A Practical Synthesis of Bridged Diarylacetylenes

An efficient and practical synthesis of bridged diarylacetylenes in multigram quantities has been
successfully carried out using high-yielding (classical) synthetic methods and readily available starting
materials. The structural analysis of the representative bridged diarylacetylenes by X-ray crystallography
strongly suggests that conformations, bending of the linear triple bond, and the angle between the mean
planes of aromatic rings in various bridged diarylacetylenes are governed by the p−π conjugation among
the aromatic rings and the ethereal groups. Furthermore, the synthetic scheme also allows the preparation
of (appropriately) bromo-substituted bridged diarylacetylenes which hold potential for their future usage
for the preparation of polymeric analogues as well as the hexaarylbenzene derivatives for potential
applications in the emerging area of molecular electronics and nanotechnology.