Evaluation of a simple and novel fluorescent anion sensor, 4-quinolone, and modification of the emission color by substitutions based on molecular orbital calculations

Junzo Hirano, Kenji Hamase, Kiyoshi Zaitsu

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

4-Quinolone (4-QO) was evaluated as a simple and novel fluorescent anion sensor, and the modification of its emission color was carried out. The series of 4-QO derivatives having molecular orbitals with different energy levels was designed by substitutions at the 6 and 7 positions based on the molecular orbital calculations. All derivatives showed drastic fluorescence enhancements in the presence of F- via the intramolecular charge transfer mechanism, and the successful modification of the emission color was achieved. The anion-induced emission colors of these derivatives as well as their binding affinities for F- could be predicted by ab initio quantum chemical calculations, indicating that the present calculations are useful in designing new anion sensors.

Original languageEnglish
Pages (from-to)10065-10071
Number of pages7
JournalTetrahedron
Volume62
Issue number43
DOIs
Publication statusPublished - Oct 23 2006

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4-Quinolones
Orbital calculations
Molecular orbitals
Anions
Substitution reactions
Color
Derivatives
Sensors
Electron energy levels
Charge transfer
Fluorescence

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Evaluation of a simple and novel fluorescent anion sensor, 4-quinolone, and modification of the emission color by substitutions based on molecular orbital calculations. / Hirano, Junzo; Hamase, Kenji; Zaitsu, Kiyoshi.

In: Tetrahedron, Vol. 62, No. 43, 23.10.2006, p. 10065-10071.

Research output: Contribution to journalArticle

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