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Issue 3, 2015
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Synthesis, structures and electrochemical and photophysical properties of anilido-benzoxazole boron difluoride (ABB) complexes

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Abstract

A new series of four-ring-fused π-conjugated anilido-benzoxazole boron difluoride (ABB) dyes were synthesized by employing an unsymmetrical bidentate ligand under a mild reaction condition. X-ray structural analysis demonstrated that the four-ring-fused π-conjugated skeleton is nearly coplanar, and almost orthogonal to the side anilido phenyl group with dihedral angles of 74–86°. The synthesized complexes exhibit very bright luminescence in solution (Φf = 0.45–0.96 in CH2Cl2) and in the solid-state (Φf = 0.07–0.37). These complexes show a larger Stokes shift (56–128 nm) than the well-known boron dipyrromethene dyes (8–12 nm, in most cases). The role of molecular packing patterns elucidated by the assistance of their X-ray crystal structures rationalizes the solid-state fluorescence. One of the tested compounds displayed aggregation induced emission (AIE). First-principle-based quantum-chemical studies were carried out on complexes 1–6. Time-dependent DFT (TD-DFT) calculations support the experimental results. The participation of the anilido phenyl moiety and the fluorine atoms was found to be negligible in the LUMO orbitals.

Graphical abstract: Synthesis, structures and electrochemical and photophysical properties of anilido-benzoxazole boron difluoride (ABB) complexes

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Publication details

The article was received on 03 Oct 2014, accepted on 04 Nov 2014 and first published on 07 Nov 2014


Article type: Paper
DOI: 10.1039/C4DT03052D
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Dalton Trans., 2015,44, 1120-1129

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    Synthesis, structures and electrochemical and photophysical properties of anilido-benzoxazole boron difluoride (ABB) complexes

    Y. Meesala, V. Kavala, H. Chang, T. Kuo, C. Yao and W. Lee, Dalton Trans., 2015, 44, 1120
    DOI: 10.1039/C4DT03052D

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