Anion-induced ring-opening of fluorescein spirolactam: fluorescent OFF-ON

Jia Sheng Wu; Hyun Jung Kim; Min Hee Lee; Jun Hee Yoon; Joung Hae Lee; Jong Seung Kim

doi:10.1016/j.tetlet.2007.03.060

Anion-induced ring-opening of fluorescein spirolactam: fluorescent OFF-ON

Jia Sheng Wu, Hyun Jung Kim, Min Hee Lee, Jun Hee Yoon, Joung Hae Lee, Jong Seung Kim

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

31 Citations (Scopus)

Abstract

N-(2,7-Dichlorofluorescein)lactam-N′-phenylthiourea (L) was developed as a colorimetric and fluorescent chemosensor for anions such as AcO^-, F^- and H₂ PO₄^-. The addition of AcO^- anion to the solution of L in CH₃CN results in a distinct fluorescence "ON" observation as well as color change (from colorless to pink). The H-bonding interaction between AcO^- anion and thiourea moiety of L induced the ring-opening of the spirolactam of fluorescein moiety, which gave rise to the dual chromo- and fluorogenic changes.

Original language	English
Pages (from-to)	3159-3162
Number of pages	4
Journal	Tetrahedron Letters
Volume	48
Issue number	18
DOIs	https://doi.org/10.1016/j.tetlet.2007.03.060
Publication status	Published - 2007 Apr 30
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2007.03.060

Cite this

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title = "Anion-induced ring-opening of fluorescein spirolactam: fluorescent OFF-ON",

abstract = "N-(2,7-Dichlorofluorescein)lactam-N′-phenylthiourea (L) was developed as a colorimetric and fluorescent chemosensor for anions such as AcO-, F- and H2 PO4-. The addition of AcO- anion to the solution of L in CH3CN results in a distinct fluorescence {"}ON{"} observation as well as color change (from colorless to pink). The H-bonding interaction between AcO- anion and thiourea moiety of L induced the ring-opening of the spirolactam of fluorescein moiety, which gave rise to the dual chromo- and fluorogenic changes.",

author = "Wu, {Jia Sheng} and Kim, {Hyun Jung} and Lee, {Min Hee} and Yoon, {Jun Hee} and Lee, {Joung Hae} and Kim, {Jong Seung}",

note = "Funding Information: This work was supported by the SRC program (R11-2005-008-02001-0(2006)), Basic Science Research of KOSEF (R01-2006-000-10001-0) and BK21. ",

year = "2007",

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doi = "10.1016/j.tetlet.2007.03.060",

language = "English",

volume = "48",

pages = "3159--3162",

journal = "Tetrahedron Letters",

issn = "0040-4039",

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number = "18",

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TY - JOUR

T1 - Anion-induced ring-opening of fluorescein spirolactam

T2 - fluorescent OFF-ON

AU - Wu, Jia Sheng

AU - Kim, Hyun Jung

AU - Lee, Min Hee

AU - Yoon, Jun Hee

AU - Lee, Joung Hae

AU - Kim, Jong Seung

N1 - Funding Information: This work was supported by the SRC program (R11-2005-008-02001-0(2006)), Basic Science Research of KOSEF (R01-2006-000-10001-0) and BK21.

PY - 2007/4/30

Y1 - 2007/4/30

N2 - N-(2,7-Dichlorofluorescein)lactam-N′-phenylthiourea (L) was developed as a colorimetric and fluorescent chemosensor for anions such as AcO-, F- and H2 PO4-. The addition of AcO- anion to the solution of L in CH3CN results in a distinct fluorescence "ON" observation as well as color change (from colorless to pink). The H-bonding interaction between AcO- anion and thiourea moiety of L induced the ring-opening of the spirolactam of fluorescein moiety, which gave rise to the dual chromo- and fluorogenic changes.

AB - N-(2,7-Dichlorofluorescein)lactam-N′-phenylthiourea (L) was developed as a colorimetric and fluorescent chemosensor for anions such as AcO-, F- and H2 PO4-. The addition of AcO- anion to the solution of L in CH3CN results in a distinct fluorescence "ON" observation as well as color change (from colorless to pink). The H-bonding interaction between AcO- anion and thiourea moiety of L induced the ring-opening of the spirolactam of fluorescein moiety, which gave rise to the dual chromo- and fluorogenic changes.

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U2 - 10.1016/j.tetlet.2007.03.060

DO - 10.1016/j.tetlet.2007.03.060

M3 - Article

AN - SCOPUS:34047101287

SN - 0040-4039

VL - 48

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 18

ER -

Anion-induced ring-opening of fluorescein spirolactam: fluorescent OFF-ON

Abstract

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