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Construction of Covalent Organic Nanotubes by Light-Induced Cross-Linking of Diacetylene-Based Helical Polymers

Kaho Maeda, Liu Hong, Taishi Nishihara, Yusuke Nakanishi, Yuhei Miyauchi, Ryo Kitaura, Naoki Ousaka, Eiji Yashima, Hideto Ito,* and Kenichiro Itami*

J. Am. Chem. Soc. 2016138, 11001–11008. DOI: 10.1021/jacs.6b05582 

Journal of the American Chemical Society

 Organic nanotubes (ONTs) are tubular nanostructures composed of small molecules or macromolecules that have found various applications including ion sensor/channels, gas absorption, and photovoltaics. While most ONTs are constructed by self-assembly processes based on weak noncovalent interactions, this unique property gives rise to the inherent instability of their tubular structures. Herein, we report a simple “helix-to-tube” strategy to construct robust, covalent ONTs from easily accessible poly(m-phenylene diethynylene)s (poly-PDEs) possessing chiral amide side chains that can adopt a helical conformation through hydrogen-bonding interactions. The helically folded poly-PDEs subsequently undergo light-induced cross-linking at longitudinally aligned 1,3-butadiyne moieties across the whole helix to form covalent tubes (ONTs) both in solution and solid phases. The structures of poly-PDEs and covalent ONTs were characterized by spectroscopic analyses, diffraction analysis, and microscopic analyses. We envisage that this simple yet powerful “helix-to-tube” strategy will generate a range of ONT-based materials by introducing functional moieties into a monomer.

[press release(JP)][press release(EN)]

Selected as the cover art in J. Am. Chem. Soc. 2016, vol.138, issue 38
Highlighted in JACS SPOTLIGHTS (J. Am. Chem. Soc. 2016, 138, 10717. DOI: 10.1021/jacs.6b08657)
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