Preparing Nanotubes via Polymerization of Diacetylene Functionality Containing Carbon-based Macrocycles

Abstract

Nanofibers and nanotubes have been extensively studied in materials science due to their extraordinary thermal conductivity, excellent mechanical and electrical properties, and their potential capability for gas storage. Their potential applications at the forefront of technology areas have attracted people’s attention. Diacetylene functionality containing macrocycles with different frameworks have been designed and synthesized. (S)-BINOL-based building block macrocyclic ether 2.4, macrocyclic ester 2.9a and amide 2.9b have been synthesized. A single crystal was obtained for 2.9b from a THF-hexanes solvent system and X-ray data was collected while the other macrocycle 2.9a furnished gels. X-ray crystallography demonstrated that macrocycle 2.9b does not stack face-to-face, due to steric hindrance. Planar macrocycles with carbazole and dibenzofuran as flat backbone to minimize steric hindrance have also been designed, which may increase the possibility to obtain a state of supramolecular stacking, and synthesis of some of the proposed structures was attempted. Carbazole-based tetramer building block macrocycles 3.6 (side chain free) and 3.16 (alkylated) have been successfully synthesized and characterized.