N−H‐Type Excited‐State Proton Transfer in Compounds Possessing a Seven‐Membered‐Ring Intramolecular Hydrogen Bond
Journal
Chemistry - A European Journal
Journal Volume
22
Journal Issue
41
Pages
14688-14695
Date Issued
2016
Author(s)
Chen, Y.-A.
Meng, F.-Y.
Hsu, Y.-H.
Hung, C.-H.
Chen, C.-L.
Chung, K.-Y.
Tang, W.-F.
Hung, W.-Y.
Abstract
A series of compounds containing 5-(2-aminobenzylidene)-2,3-dimethyl-3,5-dihydro-4H-imidazol-4-one (o-ABDI) as the core chromophore with a seven-membered-ring N-H-type intramolecular hydrogen bond have been synthesized and characterized. The acidity of the N-H proton and thus the hydrogen-bond strength can be fine-tuned by replacing one of the amino hydrogen atoms by a substituent R, the acidity increasing with increasing electron-withdrawing strength of R, that is, in the order H
Type
journal article