Topochemical polymerization of macrocyclic diacetylene with a naphthalene moiety for a tubular-shaped polydiacetylene chromophore

Abstract

Tubular-shaped chromophores have great potential in chemical and material sciences. A naphthalene-containing macrocyclic diacetylene (MCDA-Naph) was synthesized to access covalently linked organic nanotubes (ONTs) through topochemical polymerization. Single crystal X-ray analysis revealed that MCDA-Naph adopts the desired tubular array with favorable molecular orientation. UV irradiation of the molecularly stacked MCDA-Naph resulted in 1,4-addition polymerization and the generation of conjugated ene-yne chromophores. Density functional theory (DFT) provided evidence for tubular polydiacetylene nanotubes. © 2018