%0 Journal Article %1 Muetzel_2022 %A Mützel, Carina %A Farrell, Jeffrey M. %A Shoyama, Kazutaka %A Würthner, Frank %D 2022 %I Wiley %J Angew. Chem. Int. Ed. %K myown %R 10.1002/anie.202115746 %T 12b,24b-Diborahexabenzoa,c,fg,l,n,qrpentacene: A Low-LUMO Boron-Doped Polycyclic Aromatic Hydrocarbon %U https://doi.org/10.1002%2Fanie.202115746 %X 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 (B2-HBP), employs six net C H borylations of an alkene, comprising consecutive hydroboration/electrophilic borylation/dehydrogenation and BBr3/AlCl3/2,6-dichloropyridine- mediated C H borylation steps. As predicted by our calculations, B2-HBP absorbs strongly in the visible region and emits in the NIR up to 1150 nm in o-dichlorobenzene solutions. Furthermore, B2-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.

@article{Muetzel_2022, abstract = {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 (B2-HBP), employs six net C H borylations of an alkene, comprising consecutive hydroboration/electrophilic borylation/dehydrogenation and BBr3/AlCl3/2,6-dichloropyridine- mediated C H borylation steps. As predicted by our calculations, B2-HBP absorbs strongly in the visible region and emits in the NIR up to 1150 nm in o-dichlorobenzene solutions. Furthermore, B2-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.}, added-at = {2022-01-17T10:08:27.000+0100}, author = {Mützel, Carina and Farrell, Jeffrey M. and Shoyama, Kazutaka and Würthner, Frank}, biburl = {https://www.bibsonomy.org/bibtex/2155187ebb3b4e7c6f0033b75d486c49e/wuerthner_group}, doi = {10.1002/anie.202115746}, interhash = {0b16f837fbee8005d1d7681f6dc17983}, intrahash = {155187ebb3b4e7c6f0033b75d486c49e}, journal = {Angew. Chem. Int. Ed.}, keywords = {myown}, month = jan, publisher = {Wiley}, timestamp = {2022-01-17T10:08:27.000+0100}, title = {12b,24b-Diborahexabenzo[a,c,fg,l,n,qr]pentacene: A Low-LUMO Boron-Doped Polycyclic Aromatic Hydrocarbon}, url = {https://doi.org/10.1002%2Fanie.202115746}, year = 2022 }