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Issue 9, 2015
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Enhancing electron affinity and tuning band gap in donor–acceptor organic semiconductors by benzothiadiazole directed C–H borylation

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Abstract

Electrophilic borylation using BCl3 and benzothiadiazole to direct the C–H functionalisation of an adjacent aromatic unit produces fused boracyclic materials with minimally changed HOMO energy levels but significantly reduced LUMO energy levels. In situ alkylation and arylation at boron using Al(alkyl)3 or Zn(aryl)2 is facile and affords boracycles that possess excellent stability towards protic solvents, including water, and display large bathochromic shifts leading to far red/NIR emission in the solid state with quantum yields of up to 34%. Solution fabricated OLEDs with far red/NIR electroluminescence are reported with EQEs > 0.4%.

Graphical abstract: Enhancing electron affinity and tuning band gap in donor–acceptor organic semiconductors by benzothiadiazole directed C–H borylation

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Publication details

The article was received on 18 May 2015, accepted on 06 Jun 2015 and first published on 12 Jun 2015


Article type: Edge Article
DOI: 10.1039/C5SC01800E
Citation: Chem. Sci., 2015,6, 5144-5151
  • Open access: Creative Commons BY-NC license
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    Enhancing electron affinity and tuning band gap in donor–acceptor organic semiconductors by benzothiadiazole directed C–H borylation

    D. L. Crossley, I. A. Cade, E. R. Clark, A. Escande, M. J. Humphries, S. M. King, I. Vitorica-Yrezabal, M. J. Ingleson and M. L. Turner, Chem. Sci., 2015, 6, 5144
    DOI: 10.1039/C5SC01800E

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