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

Taisuke Matsuno; Sho Kamata; Shunpei Hitosugi; Hiroyuki Isobe

doi:10.1039/c3sc50645b

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

Taisuke Matsuno, Sho Kamata, Shunpei Hitosugi, Hiroyuki Isobe

SCI - Chemistry

Research output: Contribution to journal › Article › peer-review

105 Citations (Scopus)

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.

Original language	English
Pages (from-to)	3179-3183
Number of pages	5
Journal	Chemical Science
Volume	4
Issue number	8
DOIs	https://doi.org/10.1039/c3sc50645b
Publication status	Published - 2013 Jul 1

ASJC Scopus subject areas

Chemistry(all)

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N2 - 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.

AB - 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.

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

Abstract

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