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

Authors
Hu, YingJoung, Joonyoung F.Jeong, Ji-EunJeong, YerinWoo, Han YoungShe, YuanbinPark, SungnamYoon, Juyoung
Issue Date
1-2월-2019
Publisher
ELSEVIER SCIENCE SA
Keywords
Nitroaromatic compounds; ESIPT; Pyrene; Static quenching; Dynamic quenching
Citation
SENSORS AND ACTUATORS B-CHEMICAL, v.280, pp.298 - 305
Indexed
SCIE
SCOPUS
Journal Title
SENSORS AND ACTUATORS B-CHEMICAL
Volume
280
Start Page
298
End Page
305
URI
https://scholar.korea.ac.kr/handle/2021.sw.korea/67682
DOI
10.1016/j.snb.2018.10.043
ISSN
0925-4005
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).
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