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Issue 28, 2019
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Synthesis and characterization of bent fluorine-containing donor–π-acceptor molecules as intense luminophores with large Stokes shifts

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Abstract

Herein, we prepared novel bent fluorine-containing donor–π-acceptor (D–π-A) molecules from commercially available octafluorocyclopentene using a facile two-step procedure, revealing that the above molecules absorb UV-light and exhibit yellow photoluminescence (PL) with high PL efficiencies (ΦPL) in solution. The corresponding Stokes shifts exceeded 10 000 cm−1, and the maximum PL wavelength (λPL) strongly depended on solvent polarity or intermolecular interactions in the solid state. On the basis of a Lippert–Mataga plot, PL was confidently assigned to radiative relaxation from an intramolecular charge-transfer excited state. Moreover, the synthesized luminophores showed intense PL even in the crystalline state and exhibited alkoxy chain length-dependent PL behavior (e.g., high ΦPL, λPL = 486–540 nm).

Graphical abstract: Synthesis and characterization of bent fluorine-containing donor–π-acceptor molecules as intense luminophores with large Stokes shifts

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Supplementary files

Article information


Submitted
05 Jun 2019
Accepted
01 Jul 2019
First published
02 Jul 2019

Org. Biomol. Chem., 2019,17, 6911-6919
Article type
Paper

Synthesis and characterization of bent fluorine-containing donor–π-acceptor molecules as intense luminophores with large Stokes shifts

S. Yamada, A. Nishizawa, M. Morita, T. Hosokai, Y. Okabayashi, T. Agou, T. Hosoya, T. Kubota and T. Konno, Org. Biomol. Chem., 2019, 17, 6911
DOI: 10.1039/C9OB01300H

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