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