2-(Benzothiazol-2-yl)pyren-1-ol, a new excited state intramolecular proton transfer-based fluorescent sensor for nitroaromatic compounds

Ying Hu, Joonyoung F. Joung, Ji Eun Jeong, Yerin Jeong, Han Young Woo, Yuanbin She, Sungnam Park, Juyoung Yoon

Research output: Contribution to journalArticle

Abstract

2-(Benzothiazol-2-yl)pyren-1-ol (P3-NS) was developed as a excited-state intramolecular proton transfer (ESIPT)- based sensor for nitroaromatic compounds (NACs). Results of studies of its photophysical and optical properties show that P3-NS exists in various, solvent dependent isomeric forms arising from rotation about the C–C bond connecting the benzothiazole and pyren-1-ol rings and the location of the pyrene-OH proton. The results of density functional theory (DFT) calculations enabled identification of the major structures of P3-NS dissolved in different solvents. Upon electronic excitation in nonpolar or weakly polar solvents, P3-NS undergoes an ESIPT reaction to form a product that only weakly fluoresces. In contrast, P3-NS exists in a strongly fluorescent deprotonated form in highly polar solvents. The results of time-dependent DFT calculations indicate that fluorescence quenching of the product generated by ESIPT reaction of P3-NS is caused by intersystem crossing at a conical intersection between S1 and T2 states. The anionic form of P3-NS, present in highly polar solvents, was shown to be a fluorescence sensor for nitroaromatic compounds (NACs). Fluorescence quenching by NACs occurs by protonation of the anionic form of P3-NS (static quenching) and by photoinduced electron transfer from the anionic form to NACs (dynamic quenching).

LanguageEnglish
Pages298-305
Number of pages8
JournalSensors and Actuators, B: Chemical
Volume280
DOIs
Publication statusPublished - 2019 Feb 1

Fingerprint

Proton transfer
Excited states
Quenching
quenching
protons
sensors
Sensors
excitation
Fluorescence
fluorescence
Density functional theory
density functional theory
Protonation
Pyrene
pyrenes
products
intersections
Protons
electron transfer
Optical properties

Keywords

  • Dynamic quenching
  • ESIPT
  • Nitroaromatic compounds
  • Pyrene
  • Static quenching

ASJC Scopus subject areas

  • Electronic, Optical and Magnetic Materials
  • Instrumentation
  • Condensed Matter Physics
  • Surfaces, Coatings and Films
  • Metals and Alloys
  • Electrical and Electronic Engineering
  • Materials Chemistry

Cite this

2-(Benzothiazol-2-yl)pyren-1-ol, a new excited state intramolecular proton transfer-based fluorescent sensor for nitroaromatic compounds. / Hu, Ying; Joung, Joonyoung F.; Jeong, Ji Eun; Jeong, Yerin; Woo, Han Young; She, Yuanbin; Park, Sungnam; Yoon, Juyoung.

In: Sensors and Actuators, B: Chemical, Vol. 280, 01.02.2019, p. 298-305.

Research output: Contribution to journalArticle

Hu, Ying ; Joung, Joonyoung F. ; Jeong, Ji Eun ; Jeong, Yerin ; Woo, Han Young ; She, Yuanbin ; Park, Sungnam ; Yoon, Juyoung. / 2-(Benzothiazol-2-yl)pyren-1-ol, a new excited state intramolecular proton transfer-based fluorescent sensor for nitroaromatic compounds. In: Sensors and Actuators, B: Chemical. 2019 ; Vol. 280. pp. 298-305.
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