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Issue 8, 2013
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Bottom-up synthesis and structures of π-lengthened tubular macrocycles

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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

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Publication details

The article was received on 08 Mar 2013, accepted on 19 May 2013 and first published on 21 May 2013


Article type: Edge Article
DOI: 10.1039/C3SC50645B
Citation: Chem. Sci., 2013,4, 3179-3183
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    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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