Excited-state intramolecular proton transfer (ESIPT) fine tuned by quinoline-pyrazole isomerism : π-conjugation effect on ESIPT

Research output: Journal Publications and Reviews (RGC: 21, 22, 62)21_Publication in refereed journalpeer-review

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Author(s)

  • Min-Wen Chung
  • Tsung-Yi Lin
  • Cheng-Chih Hsieh
  • Kuo-Chun Tang
  • Hungshin Fu
  • Pi-Tai Chou
  • Shen-Han Yang

Detail(s)

Original languageEnglish
Pages (from-to)7886-7891
Journal / PublicationJournal of Physical Chemistry A
Volume114
Issue number30
Online published14 Jul 2010
Publication statusPublished - 5 Aug 2010
Externally publishedYes

Abstract

A series of quinoline/isoquinoline-pyrazole isomers (I-III), in which the pyrazole moiety is in a different substitution position, was strategically designed and synthesized, showing a system with five-membered intramolecular hydrogen bonding. Despite the similarity in molecular structure, however, only I undergoes excited-state intramolecular proton transfer, as evidenced by the distinct 560 nm proton-transfer emission and its associated relaxation dynamics. The experimental results support a recent theoretical approach regarding the conjugation effect on a proton (or hydrogen atom) transfer reaction (J. Phys. Chem. A 2009, 113, 4862-4867). The concept simply predicts that more extended π conjugation, i.e., resonance, for proton-transfer tautomer species could allow for efficient delocalization of excess charge in the reaction center, resulting in a larger thermodynamic driving force for proton transfer. © 2010 American Chemical Society.

Citation Format(s)

Excited-state intramolecular proton transfer (ESIPT) fine tuned by quinoline-pyrazole isomerism : π-conjugation effect on ESIPT. / Chung, Min-Wen; Lin, Tsung-Yi; Hsieh, Cheng-Chih et al.

In: Journal of Physical Chemistry A, Vol. 114, No. 30, 05.08.2010, p. 7886-7891.

Research output: Journal Publications and Reviews (RGC: 21, 22, 62)21_Publication in refereed journalpeer-review