FRET-derived ratiometric fluorescence sensor for Cu2+

Hyun Jung Kim; Sun Young Park; Sangwoon Yoon; Jong Seung Kim

doi:10.1016/j.tet.2007.11.063

FRET-derived ratiometric fluorescence sensor for Cu²⁺

Hyun Jung Kim, Sun Young Park, Sangwoon Yoon, Jong Seung Kim

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

125 Citations (Scopus)

Abstract

New N-(pyrenylmethyl)naphtho-azacrown-5 (1) was synthesized as an 'On-Off' fluorescent chemosensor for Cu²⁺. Excited at 240 nm corresponding to the absorption of naphthalene unit (energy donor) of 1, emission at 380 nm from pyrene unit (energy acceptor) is observed, indicating that intramolecular fluorescence resonance energy transfer (FRET-On) occurs in 1. When Cu²⁺ is added to a solution of 1, however, the fluorescence of pyrene is strongly quenched (FRET-Off) whereas that of naphthalene group is revived. Such FRET 'On-Off' behavior of 1 is observed only in the case of Cu²⁺ binding, but not for other metal cations. The high selectivity of 1 toward Cu²⁺ can be potentially applied to a new kind of FRET-based chemosensor. The FRET On-Off behavior is supported by computational studies. The calculated molecular orbitals of HOMO and LUMOs suggest the excited-state interactions leading to FRET from naphthalene to pyrene in 1, but no electron density changes in 1·Cu²⁺ complex.

Original language	English
Pages (from-to)	1294-1300
Number of pages	7
Journal	Tetrahedron
Volume	64
Issue number	7
DOIs	https://doi.org/10.1016/j.tet.2007.11.063
Publication status	Published - 2008 Feb 11

Bibliographical note

Funding Information:
This work was supported by the SRC program (R11-2005-008-02001-0(2007)), the Korea Research Foundation grant (KRF-2006-331-C00141) and Seoul Fellowship for H.J.K.

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2007.11.063

Cite this

@article{460bd076acdf4e1f9b078c95e142dcaf,

title = "FRET-derived ratiometric fluorescence sensor for Cu2+",

abstract = "New N-(pyrenylmethyl)naphtho-azacrown-5 (1) was synthesized as an 'On-Off' fluorescent chemosensor for Cu2+. Excited at 240 nm corresponding to the absorption of naphthalene unit (energy donor) of 1, emission at 380 nm from pyrene unit (energy acceptor) is observed, indicating that intramolecular fluorescence resonance energy transfer (FRET-On) occurs in 1. When Cu2+ is added to a solution of 1, however, the fluorescence of pyrene is strongly quenched (FRET-Off) whereas that of naphthalene group is revived. Such FRET 'On-Off' behavior of 1 is observed only in the case of Cu2+ binding, but not for other metal cations. The high selectivity of 1 toward Cu2+ can be potentially applied to a new kind of FRET-based chemosensor. The FRET On-Off behavior is supported by computational studies. The calculated molecular orbitals of HOMO and LUMOs suggest the excited-state interactions leading to FRET from naphthalene to pyrene in 1, but no electron density changes in 1·Cu2+ complex.",

author = "Kim, {Hyun Jung} and Park, {Sun Young} and Sangwoon Yoon and Kim, {Jong Seung}",

note = "Funding Information: This work was supported by the SRC program (R11-2005-008-02001-0(2007)), the Korea Research Foundation grant (KRF-2006-331-C00141) and Seoul Fellowship for H.J.K. ",

year = "2008",

month = feb,

day = "11",

doi = "10.1016/j.tet.2007.11.063",

language = "English",

volume = "64",

pages = "1294--1300",

journal = "Tetrahedron",

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T1 - FRET-derived ratiometric fluorescence sensor for Cu2+

AU - Kim, Hyun Jung

AU - Park, Sun Young

AU - Yoon, Sangwoon

AU - Kim, Jong Seung

N1 - Funding Information: This work was supported by the SRC program (R11-2005-008-02001-0(2007)), the Korea Research Foundation grant (KRF-2006-331-C00141) and Seoul Fellowship for H.J.K.

PY - 2008/2/11

Y1 - 2008/2/11

N2 - New N-(pyrenylmethyl)naphtho-azacrown-5 (1) was synthesized as an 'On-Off' fluorescent chemosensor for Cu2+. Excited at 240 nm corresponding to the absorption of naphthalene unit (energy donor) of 1, emission at 380 nm from pyrene unit (energy acceptor) is observed, indicating that intramolecular fluorescence resonance energy transfer (FRET-On) occurs in 1. When Cu2+ is added to a solution of 1, however, the fluorescence of pyrene is strongly quenched (FRET-Off) whereas that of naphthalene group is revived. Such FRET 'On-Off' behavior of 1 is observed only in the case of Cu2+ binding, but not for other metal cations. The high selectivity of 1 toward Cu2+ can be potentially applied to a new kind of FRET-based chemosensor. The FRET On-Off behavior is supported by computational studies. The calculated molecular orbitals of HOMO and LUMOs suggest the excited-state interactions leading to FRET from naphthalene to pyrene in 1, but no electron density changes in 1·Cu2+ complex.

AB - New N-(pyrenylmethyl)naphtho-azacrown-5 (1) was synthesized as an 'On-Off' fluorescent chemosensor for Cu2+. Excited at 240 nm corresponding to the absorption of naphthalene unit (energy donor) of 1, emission at 380 nm from pyrene unit (energy acceptor) is observed, indicating that intramolecular fluorescence resonance energy transfer (FRET-On) occurs in 1. When Cu2+ is added to a solution of 1, however, the fluorescence of pyrene is strongly quenched (FRET-Off) whereas that of naphthalene group is revived. Such FRET 'On-Off' behavior of 1 is observed only in the case of Cu2+ binding, but not for other metal cations. The high selectivity of 1 toward Cu2+ can be potentially applied to a new kind of FRET-based chemosensor. The FRET On-Off behavior is supported by computational studies. The calculated molecular orbitals of HOMO and LUMOs suggest the excited-state interactions leading to FRET from naphthalene to pyrene in 1, but no electron density changes in 1·Cu2+ complex.

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