A fluorescent chemosensor for Al3+ based on julolidine and tryptophan moieties

Ye Won Choi; Jae Jun Lee; Eunju Nam; Mi Hee Lim; Cheal Kim

doi:10.1016/j.tet.2016.02.066

A fluorescent chemosensor for Al³⁺ based on julolidine and tryptophan moieties

Ye Won Choi, Jae Jun Lee, Eunju Nam, Mi Hee Lim, Cheal Kim

Dept. of Fine Chemistry

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

32 Scopus citations

Abstract

A new and simple fluorescent chemosensor 1, based on julolidine and tryptophan moieties, has been synthesized and characterized. The sensor 1 displayed a selective and sensitive detecting ability for aluminum (III) ion by 'OFF-ON' fluorescent response in aqueous solution. This sensing mechanism might be due to the inhibition of C=N isomerization, and the activation of chelation enhanced fluorescence (CHEF). This sensing mechanism of 1 for Al³⁺ was supported by theoretical calculations. Moreover, sensor 1 had a low detection limit (6.4 μM), which is below than the WHO recommendation level (7.41 μM) for drinking water. Importantly, the chemosensor 1 could be applied to living cells to detect Al³⁺. Therefore, the sensor 1 can be employed as a practical fluorescent chemosensor for recognition of Al³⁺ in aqueous solution.

Original language	English
Pages (from-to)	1998-2005
Number of pages	8
Journal	Tetrahedron
Volume	72
Issue number	16
DOIs	https://doi.org/10.1016/j.tet.2016.02.066
State	Published - 21 Apr 2016

Keywords

Aluminum ion
C=N isomerization
Cell imaging
CHEF
Fluorescent chemosensor
Theoretical calculations

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10.1016/j.tet.2016.02.066

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title = "A fluorescent chemosensor for Al3+ based on julolidine and tryptophan moieties",

abstract = "A new and simple fluorescent chemosensor 1, based on julolidine and tryptophan moieties, has been synthesized and characterized. The sensor 1 displayed a selective and sensitive detecting ability for aluminum (III) ion by 'OFF-ON' fluorescent response in aqueous solution. This sensing mechanism might be due to the inhibition of C=N isomerization, and the activation of chelation enhanced fluorescence (CHEF). This sensing mechanism of 1 for Al3+ was supported by theoretical calculations. Moreover, sensor 1 had a low detection limit (6.4 μM), which is below than the WHO recommendation level (7.41 μM) for drinking water. Importantly, the chemosensor 1 could be applied to living cells to detect Al3+. Therefore, the sensor 1 can be employed as a practical fluorescent chemosensor for recognition of Al3+ in aqueous solution.",

keywords = "Aluminum ion, C=N isomerization, Cell imaging, CHEF, Fluorescent chemosensor, Theoretical calculations",

author = "Choi, \{Ye Won\} and Lee, \{Jae Jun\} and Eunju Nam and Lim, \{Mi Hee\} and Cheal Kim",

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T1 - A fluorescent chemosensor for Al3+ based on julolidine and tryptophan moieties

AU - Choi, Ye Won

AU - Lee, Jae Jun

AU - Nam, Eunju

AU - Lim, Mi Hee

AU - Kim, Cheal

PY - 2016/4/21

Y1 - 2016/4/21

N2 - A new and simple fluorescent chemosensor 1, based on julolidine and tryptophan moieties, has been synthesized and characterized. The sensor 1 displayed a selective and sensitive detecting ability for aluminum (III) ion by 'OFF-ON' fluorescent response in aqueous solution. This sensing mechanism might be due to the inhibition of C=N isomerization, and the activation of chelation enhanced fluorescence (CHEF). This sensing mechanism of 1 for Al3+ was supported by theoretical calculations. Moreover, sensor 1 had a low detection limit (6.4 μM), which is below than the WHO recommendation level (7.41 μM) for drinking water. Importantly, the chemosensor 1 could be applied to living cells to detect Al3+. Therefore, the sensor 1 can be employed as a practical fluorescent chemosensor for recognition of Al3+ in aqueous solution.

AB - A new and simple fluorescent chemosensor 1, based on julolidine and tryptophan moieties, has been synthesized and characterized. The sensor 1 displayed a selective and sensitive detecting ability for aluminum (III) ion by 'OFF-ON' fluorescent response in aqueous solution. This sensing mechanism might be due to the inhibition of C=N isomerization, and the activation of chelation enhanced fluorescence (CHEF). This sensing mechanism of 1 for Al3+ was supported by theoretical calculations. Moreover, sensor 1 had a low detection limit (6.4 μM), which is below than the WHO recommendation level (7.41 μM) for drinking water. Importantly, the chemosensor 1 could be applied to living cells to detect Al3+. Therefore, the sensor 1 can be employed as a practical fluorescent chemosensor for recognition of Al3+ in aqueous solution.

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KW - Cell imaging

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KW - Fluorescent chemosensor

KW - Theoretical calculations

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A fluorescent chemosensor for Al³⁺ based on julolidine and tryptophan moieties

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Keywords

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