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

Mai Nagase, Kenta Kato, Akiko Yagi, Yasutomo Segawa, Kenichiro Itami

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

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. Iridiumcatalyzed 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 ó-donation of boryl groups.

Original languageEnglish
Pages (from-to)391-397
Number of pages7
JournalBeilstein Journal of Organic Chemistry
Volume16
DOIs
Publication statusPublished - 2020 Mar 13
Externally publishedYes

Keywords

  • C-H borylation
  • Hexa-peri-hexabenzocoronene
  • Iridium catalyst
  • X-ray crystallography

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Six-fold C-H borylation of hexa-peri-hexabenzocoronene'. Together they form a unique fingerprint.

Cite this