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 σ-donation of boryl groups.
Highlights
Polycyclic aromatic hydrocarbons (PAHs) are beneficial chemical compounds as semiconductors and luminescent materials [1,2,3]
We have examined the conditions for C–H borylation of unsubstituted HBC
We attempted the iridium catalyst and reagents that we have reported as the suitable C–H borylation conditions for warped nanographene: [Ir(OMe)cod]2, 3,4,7,8-tetramethyl1,10-phenanthroline, HBpin (Bpin: 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) and cyclopentyl methyl ether (CPME) [21]
Summary
Polycyclic aromatic hydrocarbons (PAHs) are beneficial chemical compounds as semiconductors and luminescent materials [1,2,3]. We have established suitable reaction conditions for the synthesis of hexaborylated HBC 1. The structure of -obtained 1 was confirmed by X-ray crystallography, and the electronic effects of the boryl groups were investigated through optoelectronic measurements and density functional theory (DFT) calculations.
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