Benzoselenadiazole and benzotriazole directed electrophilic C–H borylation of conjugated donor–acceptor materials

Benzoselenadiazole and benzotriazole directed electrophilic borylation using BCl 3 results in the C–H functionalization of an adjacent aromatic unit and produces fused boracycles. Subsequent arylation at boron afforded air and moisture stable products displaying large bathochromic shifts and signifi...

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Published inJournal of materials chemistry. C, Materials for optical and electronic devices Vol. 7; no. 3; pp. 718 - 724
Main Authors Dash, Barada P., Hamilton, Iain, Tate, Daniel J., Crossley, Daniel L., Kim, Ji-Seon, Ingleson, Michael J., Turner, Michael L.
Format Journal Article
LanguageEnglish
Published Cambridge Royal Society of Chemistry 2019
Subjects
Acceptor materials
Benzotriazole
Boron
Boron chlorides
Energy levels
Fluorescence
Molecular orbitals
Organic light emitting diodes
Thin films
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Summary:Benzoselenadiazole and benzotriazole directed electrophilic borylation using BCl 3 results in the C–H functionalization of an adjacent aromatic unit and produces fused boracycles. Subsequent arylation at boron afforded air and moisture stable products displaying large bathochromic shifts and significantly reduced LUMO energy levels. OLEDs fabricated containing borylated benzoselenadiazole derivatives showed emission centered at 723 nm in the near infra-red region of the spectrum.
ISSN:2050-7526
2050-7534
DOI:10.1039/C8TC05131C