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Design, Synthesis, and Characterization of Functionalized Silepins: High Quantum Yield Blue Emitters

Lookup NU author(s): Dr Ross Harrington, Emeritus Professor Bill Clegg

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Abstract

The synthesis of a family of 1,1-dimethyldibenzo-[bf]silepin derivatives, substituted with. donor groups of various donor strength and conjugation length in the positions meta or para to the silepin silicon, is presented. The compounds were characterized by NMR, UV-vis, and fluorescence spectroscopy, as well as with cyclic voltammetry and DFT computations. One of the meta series was characterized by X-ray crystallography. All compounds show red-shifts in onset absorption and emission maxima compared to the parent 1,1-dimethyldibenzo[bf]silepin, but all exhibit blue fluorescence with quantum yields ranging from 0.46 to 0.93 for the meta series and from 0.09 to 0.46 for the para derivatives. The data suggest that, for the meta series, the primary absorption is of pi-pi* character, while in the para series, for strongly donating groups, transitions from low-lying pi orbitals to the LUMO+1 orbital, which has contributions from the C-Si-C sigma* orbitals, are charge-transfer in character. The phenyl-substituted derivatives can be converted to borepins via transmetalation with BBr3, but other strategies are necessary to prepare borepins with other donor groups.


Publication metadata

Author(s): Mercier LG, Furukawa S, Piers WE, Wakamiya A, Yamaguchi S, Parvez M, Harrington RW, Clegg W

Publication type: Article

Publication status: Published

Journal: Organometallics

Year: 2011

Volume: 30

Issue: 6

Pages: 1719-1729

Print publication date: 28/02/2011

ISSN (print): 0276-7333

ISSN (electronic): 1520-6041

Publisher: American Chemical Society

URL: http://dx.doi.org/10.1021/om2000597

DOI: 10.1021/om2000597


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