Herein we devise and execute a new synthesis of a pristine boron-doped nanographene. Our target boron-doped nanographene was designed based on DFT calculations to possess a low LUMO energy level and a narrow band gap derived from its precise geometry and B-doping arrangement. Our synthesis of this target, a doubly B-doped hexabenzopentacene (B -HBP), employs six net C-H borylations of an alkene, comprising consecutive hydroboration/electrophilic borylation/dehydrogenation and BBr /AlCl /2,6-dichloropyridine-mediated C-H borylation steps. As predicted by our calculations, B -HBP absorbs strongly in the visible region and emits in the NIR up to 1150 nm in o-dichlorobenzene solutions. Furthermore, B -HBP possesses a very low LUMO level, showing two reversible reductions at -1.00 V and -1.17 V vs. Fc /Fc. Our methodology is surprisingly selective despite its implementation of unfunctionalized precursors and offers a new approach to the synthesis of pristine B-doped polycyclic aromatic hydrocarbons.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC9305547 | PMC |
| http://dx.doi.org/10.1002/anie.202115746 | DOI Listing |
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