FRET-derived ratiometric fluorescence sensor for Cu2+

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

Research output: Contribution to journalArticle

113 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 languageEnglish
Pages (from-to)1294-1300
Number of pages7
JournalTetrahedron
Volume64
Issue number7
DOIs
Publication statusPublished - 2008 Feb 11

Fingerprint

Fluorescence
Sensors
Fluorescence Resonance Energy Transfer
Molecular orbitals
Excited states
Carrier concentration
Cations
Metals
Electrons
pyrene
naphthalene

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

FRET-derived ratiometric fluorescence sensor for Cu2+ . / Kim, Hyun Jung; Park, Sun Young; Yoon, Sangwoon; Kim, Jong Seung.

In: Tetrahedron, Vol. 64, No. 7, 11.02.2008, p. 1294-1300.

Research output: Contribution to journalArticle

Kim, Hyun Jung ; Park, Sun Young ; Yoon, Sangwoon ; Kim, Jong Seung. / FRET-derived ratiometric fluorescence sensor for Cu2+ In: Tetrahedron. 2008 ; Vol. 64, No. 7. pp. 1294-1300.
@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}",
year = "2008",
month = "2",
day = "11",
doi = "10.1016/j.tet.2007.11.063",
language = "English",
volume = "64",
pages = "1294--1300",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "7",

}

TY - JOUR

T1 - FRET-derived ratiometric fluorescence sensor for Cu2+

AU - Kim, Hyun Jung

AU - Park, Sun Young

AU - Yoon, Sangwoon

AU - Kim, Jong Seung

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.

UR - http://www.scopus.com/inward/record.url?scp=37649007138&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=37649007138&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2007.11.063

DO - 10.1016/j.tet.2007.11.063

M3 - Article

VL - 64

SP - 1294

EP - 1300

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 7

ER -