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Six-fold C-H borylation of hexa-peri-hexabenzocoronene.

ABSTRACT: 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 ?-donation of boryl groups.

SUBMITTER: Nagase M

PROVIDER: S-EPMC7082694 | biostudies-literature | 2020

REPOSITORIES: biostudies-literature

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Six-fold C-H borylation of hexa-peri-hexabenzocoronene.

Nagase Mai M Kato Kenta K Yagi Akiko A Segawa Yasutomo Y Itami Kenichiro K

Beilstein journal of organic chemistry 20200313

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 w ...[more]

PMID: 32256855

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