A Modular Route to Boron Doped PAHs by Combining Borylative Cyclisation and Electrophilic C-H Borylation.

Michael Ingleson, Rachel Kahan, Sebastian Endres, Andrew Warner, Robert Smith, Jessica Cid, Jay Dunsford, Jennifer Jones, Inigo Vitorica-Yrezabal

    Research output: Contribution to journalArticlepeer-review


    Heteroatom doping into polyaromatic hydrocarbons (PAHs) is a powerful approach for modifying key physical properties, however, there are extremely few modular routes that enable facile formation of B-, B2- and B,N- doped PAHs despite the growing importance of these materials. Sequential, one-pot borylative cyclisation / intramolecular electrophilic C-H borylation of naphthyl-alkynes provides a simple new route to access novel B-, B,N- and B2-doped (PAHs). The initial products, dihydronaphthalene / dihydroquinoline B-mesityl PAHs, were reacted with [Ph3C][BF4] / pyridyl base to form the oxidised B-, and B,N-doped PAHs. However, for B-triisopropylphenyl (Trip) PAH congeners oxidation has to be performed prior to Trip installation due to preferential oxidation of an isopropylaryl moiety to the styrene. This alternative sequence enables access to Trip-B-PAHs and to structurally constrained B and B2-PAHs. Analysis of the solid state structures and optoelectronic properties of these PAHs confirm that frontier orbital energies, extended packing structures, Stokes shift and quantum yields all can be rationally modified using this methodology. The simplicity of this synthetic approach makes it a powerful tool for rapidly generating novel bench stable boron doped PAHs, which is important for facilitating further structure-property relationship studies and the wider utilisation of these materials in optoelectronic applications.
    Original languageEnglish
    JournalChemical Science
    Early online date28 Sept 2017
    Publication statusPublished - 2017


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