FRET-derived ratiometric fluorescence sensor for Cu2+

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

Research output: Contribution to journalArticle

116 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

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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