Tailoring the excited-state intramolecular proton transfer (ESIPT) fluorescence of 2-(2′-hydroxyphenyl)benzoxazole derivatives

Jangwon Seo, Sehoon Kim, Sanghyuk Park, Young Park Soo

Research output: Contribution to journalArticle

41 Citations (Scopus)

Abstract

The excited-state intramolecular proton transfer (ESIPT) fluorescence in the 2-(2′-hydroxyphenyl)benzoxazole (HBO) derivatives with different electron donor and acceptor substituents was studied by spectroscopic and theoretical methods. Changes in the electronic transition, energy levels, and orbital diagrams of HBO analogues were investigated by the semi-empirical molecular orbital calculation and were correlated with the experimental spectral position of ESIPT keto emission. It was found that the presence of substituents, regardless of their nature, resulted in the red-shifted absorption relative to HBO. However, the spectral change of the ESIPT fluorescence was differently affected by the nature of substituent: hypsochromic shift with electron donor and bathochromic shift with electron acceptor.

Original languageEnglish
Pages (from-to)1706-1710
Number of pages5
JournalBulletin of the Korean Chemical Society
Volume26
Issue number11
DOIs
Publication statusPublished - 2005 Nov 20
Externally publishedYes

Fingerprint

Benzoxazoles
Proton transfer
Excited states
Fluorescence
Derivatives
Electrons
Orbital calculations
Molecular orbitals
Electron transitions
Electron energy levels

Keywords

  • 2-(2′- Hydroxyphenyl)benzoxazole (HBO)
  • ESIPT fluorescence
  • Excited-state intramolecular proton transfer (ESIPT)
  • Substituent effect

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Tailoring the excited-state intramolecular proton transfer (ESIPT) fluorescence of 2-(2′-hydroxyphenyl)benzoxazole derivatives. / Seo, Jangwon; Kim, Sehoon; Park, Sanghyuk; Soo, Young Park.

In: Bulletin of the Korean Chemical Society, Vol. 26, No. 11, 20.11.2005, p. 1706-1710.

Research output: Contribution to journalArticle

@article{033afbd1dfb843beb2db51e36902e0be,
title = "Tailoring the excited-state intramolecular proton transfer (ESIPT) fluorescence of 2-(2′-hydroxyphenyl)benzoxazole derivatives",
abstract = "The excited-state intramolecular proton transfer (ESIPT) fluorescence in the 2-(2′-hydroxyphenyl)benzoxazole (HBO) derivatives with different electron donor and acceptor substituents was studied by spectroscopic and theoretical methods. Changes in the electronic transition, energy levels, and orbital diagrams of HBO analogues were investigated by the semi-empirical molecular orbital calculation and were correlated with the experimental spectral position of ESIPT keto emission. It was found that the presence of substituents, regardless of their nature, resulted in the red-shifted absorption relative to HBO. However, the spectral change of the ESIPT fluorescence was differently affected by the nature of substituent: hypsochromic shift with electron donor and bathochromic shift with electron acceptor.",
keywords = "2-(2′- Hydroxyphenyl)benzoxazole (HBO), ESIPT fluorescence, Excited-state intramolecular proton transfer (ESIPT), Substituent effect",
author = "Jangwon Seo and Sehoon Kim and Sanghyuk Park and Soo, {Young Park}",
year = "2005",
month = "11",
day = "20",
doi = "10.5012/bkcs.2005.26.11.1706",
language = "English",
volume = "26",
pages = "1706--1710",
journal = "Bulletin of the Korean Chemical Society",
issn = "0253-2964",
publisher = "Wiley-Blackwell",
number = "11",

}

TY - JOUR

T1 - Tailoring the excited-state intramolecular proton transfer (ESIPT) fluorescence of 2-(2′-hydroxyphenyl)benzoxazole derivatives

AU - Seo, Jangwon

AU - Kim, Sehoon

AU - Park, Sanghyuk

AU - Soo, Young Park

PY - 2005/11/20

Y1 - 2005/11/20

N2 - The excited-state intramolecular proton transfer (ESIPT) fluorescence in the 2-(2′-hydroxyphenyl)benzoxazole (HBO) derivatives with different electron donor and acceptor substituents was studied by spectroscopic and theoretical methods. Changes in the electronic transition, energy levels, and orbital diagrams of HBO analogues were investigated by the semi-empirical molecular orbital calculation and were correlated with the experimental spectral position of ESIPT keto emission. It was found that the presence of substituents, regardless of their nature, resulted in the red-shifted absorption relative to HBO. However, the spectral change of the ESIPT fluorescence was differently affected by the nature of substituent: hypsochromic shift with electron donor and bathochromic shift with electron acceptor.

AB - The excited-state intramolecular proton transfer (ESIPT) fluorescence in the 2-(2′-hydroxyphenyl)benzoxazole (HBO) derivatives with different electron donor and acceptor substituents was studied by spectroscopic and theoretical methods. Changes in the electronic transition, energy levels, and orbital diagrams of HBO analogues were investigated by the semi-empirical molecular orbital calculation and were correlated with the experimental spectral position of ESIPT keto emission. It was found that the presence of substituents, regardless of their nature, resulted in the red-shifted absorption relative to HBO. However, the spectral change of the ESIPT fluorescence was differently affected by the nature of substituent: hypsochromic shift with electron donor and bathochromic shift with electron acceptor.

KW - 2-(2′- Hydroxyphenyl)benzoxazole (HBO)

KW - ESIPT fluorescence

KW - Excited-state intramolecular proton transfer (ESIPT)

KW - Substituent effect

UR - http://www.scopus.com/inward/record.url?scp=31744446755&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=31744446755&partnerID=8YFLogxK

U2 - 10.5012/bkcs.2005.26.11.1706

DO - 10.5012/bkcs.2005.26.11.1706

M3 - Article

VL - 26

SP - 1706

EP - 1710

JO - Bulletin of the Korean Chemical Society

JF - Bulletin of the Korean Chemical Society

SN - 0253-2964

IS - 11

ER -