New regioisomeric naphthol-thiazole based 'turn-on' fluorescent chemosensor for Al3+

Aasif Helal; Hyun Gon Kim; Manik Kumer Ghosh; Cheol Ho Choi; Sung Hong Kim; Hong Seok Kim

doi:10.1016/j.tet.2013.09.038

New regioisomeric naphthol-thiazole based 'turn-on' fluorescent chemosensor for Al³⁺

Aasif Helal, Hyun Gon Kim, Manik Kumer Ghosh, Cheol Ho Choi, Sung Hong Kim, Hong Seok Kim

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36 Scopus citations

Abstract

Two new reactive and highly selective turn-on fluorescent chemosensors based on the position of ring annulation of the naphthalene-thiazole moiety for aluminum ions in ethanol, were synthesized and investigated. It was found that sensors 2 and 4 exhibited a remarkable enhancement of emission upon complexation with Al³⁺. A TD-B3LYP/6-31G(d,p) calculation was performed to characterize the nature of the fluorescence behavior of sensors 2 and 4 upon Al³⁺ complexation. The mechanism of fluorescence was based on the cation promoted hydrolysis of ester and subsequent complexation. The combination of experimental and computational analyses provides a more complete understanding of the molecular level origin of these types of unique photophysical properties.

Original language	English
Pages (from-to)	9600-9608
Number of pages	9
Journal	Tetrahedron
Volume	69
Issue number	46
DOIs	https://doi.org/10.1016/j.tet.2013.09.038
State	Published - 18 Nov 2013

Keywords

Al-promoted hydrolysis
Al-selective
Fluorescent chemosensor
Regioisomeric naphthol-thiazole
Turn-on

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10.1016/j.tet.2013.09.038

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title = "New regioisomeric naphthol-thiazole based 'turn-on' fluorescent chemosensor for Al3+",

abstract = "Two new reactive and highly selective turn-on fluorescent chemosensors based on the position of ring annulation of the naphthalene-thiazole moiety for aluminum ions in ethanol, were synthesized and investigated. It was found that sensors 2 and 4 exhibited a remarkable enhancement of emission upon complexation with Al3+. A TD-B3LYP/6-31G(d,p) calculation was performed to characterize the nature of the fluorescence behavior of sensors 2 and 4 upon Al3+ complexation. The mechanism of fluorescence was based on the cation promoted hydrolysis of ester and subsequent complexation. The combination of experimental and computational analyses provides a more complete understanding of the molecular level origin of these types of unique photophysical properties.",

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author = "Aasif Helal and Kim, {Hyun Gon} and Ghosh, {Manik Kumer} and Choi, {Cheol Ho} and Kim, {Sung Hong} and Kim, {Hong Seok}",

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T1 - New regioisomeric naphthol-thiazole based 'turn-on' fluorescent chemosensor for Al3+

AU - Helal, Aasif

AU - Kim, Hyun Gon

AU - Ghosh, Manik Kumer

AU - Choi, Cheol Ho

AU - Kim, Sung Hong

AU - Kim, Hong Seok

PY - 2013/11/18

Y1 - 2013/11/18

N2 - Two new reactive and highly selective turn-on fluorescent chemosensors based on the position of ring annulation of the naphthalene-thiazole moiety for aluminum ions in ethanol, were synthesized and investigated. It was found that sensors 2 and 4 exhibited a remarkable enhancement of emission upon complexation with Al3+. A TD-B3LYP/6-31G(d,p) calculation was performed to characterize the nature of the fluorescence behavior of sensors 2 and 4 upon Al3+ complexation. The mechanism of fluorescence was based on the cation promoted hydrolysis of ester and subsequent complexation. The combination of experimental and computational analyses provides a more complete understanding of the molecular level origin of these types of unique photophysical properties.

AB - Two new reactive and highly selective turn-on fluorescent chemosensors based on the position of ring annulation of the naphthalene-thiazole moiety for aluminum ions in ethanol, were synthesized and investigated. It was found that sensors 2 and 4 exhibited a remarkable enhancement of emission upon complexation with Al3+. A TD-B3LYP/6-31G(d,p) calculation was performed to characterize the nature of the fluorescence behavior of sensors 2 and 4 upon Al3+ complexation. The mechanism of fluorescence was based on the cation promoted hydrolysis of ester and subsequent complexation. The combination of experimental and computational analyses provides a more complete understanding of the molecular level origin of these types of unique photophysical properties.

KW - Al-promoted hydrolysis

KW - Al-selective

KW - Fluorescent chemosensor

KW - Regioisomeric naphthol-thiazole

KW - Turn-on

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DO - 10.1016/j.tet.2013.09.038

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JF - Tetrahedron

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New regioisomeric naphthol-thiazole based 'turn-on' fluorescent chemosensor for Al³⁺

Abstract

Keywords

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