Competitive intramolecular hydrogen bonding formation and excited-state proton transfer reaction in 1-[(diethylamino)-methyl]-2-hydroxy-3-naphthaldehyde

Autor:	Ya-Hui Hu, Yu-Shan Lin, Jen-Kan Yu, Shih-Chieh Pu, Pi-Tai Che, Kun-Chan Wu, Yi-Ming Cheng, Yu-Shan Yeh
Rok vydání:	2004
Předmět:	Hydrogen Hydrogen bond General Physics and Astronomy chemistry.chemical_element Chromophore Photochemistry chemistry.chemical_compound Delocalized electron chemistry Intramolecular force Zwitterion Excited state Physical and Theoretical Chemistry Conformational isomerism
Zdroj:	Chemical Physics Letters. 384:203-209
ISSN:	0009-2614
DOI:	10.1016/j.cplett.2003.11.058
Popis:	1-[(diethylamino)-methyl]-2-Hydroxy-3-naphthaldehyde (DMHN) possessing dual hydrogen bonding (HB) sites (O–H⋯NR2 (conformer A) and O–H⋯OC (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 (λmax∼485 nm) and an extremely weak keto-tautomer (λmax∼730 nm) emission, respectively. The response-limited rise dynamics for both A and B conformers (
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::40f33db29e493bb31b310b9a3a4b619a https://doi.org/10.1016/j.cplett.2003.11.058 Zobrazit plný text záznamu Full Text from ScienceDirect