Synthesis of Giant π-Extended Molecular Macrocyclic Rings as Finite Models of Carbon Nanotubes Displaying Enriched Size-Dependent Physical Properties

Hongxing Jia; Guilin Zhuang; Qiang Huang; Jinyi Wang; Yayu Wu; Shengsheng Cui; Shangfeng Yang; Pingwu Du

doi:10.1002/chem.201905396

Synthesis of Giant π-Extended Molecular Macrocyclic Rings as Finite Models of Carbon Nanotubes Displaying Enriched Size-Dependent Physical Properties

Chemistry. 2020 Feb 17;26(10):2159-2163. doi: 10.1002/chem.201905396. Epub 2020 Jan 31.

Authors

Hongxing Jia¹, Guilin Zhuang², Qiang Huang¹, Jinyi Wang¹, Yayu Wu¹, Shengsheng Cui¹, Shangfeng Yang¹, Pingwu Du¹

Affiliations

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

PMID: 31840850
DOI: 10.1002/chem.201905396

Abstract

Bottom-up synthesis of π-extended macrocyclic carbon rings is promising for constructing length- and diameter-specific carbon nanotubes (CNTs). However, it is still a great challenge to realize size-controllable giant carbon macrocycles. Herein, a tunable synthesis of curved nanographene-based giant π-extended macrocyclic rings (CHBC[n]s; n=8, 6, 4), as finite models of armchair CNTs, is reported. Among them, CHBC[8] contains 336 all-carbon atoms and is the largest cyclic conjugated molecular CNT segment ever reported. CHBC[n]s were systematically characterized by various spectroscopic methods and applied in photoelectrochemical cells for the first time. This revealed that the proton chemical shifts, fluorescence, and electronic and photoelectrical properties of CHBC[n]s are highly dependent on the macrocycle diameter. The tunable bottom-up synthesis of giant macrocyclic rings could pave the way towards large π-extended diameter- and chirality-specific CNT segments.

Keywords: carbon; cyclization; macrocycles; nanotubes; photophysics.

Abstract

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