Jump to main content
Jump to site search


A modular route to boron doped PAHs by combining borylative cyclisation and electrophilic C–H borylation

Author affiliations

Abstract

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-(specifically not containing direct B–N bonds) 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.

Graphical abstract: A modular route to boron doped PAHs by combining borylative cyclisation and electrophilic C–H borylation

Back to tab navigation

Supplementary files

Publication details

The article was received on 22 Jun 2017, accepted on 28 Sep 2017 and first published on 28 Sep 2017


Article type: Edge Article
DOI: 10.1039/C7SC02793A
Citation: Chem. Sci., 2017, Advance Article
  • Open access: Creative Commons BY license
  •   Request permissions

    A modular route to boron doped PAHs by combining borylative cyclisation and electrophilic C–H borylation

    D. L. Crossley, R. J. Kahan, S. Endres, A. J. Warner, R. A. Smith, J. Cid, J. J. Dunsford, J. E. Jones, I. Vitorica-Yrezabal and M. J. Ingleson, Chem. Sci., 2017, Advance Article , DOI: 10.1039/C7SC02793A

    This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material.

    Reproduced material should be attributed as follows:

    • For reproduction of material from NJC:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
    • For reproduction of material from PCCP:
      [Original citation] - Published by the PCCP Owner Societies.
    • For reproduction of material from PPS:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
    • For reproduction of material from all other RSC journals:
      [Original citation] - Published by The Royal Society of Chemistry.

    Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.

Search articles by author

Spotlight

Advertisements