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.

本研究采用高产率（经典）合成方法与易得起始原料，成功实现了多克级规模的桥联二芳基乙炔（bridged diarylacetylenes）高效实用合成。通过X射线晶体学（X-ray crystallography）对代表性桥联二芳基乙炔进行的结构分析表明，各类桥联二芳基乙炔的构象、线性三键的弯曲程度以及芳环平均平面间的夹角，均受芳环与醚基（ethereal groups）之间的p-π共轭（p−π conjugation）作用调控。此外，该合成路线还可制备适位溴取代桥联二芳基乙炔，此类化合物未来有望用于合成聚合物类似物，以及六芳基苯衍生物（hexaarylbenzene derivatives），后者可应用于新兴的分子电子学（molecular electronics）与纳米技术（nanotechnology）领域。