Open AccessExcited-State Intramolecular Proton Transfer in Five-Membered Hydrogen-Bonding Systems: 2-Pyridyl Pyrazoles
Author(s) -
Wei-Shan Yu,
ChungChih Cheng,
YiMing Cheng,
PeiChi Wu,
YiHwa Song,
Yün Chi,
PiTai Chou
Publication year - 2003
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/ja035382y
Subject(s) - chemistry , intramolecular force , potential energy surface , hydrogen bond , proton , excited state , molecule , photochemistry , relaxation (psychology) , computational chemistry , stereochemistry , organic chemistry , atomic physics , psychology , social psychology , physics , quantum mechanics
The excited-state intramolecular proton transfer (ESIPT) reaction in five-membered N-H...N hydrogen-bonding systems has been explored through design and syntheses of a series of 5-(2-pyridyl) 1-H-pyrazoles 1a-d. The ESIPT mechanism was confirmed through spectroscopy, relaxation dynamics, and corresponding methylated analogues. The results demonstrate for the first time a unique system among ESIPT molecules, in which ESIPT incorporates an appreciably large energy barrier fine-tuned by the skeletal reorganization. This makes 1a-d systems ideal models for probing the reaction potential energy surface.
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom