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 language | English |
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Pages (from-to) | 1120-1129 |
Number of pages | 10 |
Journal | Dalton Transactions |
Volume | 44 |
Issue number | 3 |
DOIs | |
Publication status | Published - 2014 Nov 24 |
ASJC Scopus subject areas
- Inorganic Chemistry
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CCDC 966880: Experimental Crystal Structure Determination
Meesala, Y. (Creator), Kavala, V. (Creator), Chang, H. (Creator), Kuo, T. (Creator), Yao, C. (Creator) & Lee, W. (Creator), Unknown Publisher, 2014
DOI: 10.5517/cc11g3p9, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc11g3p9&sid=DataCite
Dataset
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CCDC 966883: Experimental Crystal Structure Determination
Meesala, Y. (Creator), Kavala, V. (Creator), Chang, H. (Creator), Kuo, T. (Creator), Yao, C. (Creator) & Lee, W. (Creator), Unknown Publisher, 2014
DOI: 10.5517/cc11g3sd, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc11g3sd&sid=DataCite
Dataset
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CCDC 966878: Experimental Crystal Structure Determination
Meesala, Y. (Creator), Kavala, V. (Creator), Chang, H. (Creator), Kuo, T. (Creator), Yao, C. (Creator) & Lee, W. (Creator), Unknown Publisher, 2014
DOI: 10.5517/cc11g3m7, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc11g3m7&sid=DataCite
Dataset