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Synthesis and Spectroscopy of Cofacial Distilbenes and Aggregated 9-Substituted Anthracenes

Wongwitwichote, Wongwit

Abstract Details

2010, Doctor of Philosophy, University of Akron, Chemistry.
In recent years, π-conjugated macromolecules and self-assembled complexes have attracted the attention of researchers for both their novel properties and as alternative materials to classical semiconductor-based devices. Interchain interactions between π-conjugated molecules can potentially influence the electronic and optical performance of organic photovoltaic devices. First, the synthesis and preliminary photophysical properties of bridged-cofacial stilbenes and oligo(phenylene vinylene) compounds was performed. In this work, a series of symmetric stilbenes and oligo(phenylenevinylene) bridged by either xanthene or dibenzofuran was prepared. The cofacial dimers of the stilbene derivatives showed excitonic coupling between the stilbene chains, whereas, the cofacial dimers of oligo(phenylenevinylene) derivatives did not show excitonic coupling due to the more stable excited state localized on the oligo(phenylenevinylene) group compared to the stilbene derivatives. Second, the synthesis of a dimeric oligo(phenyleneethynylene) (OPE) complex utilizing hydrogen bonding from glycoluril groups was attempted in order to investigate the effects of the long-range interchain interactions of π-conjugated materials. However, the low solubility of the intermediate compounds made the project difficult to accomplish. Finally, the synthesis of trialkoxybenzoyl substituted 9-anthracenes was performed in order to study the effect of emission induced by aggregation caused by π- conjugated materials. The emission spectra indicated excimer formation in these trialkoxybenzoyl substituted 9-anthracenes that was attributed to the π-π stacking interactions in the excited states of these compound
David Modarelli, Dr. (Advisor)
Michael Taschner, PhD (Committee Member)
Chrys Wesdemiotis, PhD (Committee Member)
Matthew Espe, PhD (Committee Member)
Teresa Cutright, PhD (Committee Member)
126 p.

Recommended Citations

Citations

  • Wongwitwichote, W. (2010). Synthesis and Spectroscopy of Cofacial Distilbenes and Aggregated 9-Substituted Anthracenes [Doctoral dissertation, University of Akron]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=akron1285256001

    APA Style (7th edition)

  • Wongwitwichote, Wongwit. Synthesis and Spectroscopy of Cofacial Distilbenes and Aggregated 9-Substituted Anthracenes. 2010. University of Akron, Doctoral dissertation. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=akron1285256001.

    MLA Style (8th edition)

  • Wongwitwichote, Wongwit. "Synthesis and Spectroscopy of Cofacial Distilbenes and Aggregated 9-Substituted Anthracenes." Doctoral dissertation, University of Akron, 2010. http://rave.ohiolink.edu/etdc/view?acc_num=akron1285256001

    Chicago Manual of Style (17th edition)