Synthesis, Properties, and Intermolecular Interactions in the Solid States of π-Congested X-Shaped 1,2,4,5-Tetra(9-anthryl)benzenes

A Negishi coupling based synthesis of 1,2,4,5-tetra(9-anthryl)benzene derivatives, possessing X-shaped molecular structures, is described. The results X-ray crystallographic analysis show that two-dimensional highly ordered packing structure the crystalline state unsubstituted derivative a consequence intermolecular π-π and CH-π interactions between anthracene units. Photoirradiation as precipitated solution promotes intramolecular [4+4] photocycloaddition reactions both adjacent pairs units to produce polycyclic product having unique 1.700 Å long carbon-carbon single bond. Furthermore, charge-transfer complexes, displaying near-infrared absorption emission, are generated by co-crystallization member group with electron-acceptor molecules.