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^*

^*Corresponding author for this work

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

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
Externally published	Yes

Bibliographical note

Funding Information:
This research was supported by Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Science, ICT and Future Planning ( 2013006777 ), and Kyungpook National University Research Fund , 2013.

Keywords

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

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tet.2013.09.038

Cite this

@article{2752b4a590be4442830725f3f2323dd4,

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.",

keywords = "Al-promoted hydrolysis, Al-selective, Fluorescent chemosensor, Regioisomeric naphthol-thiazole, Turn-on",

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

note = "Funding Information: This research was supported by Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Science, ICT and Future Planning ( 2013006777 ), and Kyungpook National University Research Fund , 2013. ",

year = "2013",

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doi = "10.1016/j.tet.2013.09.038",

language = "English",

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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

N1 - Funding Information: This research was supported by Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Science, ICT and Future Planning ( 2013006777 ), and Kyungpook National University Research Fund , 2013.

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

UR - https://www.scopus.com/pages/publications/84885173558

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DO - 10.1016/j.tet.2013.09.038

M3 - Article

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EP - 9608

JO - Tetrahedron

JF - Tetrahedron

IS - 46

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