A Large π-Extended Carbon Nanoring Based on Nanographene Units: Bottom-Up Synthesis, Photophysical Properties, and Selective Complexation with Fullerene C70

Dapeng Lu; Guilin Zhuang; Haotian Wu; Song Wang; Shangfeng Yang; Pingwu Du

doi:10.1002/anie.201608963

A Large π-Extended Carbon Nanoring Based on Nanographene Units: Bottom-Up Synthesis, Photophysical Properties, and Selective Complexation with Fullerene C₇₀

Angew Chem Int Ed Engl. 2017 Jan 2;56(1):158-162. doi: 10.1002/anie.201608963. Epub 2016 Dec 2.

Authors

Dapeng Lu¹, Guilin Zhuang², Haotian Wu¹, Song Wang¹, Shangfeng Yang¹, Pingwu Du¹

Affiliations

¹ CAS Key Laboratory of Materials for Energy Conversion, Department of Materials Science and Engineering, Collaborative Innovation Center of Chemistry for Energy Materials (iChEM), University of Science and Technology of China (USTC), Hefei, 230026, P.R. China.
² College of Chemical Engineering, Zhejiang University of Technology, 18, Chaowang Road, Hangzhou, Zhejiang Province, 310032, China.

PMID: 27910250
DOI: 10.1002/anie.201608963

Abstract

Herein we report the organoplatinum-mediated bottom-up synthesis, characterization, and properties of a novel large π-extended carbon nanoring based on a nanographene hexa-peri-hexabenzocoronene (HBC) building unit. This tubular structure can be considered as an example of the longitudinal extension of the cycloparaphenylene scaffold to form a large π-extended carbon nanotube (CNT) segment. The cyclic tetramer of a tetramesityl HBC ([4]CHBC) was synthesized by the reaction of a 2,11-diborylated hexa-peri-hexabenzocoronene with a platinum complex, followed by reductive elimination. The structure of this tubular molecule was further confirmed by physical characterization. Theoretical calculations indicate that the strain energy of this nanoring is as high as 49.18 kcal mol^-1 . The selective supramolecular host-guest interaction between [4]CHBC and C₇₀ was also investigated.

Keywords: carbon nanorings; carbon nanotubes; fullerenes; host-guest systems; π conjugation.

Publication types

Research Support, Non-U.S. Gov't