Date of Award

1-1-2013

Language

English

Document Type

Master's Thesis

Degree Name

Master of Science (MS)

College/School/Department

Department of Chemistry

Content Description

1 online resource (vii, 70 pages) : illustrations (some color)

Dissertation/Thesis Chair

Eric Block

Committee Members

Paul Toscano

Keywords

Buckminsterfullerene, Polycyclic aromatic hydrocarbons, Heterocyclic compounds, Thiophenes

Subject Categories

Organic Chemistry

Abstract

Thiacorannulene is an unknown, open geodesic heteropolyarene comprised of a central five-membered ring surrounded by four benzene rings and one thiophene ring. This heterobuckybowl is expected to have unique physical, chemical and biological properties. The curvature in thiacorannulene should provide two distinct surfaces, convex and concave, and should affect properties such as dipole moment, ionization potential, metal binding, etc. Having a thiophene ring embedded in its structure is expected to influence the reactivity of this compound. We sought to devise syntheses of the unknown heterobuckybowl based on earlier, optimized syntheses of buckybowls, heterobuckybowls, and heterocirculenes. Details of our attempted syntheses of thiacorannulene will be presented.

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