A Practical Synthesis of Bridged Diarylacetylenes

Authors

Ruchi Shukla, Marquette University
Daniel M. Brody, Marquette University
Sergey V. Lindeman, Marquette UniversityFollow
Rajendra Rathore, Marquette University

Document Type

Article

Language

eng

Publication Date

2006

Publisher

American Chemical Society

Source Publication

The Journal of Organic Chemistry

Source ISSN

0022-3263

Abstract

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.

Comments

Accepted version. The Journal of Organic Chemistry, Vol. 71, No. 16 (2006): 6124-6129. DOI. © 2006 American Chemical Society. Used with permission.

Recommended Citation

Shukla, Ruchi; Brody, Daniel M.; Lindeman, Sergey V.; and Rathore, Rajendra, "A Practical Synthesis of Bridged Diarylacetylenes" (2006). Chemistry Faculty Research and Publications. 647.
https://epublications.marquette.edu/chem_fac/647