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Synthesis 2019; 51(24): 4576-4581
DOI: 10.1055/s-0039-1690206
DOI: 10.1055/s-0039-1690206
paper
Sumanene Hexaester: An Electron-Deficient Buckybowl
This work was supported by a Grant-in-Aid for Scientific Research on Innovative Areas ‘π-Figuration’ (no. 26102002 for H.S. and no. 26102008 for T.F.) and ‘Dynamic Alliance for Open Innovation Bridging Human, Environment and Materials’ from the Ministry of Education, Culture, Sports, Science and Technology (MEXT).Further Information
Publication History
Received: 19 August 2019
Accepted after revision: 12 September 2019
Publication Date:
30 September 2019 (online)


Abstract
2,3,5,6,8,9-Hexakis(phenoxycarbonyl)sumanene, a hexasubstituted sumanene with CO2Ph groups at the peripheral aromatic carbons, was successfully prepared in good yield by Pd-catalyzed phenoxycarbonylation using a solvent of phenyl formate. Single-crystal X-ray structural analysis of this compound revealed the formation of a one-dimensional columnar structure, stacked in a staggered manner. The UV and emission spectra of this showed clear red-shifts compared with those of pristine sumanene, indicating the extension of the conjugation system.
Key words
sumanene - buckybowls - palladium catalysis - phenoxycarbonylation - electron-deficient polycyclic aromatic hydrocarbons - columnar packing structureSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690206.
- Supporting Information