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Abstract
1-[(diethylamino)-methyl]-2-Hydroxy-3-naphthaldehyde (DMHN) possessing dual hydrogen bonding (HB) sites (O–H⋯NR 2 (conformer A) and O–H⋯OC (conformer B)) has been synthesized to study the competitive excited-state intramolecular proton transfer (ESIPT) reaction. Despite near degeneracy between conformers A and B, the associated chromophores are significantly different and can be rationalized by different degrees of hydrogen bond-induced π electrons delocalization. ESIPT takes place in both conformers A and B in cyclohexane, resulting in a zwitterion ( λ max∼485 nm) and an extremely weak keto-tautomer ( λ max∼730 nm) emission, respectively. The response-limited rise dynamics for both A and B conformers (<150 fs) leads us to conclude that both ESIPT processes are essentially barrierless and the interconversion between two HB conformers is prohibited in the excited state.
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