has been theoretically studied. DHC and water molecules undergo intermolecular proton transfer (PT) and form the anion configuration in the excited state. The fluorescence of this anion form (603 nm) is consistent with the experimental result (595 nm). The hydroxyl substitution DHC-OH forms an intramolecular hydrogen bond O1–H1•••N2 that hinders the intermolecular PT and induces the intramolecular PT. The fluorescence peak of DHC-OH-PT at 528 nm was consistent with the experimental results (518 nm), which confirmed that DHC-OH mainly undergoes intramolecular PT.
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