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

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• 作者：Kaho Maeda ; Liu Hong ; Taishi Nishihara ; Yusuke Nakanishi ; Yuhei Miyauchi ; Ryo Kitaura ; Naoki Ousaka ; Eiji Yashima ; Hideto Ito ; Kenichiro Itami
• 刊名：Journal of the American Chemical Society
• 出版年：2016
• 出版时间：August 31, 2016
• 年：2016
• 卷：138
• 期：34
• 页码：11001-11008
• 全文大小：717K
• 年卷期：0
• ISSN：1520-5126

文摘

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.