Six-fold C–H borylation of hexa-peri-hexabenzocoronene
2020 ◽
Vol 16
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pp. 391-397
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Keyword(s):
X Ray
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Hexa-peri-hexabenzocoronene (HBC) is known to be a poorly soluble polycyclic aromatic hydrocarbon for which direct functionalization methods have been very limited. Herein, the synthesis of hexaborylated HBC from unsubstituted HBC is described. Iridium-catalyzed six-fold C–H borylation of HBC was successfully achieved by screening solvents. The crystal structure of hexaborylated HBC was confirmed via X-ray crystallography. Optoelectronic properties of the thus-obtained hexaborylated HBC were analyzed with the support of density functional theory calculations. The spectra revealed a bathochromic shift of absorption bands compared with unsubstituted HBC under the effect of the σ-donation of boryl groups.
2021 ◽
2017 ◽
Vol 73
(6)
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pp. 1032-1042
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2017 ◽
Vol 73
(6)
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pp. 1179-1193
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2007 ◽
Vol 129
(14)
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pp. 4193-4205
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2011 ◽
Vol 991
(1-3)
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pp. 158-161
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2006 ◽
Vol 794
(1-3)
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pp. 244-250
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