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Electronically‐tuned 2‐(2′‐Hydroxyphenyl)‐4‐pyrenylthiazole through Bond Energy Transfer Donor–Acceptor Couples: Sensing and Biological Applications
Author(s) -
Huh Joon Hyuk,
Pandith Anup,
Cho Chan Sik,
Kim HongSeok
Publication year - 2018
Publication title -
bulletin of the korean chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.237
H-Index - 59
ISSN - 1229-5949
DOI - 10.1002/bkcs.11617
Subject(s) - pyrene , chemistry , photochemistry , quenching (fluorescence) , hydrogen bond , acceptor , intermolecular force , molecule , excited state , conjugated system , fluorescence , organic chemistry , polymer , physics , quantum mechanics , nuclear physics , condensed matter physics
A novel pyrene‐conjugated 2‐(2′‐hydroxyphenyl)thiazole probe (HPTP, 1 ) was prepared, and its photophysical and sensing properties were investigated and compared to those of four model compounds. HPTP effectively detects CN − and glycerol in DMSO, with “ turn off” at 425 nm and “ turn on” at 495 nm. The sensing ability of 1 towards CN − ions in DMSO, mediated by the hydrogen bonding‐induced disaggregation of aggregates, resulted in the quenching of ESIPT emission at 425 nm. By contrast, in a DMSO–glycerol mixed medium, the aggregate size increased together with the increased degree of intermolecular π–π interactions between two pyrene units located on adjacent molecules, and resulted in partial inhibition of energy/charge transfer from the pyrene unit to the thiazole unit in the excited state. Excitation energy transfer with increased photostability of the ESIPT core was effectively demonstrated in Candida albicans cell lines.