A new fluorescent chemosensor for F- based on inhibition of excited-state intramolecular proton transfer

Hyo Sung Jung; Hyun Jung Kim; Jacques Vicens; Jong Seung Kim

doi:10.1016/j.tetlet.2008.12.026

A new fluorescent chemosensor for F^- based on inhibition of excited-state intramolecular proton transfer

Hyo Sung Jung, Hyun Jung Kim, Jacques Vicens, Jong Seung Kim

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

131 Citations (Scopus)

Abstract

New fluorescent chemosensor 1 with two amidoanthraquinone groups (1-AAQs) at the lower rim of p-tert-butylcalix[4]arene has been synthesized. The significant changes of absorption and fluorescence bands show that chemosensor 1 is selective toward fluoride ion (F^-) over other anions such as Cl^-, Br^-, I^-, CH₃COO^-, H₂ PO₄^-, HSO₄^-, and OH^-. The ESIPT process of 1 is inhibited by the fluoride-induced H-bonding followed by deprotonation of NH of the 1-AAQ.

Original language	English
Pages (from-to)	983-987
Number of pages	5
Journal	Tetrahedron Letters
Volume	50
Issue number	9
DOIs	https://doi.org/10.1016/j.tetlet.2008.12.026
Publication status	Published - 2009 Mar 4

Bibliographical note

Funding Information:
This is supported by KOSEF Grant funded by SRC (R11-2005-008-02001-0(2008)), by KRF Grant (KRF-2008-C00426), and by KOSEF-CNRS international collaboration Project (F-01-2006-000-10025-0).

Keywords

Anions
Anthraquinone
Calixarenes
Chemosensor
ESIPT

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tetlet.2008.12.026

Cite this

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title = "A new fluorescent chemosensor for F- based on inhibition of excited-state intramolecular proton transfer",

abstract = "New fluorescent chemosensor 1 with two amidoanthraquinone groups (1-AAQs) at the lower rim of p-tert-butylcalix[4]arene has been synthesized. The significant changes of absorption and fluorescence bands show that chemosensor 1 is selective toward fluoride ion (F-) over other anions such as Cl-, Br-, I-, CH3COO-, H2 PO4-, HSO4-, and OH-. The ESIPT process of 1 is inhibited by the fluoride-induced H-bonding followed by deprotonation of NH of the 1-AAQ.",

keywords = "Anions, Anthraquinone, Calixarenes, Chemosensor, ESIPT",

author = "Jung, {Hyo Sung} and Kim, {Hyun Jung} and Jacques Vicens and Kim, {Jong Seung}",

note = "Funding Information: This is supported by KOSEF Grant funded by SRC (R11-2005-008-02001-0(2008)), by KRF Grant (KRF-2008-C00426), and by KOSEF-CNRS international collaboration Project (F-01-2006-000-10025-0).",

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doi = "10.1016/j.tetlet.2008.12.026",

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AU - Jung, Hyo Sung

AU - Kim, Hyun Jung

AU - Vicens, Jacques

AU - Kim, Jong Seung

N1 - Funding Information: This is supported by KOSEF Grant funded by SRC (R11-2005-008-02001-0(2008)), by KRF Grant (KRF-2008-C00426), and by KOSEF-CNRS international collaboration Project (F-01-2006-000-10025-0).

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Y1 - 2009/3/4

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AB - New fluorescent chemosensor 1 with two amidoanthraquinone groups (1-AAQs) at the lower rim of p-tert-butylcalix[4]arene has been synthesized. The significant changes of absorption and fluorescence bands show that chemosensor 1 is selective toward fluoride ion (F-) over other anions such as Cl-, Br-, I-, CH3COO-, H2 PO4-, HSO4-, and OH-. The ESIPT process of 1 is inhibited by the fluoride-induced H-bonding followed by deprotonation of NH of the 1-AAQ.

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KW - Anthraquinone

KW - Calixarenes

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