Investigation of desilylation in the recognition mechanism to fluoride by a 1,8-naphthalimide derivative

Jeeun Woo; Gunwoo Kim; Kevanie Quintero; Michael P. Hanrahan; Hector Palencia; Haishi Cao

doi:10.1039/c4ob01500b

Investigation of desilylation in the recognition mechanism to fluoride by a 1,8-naphthalimide derivative

Jeeun Woo, Gunwoo Kim, Kevanie Quintero, Michael P. Hanrahan, Hector Palencia, Haishi Cao

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

12 Scopus citations

Abstract

A reaction-based chemosensor (AF-1) was designed, synthesized and applied as an optical approach for quantitative measurement of F^- in MeCN. In the presence of F^-, selective fluoride-assisted desilylation instantly gave colorimetric and fluorogenic signals, providing a dual-optical channel for the detection of F^-. ¹H NMR titration was carried out to investigate the desilylation process, revealing F^- triggered rapid cleavage of Si-O bond in trimethylsilyl ether. AF-1 exhibited high sensitivity and selectivity to F^- over other anions. The detection limit to F^- was calculated to be 0.05 ppm.

Original language	English (US)
Pages (from-to)	8275-8279
Number of pages	5
Journal	Organic and Biomolecular Chemistry
Volume	12
Issue number	41
DOIs	https://doi.org/10.1039/c4ob01500b
State	Published - Nov 7 2014
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "A reaction-based chemosensor (AF-1) was designed, synthesized and applied as an optical approach for quantitative measurement of F- in MeCN. In the presence of F-, selective fluoride-assisted desilylation instantly gave colorimetric and fluorogenic signals, providing a dual-optical channel for the detection of F-. 1H NMR titration was carried out to investigate the desilylation process, revealing F- triggered rapid cleavage of Si-O bond in trimethylsilyl ether. AF-1 exhibited high sensitivity and selectivity to F- over other anions. The detection limit to F- was calculated to be 0.05 ppm.",

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AU - Woo, Jeeun

AU - Kim, Gunwoo

AU - Quintero, Kevanie

AU - Hanrahan, Michael P.

AU - Palencia, Hector

AU - Cao, Haishi

N1 - Publisher Copyright: © the Partner Organisations 2014.

PY - 2014/11/7

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N2 - A reaction-based chemosensor (AF-1) was designed, synthesized and applied as an optical approach for quantitative measurement of F- in MeCN. In the presence of F-, selective fluoride-assisted desilylation instantly gave colorimetric and fluorogenic signals, providing a dual-optical channel for the detection of F-. 1H NMR titration was carried out to investigate the desilylation process, revealing F- triggered rapid cleavage of Si-O bond in trimethylsilyl ether. AF-1 exhibited high sensitivity and selectivity to F- over other anions. The detection limit to F- was calculated to be 0.05 ppm.

AB - A reaction-based chemosensor (AF-1) was designed, synthesized and applied as an optical approach for quantitative measurement of F- in MeCN. In the presence of F-, selective fluoride-assisted desilylation instantly gave colorimetric and fluorogenic signals, providing a dual-optical channel for the detection of F-. 1H NMR titration was carried out to investigate the desilylation process, revealing F- triggered rapid cleavage of Si-O bond in trimethylsilyl ether. AF-1 exhibited high sensitivity and selectivity to F- over other anions. The detection limit to F- was calculated to be 0.05 ppm.

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Investigation of desilylation in the recognition mechanism to fluoride by a 1,8-naphthalimide derivative

Abstract

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