Supramolecular Construction of a Highly Elongated π-Conjugated Structure in the Solid State: Metal-Free Click Reaction Guided by C-H Hydrogen Bonding

A planned topochemical azide-alkyne cycloaddition is developed in the organic solid state to generate a highly elongated π-conjugated 1,2,3-triazole by a metal-free click reaction. The triazole is generated using a binary cocrystal composed of stilbenes that are covalently adjoined in a single-crystal-to-single-crystal transformation. The click reaction is accompanied by a large-scale structural reorganization involving procession-like movements of 1D stacked columns into a 2D layered structure. The formation of the layered structure is guided by newly formed triazoles self-assembling via C-H···N hydrogen bonding.