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, M. L. Turner

Research output: Contribution to journalArticle

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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%.
Original languageEnglish
Pages (from-to)5144-5151
Number of pages8
JournalChemical Science
Volume6
Issue number9
DOIs
Publication statusPublished - 12 Jun 2015
Externally publishedYes

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Electron affinity
Semiconducting organic compounds
Electron energy levels
Energy gap
Tuning
Boron
Alkylation
Electroluminescence
Organic light emitting diodes (OLED)
Quantum yield
Water
benzo-1,2,3-thiadiazole

Cite this

Crossley, D. L. ; Cade, I. A. ; Clark, E. R. ; Escande, A. ; Humphries, M. J. ; King, S. M. ; Vitorica-Yrezabal, I. ; Ingleson, M. J. ; Turner, M. L. / Enhancing electron affinity and tuning band gap in donor-acceptor organic semiconductors by benzothiadiazole directed C-H borylation. In: Chemical Science. 2015 ; Vol. 6, No. 9. pp. 5144-5151.
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Crossley, DL, Cade, IA, Clark, ER, Escande, A, Humphries, MJ, King, SM, Vitorica-Yrezabal, I, Ingleson, MJ & Turner, ML 2015, 'Enhancing electron affinity and tuning band gap in donor-acceptor organic semiconductors by benzothiadiazole directed C-H borylation', Chemical Science, vol. 6, no. 9, pp. 5144-5151. https://doi.org/10.1039/c5sc01800e

Enhancing electron affinity and tuning band gap in donor-acceptor organic semiconductors by benzothiadiazole directed C-H borylation. / Crossley, D. L.; Cade, I. A.; Clark, E. R.; Escande, A.; Humphries, M. J.; King, S. M.; Vitorica-Yrezabal, I.; Ingleson, M. J.; Turner, M. L.

In: Chemical Science, Vol. 6, No. 9, 12.06.2015, p. 5144-5151.

Research output: Contribution to journalArticle

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T1 - Enhancing electron affinity and tuning band gap in donor-acceptor organic semiconductors by benzothiadiazole directed C-H borylation

AU - Crossley, D. L.

AU - Cade, I. A.

AU - Clark, E. R.

AU - Escande, A.

AU - Humphries, M. J.

AU - King, S. M.

AU - Vitorica-Yrezabal, I.

AU - Ingleson, M. J.

AU - Turner, M. L.

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