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Advances in gold-carbon bond formation: mono-, di-, and triaurated organometallics

Heckler, James E
http://rave.ohiolink.edu/etdc/view?acc_num=case1441363597

Abstract Details

2016, Doctor of Philosophy, Case Western Reserve University, Chemistry.
Novel auration methods have been developed and used to synthesize new compounds featuring up to three (phosphine)- or (N-heterocyclic carbene)gold(I) fragments bound to aromatic cycles. This has direct implications on the photophysics of fluorescent molecules—the heavy atom effect of gold can unlock longer-lived phosphorescence, of interest in light emitting devices. Gold also affects absorption properties of molecules of relevance to organic photovoltaics. New compounds described herein are produced by transmetalation conditions from boronic acids in divergent pathways—transmetalations of gold halides, in the presence of base, yield monogold compounds, whereas gold sources featuring weakly nucleophilic anions are competent diauration agents. A gold-gold aurophilic interaction supports geminal diauration. In copper-catalyzed reactions of gold alkynyls and azides, new gold triazolyls are for the first time synthesized in aqueous mixtures; air- and moisture-free conditions are avoided. These compounds are composed of molecular motifs that are of relevance to medicine. All isolated products are characterized; spectroscopic, photophysical, structural, and theoretical data are obtained and discussed.
Carlos Crespo-Hernández, Ph.D. (Committee Chair)
Anthony Pearson, Ph.D. (Committee Member)
Geneviève Sauvé, Ph.D. (Committee Member)
Horst von Recum, Ph.D. (Committee Member)
Thomas Gray, Ph.D. (Advisor)
252 p.
Chemistry; Inorganic Chemistry; Organic Chemistry
gold; transmetalation; cycloaddition; geminal diauration; copper; fluorescence; phosphorescence; heavy atom effect; click chemistry; relativistic effects; triazole; arylboronic acids; alkynyls; azides; DFT; N-heterocyclic carbene; phosphine; aurophilicity

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Citations

  • Heckler, J. E. (2016). Advances in gold-carbon bond formation: mono-, di-, and triaurated organometallics [Doctoral dissertation, Case Western Reserve University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=case1441363597

    APA Style (7th edition)

  • Heckler, James. Advances in gold-carbon bond formation: mono-, di-, and triaurated organometallics. 2016. Case Western Reserve University, Doctoral dissertation. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=case1441363597.

    MLA Style (8th edition)

  • Heckler, James. "Advances in gold-carbon bond formation: mono-, di-, and triaurated organometallics." Doctoral dissertation, Case Western Reserve University, 2016. http://rave.ohiolink.edu/etdc/view?acc_num=case1441363597

    Chicago Manual of Style (17th edition)

case1441363597
585
© 2015, all rights reserved.
This open access ETD is published by Case Western Reserve University School of Graduate Studies and OhioLINK.