Issue 8, 2013

Bottom-up synthesis and structures of π-lengthened tubular macrocycles

Abstract

Belt-persistent tubular cycloarylenes possessing extended sp2-networks of finite single-wall carbon nanotubes (SWNT) have been synthesised from an abundantly available pigment possessing the dibenzo[def,mno]chrysene (anthanthrene) framework. The introduction of bulky substituents allowed for the diastereoselective production of a single helical isomer as a racemate, and the extension of the π-systems in the cycloarylene unexpectedly lowered the enthalpic barrier for the rotation of the arylene unit. Crystallographic analysis of the helical finite SWNT molecules revealed alternate layers of homohelical columns.

Graphical abstract: Bottom-up synthesis and structures of π-lengthened tubular macrocycles

Supplementary files

Article information

Article type
Edge Article
Submitted
08 Mar 2013
Accepted
19 May 2013
First published
21 May 2013

Chem. Sci., 2013,4, 3179-3183

Bottom-up synthesis and structures of π-lengthened tubular macrocycles

T. Matsuno, S. Kamata, S. Hitosugi and H. Isobe, Chem. Sci., 2013, 4, 3179 DOI: 10.1039/C3SC50645B

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