New regioisomeric naphthol-substituted thiazole based ratiometric fluorescence sensor for Zn2+ with a remarkable red shift in emission spectra

Aasif Helal; Mohammad Harun Or Rashid; Cheol Ho Choi; Hong Seok Kim

doi:10.1016/j.tet.2011.10.106

New regioisomeric naphthol-substituted thiazole based ratiometric fluorescence sensor for Zn²⁺ with a remarkable red shift in emission spectra

Aasif Helal
, Mohammad Harun Or Rashid
, Cheol Ho Choi
, Hong Seok Kim^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

58 Scopus citations

Abstract

Ratiometric fluorescent chemosensors based on the position of ring annulation of the naphthol-thiazole moiety for quantification of zinc ions in aqueous ethanol were synthesized and investigated. It was found that sensor 3 exhibited a remarkably large red shift of 140 nm in emission upon complexation with Zn²⁺. A TD-B3LYP/6-31G (d,p) calculation was performed to characterize the nature of the fluorescence behavior of sensor 3 upon Zn ²⁺ complexation. The combination of experimental and computational analyses provides a more complete understanding of the molecular level origin of these unique photophysical properties of this type of chemosensor.

Original language	English
Pages (from-to)	647-653
Number of pages	7
Journal	Tetrahedron
Volume	68
Issue number	2
DOIs	https://doi.org/10.1016/j.tet.2011.10.106
State	Published - 14 Jan 2012
Externally published	Yes

Bibliographical note

Funding Information:
This research was supported by the NRF grant funded by MEST in Korea ( NRF-2010-0010070 ). The Research Institute of Industrial Technology at Kyungpook National University also supported A.H.

Keywords

Naphthol-thiazole
Ratiometric fluorescence
Ring annulation
Zinc ion

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tet.2011.10.106

Cite this

@article{9e9ffe48ea264fe88e809fd9b47c9aaf,

title = "New regioisomeric naphthol-substituted thiazole based ratiometric fluorescence sensor for Zn2+ with a remarkable red shift in emission spectra",

abstract = "Ratiometric fluorescent chemosensors based on the position of ring annulation of the naphthol-thiazole moiety for quantification of zinc ions in aqueous ethanol were synthesized and investigated. It was found that sensor 3 exhibited a remarkably large red shift of 140 nm in emission upon complexation with Zn2+. A TD-B3LYP/6-31G (d,p) calculation was performed to characterize the nature of the fluorescence behavior of sensor 3 upon Zn 2+ complexation. The combination of experimental and computational analyses provides a more complete understanding of the molecular level origin of these unique photophysical properties of this type of chemosensor.",

keywords = "Naphthol-thiazole, Ratiometric fluorescence, Ring annulation, Zinc ion",

author = "Aasif Helal and Rashid, \{Mohammad Harun Or\} and Choi, \{Cheol Ho\} and Kim, \{Hong Seok\}",

note = "Funding Information: This research was supported by the NRF grant funded by MEST in Korea ( NRF-2010-0010070 ). The Research Institute of Industrial Technology at Kyungpook National University also supported A.H. ",

year = "2012",

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doi = "10.1016/j.tet.2011.10.106",

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T1 - New regioisomeric naphthol-substituted thiazole based ratiometric fluorescence sensor for Zn2+ with a remarkable red shift in emission spectra

AU - Helal, Aasif

AU - Rashid, Mohammad Harun Or

AU - Choi, Cheol Ho

AU - Kim, Hong Seok

N1 - Funding Information: This research was supported by the NRF grant funded by MEST in Korea ( NRF-2010-0010070 ). The Research Institute of Industrial Technology at Kyungpook National University also supported A.H.

PY - 2012/1/14

Y1 - 2012/1/14

N2 - Ratiometric fluorescent chemosensors based on the position of ring annulation of the naphthol-thiazole moiety for quantification of zinc ions in aqueous ethanol were synthesized and investigated. It was found that sensor 3 exhibited a remarkably large red shift of 140 nm in emission upon complexation with Zn2+. A TD-B3LYP/6-31G (d,p) calculation was performed to characterize the nature of the fluorescence behavior of sensor 3 upon Zn 2+ complexation. The combination of experimental and computational analyses provides a more complete understanding of the molecular level origin of these unique photophysical properties of this type of chemosensor.

AB - Ratiometric fluorescent chemosensors based on the position of ring annulation of the naphthol-thiazole moiety for quantification of zinc ions in aqueous ethanol were synthesized and investigated. It was found that sensor 3 exhibited a remarkably large red shift of 140 nm in emission upon complexation with Zn2+. A TD-B3LYP/6-31G (d,p) calculation was performed to characterize the nature of the fluorescence behavior of sensor 3 upon Zn 2+ complexation. The combination of experimental and computational analyses provides a more complete understanding of the molecular level origin of these unique photophysical properties of this type of chemosensor.

KW - Naphthol-thiazole

KW - Ratiometric fluorescence

KW - Ring annulation

KW - Zinc ion

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DO - 10.1016/j.tet.2011.10.106

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