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

Yedukondalu Meesala, Veerababurao Kavala, Hao Ching Chang, Ting Shen Kuo, Ching-Fa Yao, Way-Zen Lee

Research output: Contribution to journalArticle

18 Citations (Scopus)

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. This journal is

Original languageEnglish
Pages (from-to)1120-1129
Number of pages10
JournalDalton Transactions
Volume44
Issue number3
DOIs
Publication statusPublished - 2014 Nov 24

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Benzoxazoles
Coloring Agents
X-Rays
X rays
Boron
Fluorine
Dihedral angle
Luminescence
Skeleton
Discrete Fourier transforms
Structural analysis
Agglomeration
Crystal structure
Fluorescence
Ligands
Atoms
boron difluoride

ASJC Scopus subject areas

  • Inorganic Chemistry

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Synthesis, structures and electrochemical and photophysical properties of anilido-benzoxazole boron difluoride (ABB) complexes. / Meesala, Yedukondalu; Kavala, Veerababurao; Chang, Hao Ching; Kuo, Ting Shen; Yao, Ching-Fa; Lee, Way-Zen.

In: Dalton Transactions, Vol. 44, No. 3, 24.11.2014, p. 1120-1129.

Research output: Contribution to journalArticle

Meesala, Yedukondalu ; Kavala, Veerababurao ; Chang, Hao Ching ; Kuo, Ting Shen ; Yao, Ching-Fa ; Lee, Way-Zen. / Synthesis, structures and electrochemical and photophysical properties of anilido-benzoxazole boron difluoride (ABB) complexes. In: Dalton Transactions. 2014 ; Vol. 44, No. 3. pp. 1120-1129.
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