Noncentrosymmetric Packings Influenced by Electronic Properties of Products of Click Reactions.

Though 1,4-disubstituted 1,2,3-triazole rings have been utilized as electronic bridges in the soln. phase, the use of a triazole ring to serve as an electronic bridge of small mols. in the cryst. state has been underdeveloped. Here two compds. with a central 1,4-disubstituted 1,2,3-triazole ring are synthesized to investigate the electronic bridging between terminal stilbazole and pyridine groups in the cryst. phase. The electronic properties of the mols. are characterized through soln. phase UV-vis spectroscopy, single crystal X-ray diffractions, and d.-of-state and gas-phase DFT calcns. We show that the electronic bridging behavior of a 1,4-disubstituted 1,2,3-triazole ring derived from a click reaction is maintained in the solid state by rare head-to-head (hh) packing in noncentrosym. crystal environments. [on SciFinder(R)]