Dosso, Jacopo ![]() ![]() ![]() ![]() |
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Abstract
In this paper we report a comprehensive account of our synthetic efforts to prepare borazino-doped hexabenzocoronenes using the Friedel-Crafts-type electrophilic aromatic substitution. We showed that hexafluoro-functionalized aryl-borazines, bearing an ortho fluoride leaving group on each N- and B-aryl rings, could lead to cascade-type electrophilic aromatic substitution events in the stepwise C-C bond formation giving higher yields of borazinocoronenes than those obtained with borazine precursors bearing fluoride leaving groups at the ortho positions of the B-aryl substituents. It is with this pathway that an unprecedented boroxadizine-doped PAH featuring a gulf-type periphery could be isolated, and its structure proved through single crystal X-ray diffraction analysis. Mechanistic studies on the stepwise Friedel-Crafts-type cyclisation suggest that the mechanism of the planarization reaction proceeds through extension of the π system. To appraise the doping effect of the boroxadizine unit on the optoelectronic properties of topology-equivalent molecular graphenes, the all-carbon and pyrylium PAH analogues, all featuring a gulf-type periphery, were also prepared. As already shown for the borazino-doped hexabenzocoronene, the replacement of the central benzene ring by its B3N2O congener widens the HOMO-LUMO gap and it dramatically enhances the fluorescence quantum yield.
Item Type: | Article |
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Date Type: | Publication |
Status: | Published |
Schools: | Advanced Research Computing @ Cardiff (ARCCA) Chemistry |
Additional Information: | Published in - Special Issue: Chemical Functionalization of 2D Materials |
Publisher: | Wiley |
ISSN: | 1521-3765 |
Date of First Compliant Deposit: | 13 February 2020 |
Date of Acceptance: | 5 February 2020 |
Last Modified: | 11 Nov 2024 09:45 |
URI: | https://orca.cardiff.ac.uk/id/eprint/129637 |
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