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.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
