Synthesis and photophysical properties of difluoroboronated β-diketones with the fluorene moiety that have high fluorescence quantum yields

Yurie Suwa, Minoru Yamaji, Hideki Okamoto

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

Difluoroboronate β-diketones, compounds 1 having the fluorene moiety and the phenyl groups as well as the ligating precursors of the corresponding β-diketones, compounds 2 were synthesized. The photophysical features of compounds 1 were investigated based on the measurements of fluorescence yields and lifetimes, and transient absorption. Compounds 1 are significantly fluorescent with quantum yields of ca. 0.95 in acetonitrile and ca. 0.90 in chloroform. Fluorescence from compounds 1 was observed also in the solid state. Observation of extremely weak triplet-triplet absorption spectra of compounds 1 verifies the large fluorescence quantum yields.

Original languageEnglish
JournalTetrahedron Letters
DOIs
Publication statusAccepted/In press - Jan 27 2016

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Quantum yield
Fluorescence
Chloroform
Absorption spectra
Observation
fluorene

Keywords

  • Claisen condensation
  • Difluoroboronate β-diketones
  • Fluorescence lifetime
  • Fluorescence quantum yield
  • Triplet-triplet absorption

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

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AU - Yamaji, Minoru

AU - Okamoto, Hideki

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N2 - Difluoroboronate β-diketones, compounds 1 having the fluorene moiety and the phenyl groups as well as the ligating precursors of the corresponding β-diketones, compounds 2 were synthesized. The photophysical features of compounds 1 were investigated based on the measurements of fluorescence yields and lifetimes, and transient absorption. Compounds 1 are significantly fluorescent with quantum yields of ca. 0.95 in acetonitrile and ca. 0.90 in chloroform. Fluorescence from compounds 1 was observed also in the solid state. Observation of extremely weak triplet-triplet absorption spectra of compounds 1 verifies the large fluorescence quantum yields.

AB - Difluoroboronate β-diketones, compounds 1 having the fluorene moiety and the phenyl groups as well as the ligating precursors of the corresponding β-diketones, compounds 2 were synthesized. The photophysical features of compounds 1 were investigated based on the measurements of fluorescence yields and lifetimes, and transient absorption. Compounds 1 are significantly fluorescent with quantum yields of ca. 0.95 in acetonitrile and ca. 0.90 in chloroform. Fluorescence from compounds 1 was observed also in the solid state. Observation of extremely weak triplet-triplet absorption spectra of compounds 1 verifies the large fluorescence quantum yields.

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KW - Triplet-triplet absorption

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