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

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journal contribution
posted on 03.08.2016 by Kaho Maeda, Liu Hong, Taishi Nishihara, Yusuke Nakanishi, Yuhei Miyauchi, Ryo Kitaura, Naoki Ousaka, Eiji Yashima, Hideto Ito, Kenichiro Itami
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.