The Nagoya University of Japan announced on August 5, 2016 that it has developed a new method for easily synthesizing "organic nanotubes" in a tubular structure with carbon nanotubes based on organic molecules using a simple organic compound in two steps. The use of different designs for the skeleton of organic nanotubes can impart semiconductor properties, electrical conductivity, molecular recognition, molecular attraction, and other functions, and therefore it is expected to be widely used as a functional material.

Organic nanotubes (ONT: Organic Nanotube) have nano-sized cylindrical pores, which are expected to be used for molecular recognition of materials, ion channels of biological membranes, and conductive materials due to its conductivity and luminescence characteristics. However, the organic nanotubes that have been released so far have the problem of structural fragility, because they maintain the tube structure under weak interactions such as hydrogen bonds and aromatic ring π-π interactions.

If we can synthesize "covalent ONT" that covalently bonds the entire tube structure like carbon nanotubes, we can develop harder and stronger organic nanotubes, and we hope to increase them. Conductive and optical properties. However, it is very difficult to synthesize organic nanotubes with cross-linked covalent bonds. There is no clear synthesis method.

The researchers at Nagoya University used a small organic molecule to synthesize a helical polymer to generate a photocrosslinking reaction within the backbone of a helical polymer, and developed a "helix-to-tube method for the simple synthesis of covalently-stimulated organic nanotubes." ". Spiral polymers are designed and synthesized from two polyacetylene acetylene (poly-PDE) polymers with two acetylene backbones connected at the meta position of the benzene ring.

The specific molecular design is to introduce an amide group that promotes helix formation using hydrogen bonds in the side chain of poly-PDE, an oligomeric glycol chain that increases solubility in an organic solvent, and asymmetry that stimulates chiral helix formation. The carbon center makes it spontaneously spiral. Next, the helical poly-PDE is irradiated with light using a mercury lamp or the like to form a cross-linked covalent bond, thereby constructing a covalent ONT. This reaction is a type of topological chemical polymerization caused by the irradiation of diacetylene molecules in solid crystals.

The results of Raman spectroscopic analysis and ultraviolet visual absorption measurement of the synthesized covalent ONT show that a crosslinked conjugated ene acetylene structure in which the entire helical polymer has a strong bond is indeed formed. Also confirmed by transmission electron microscopy, the synthesized covalent ONT is a covalently bonded organic nanotubular structure. In the future, by embedding a variety of aromatic ring components, it is also expected to develop covalent organic nanotubes having various diameters and functions.

The results of this study were published on the online newsletter of the Journal of the American Chemical Society, American Journal of Chemicals, on August 4, 2016 (US Eastern Time). (Special Contributor: Kudosuke)

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