Date of Award
Master of Science
A variety of symmetric, π-conjugated organic chromophores were synthesized using trans-benzobis(oxazole) as an acceptor and the core of dye, changing the donating moieties in the 2- and 6-positions. The optical and electrical properties of these compounds were investigated for potential use in organic electronic devices, and these compounds exhibited relatively narrow band-gaps, which were tuned by changing the donating group present. Additionally, a significant solvatochromatic effect was noted for some of the dyes. Synthetic routes towards asymmetric chromophores using benzobis(oxazole)s as a π-spacer between an electron-acceptor and donor were also developed, using the orthoester condensation and an intramolecular Beckmann rearrangement as orthogonal oxazole ring-closing methods. To broaden the availability of conjugated compounds for use in the orthoester condensation, significant progress was also made on the synthesis of previously unknown orthoesters.
James Scott Klimavicz
Klimavicz, James Scott, "Synthesis of donor-acceptor benzobis(oxazole) small molecules" (2013). Graduate Theses and Dissertations. 13376.