Intramolecular [2 + 2] Photodimerization Achieved in the Solid State via Coordination-Driven Self-Assembly.

An intramolecular [2 + 2] photocycloaddition is achieved in the organic solid state via self-assembly of Ag(I) ions and an endo-ditopic bipyridine. The cations aide to organize carbon-carbon double (C═C) bonds attached to the bipyridine for the cycloaddition reaction. The C═C bonds react regioselectively and quantitatively to afford a photoproduct with edge-sharing four-, five-, and six-membered rings.

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 solution phase, the use of a triazole ring to serve as an electronic bridge of small molecules in the crystalline state has been underdeveloped. Here two compounds 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 crystalline phase. The electronic properties of the molecules are characterized through solution phase UV-vis spectroscopy, single crystal X-ray diffractions, and density-of-state and gas-phase DFT calculations.