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Novel reactions of a neutral organic reductant : reductive coupling and nanoparticle synthesis

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dc.contributor.advisor Timothy M. Swager. en_US Mork, Anna Jolene en_US
dc.contributor.other Massachusetts Institute of Technology. Dept. of Chemistry. en_US 2012-09-27T18:12:05Z 2012-09-27T18:12:05Z 2012 en_US 2012 en_US
dc.description Thesis (S.M.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2012. en_US
dc.description Vita. Cataloged from PDF version of thesis. en_US
dc.description Includes bibliographical references (p. 53-55). en_US
dc.description.abstract A recently developed bis-pyridinylidene neutral organic electron donor captured our interest as a potential source of new chemistries for reductive coupling and the synthesis of group IV nanoparticles. This super electron donor was used as a co-reductant for nickel-catalyzed reductive coupling of aryl halides in order for the reaction to be homogeneous and avoid the traditional co-reductant, zinc, previously reported for these Yamamoto-type dehalogenative couplings. Reductive coupling was somewhat successful for specific substrates, including 4- bromoanisole and 2,5-dibromothiophene, but competing hydrodehalogenation of the aryl halide was problematic for both expanding the substrate scope and increasing the length of the polymers generated from this reaction. The attempt to synthesize silicon and germanium nanoparticles from reduction of the corresponding tetrachloride precursors using this super organic electron donor met limited success. Dimerization of silicon species occurred, but there was little conclusive evidence of nanoparticle formation. Finally, in a brief side-project to explore other applications of the organic reductant, the molecule was shown to successfully n-dope both p-type and n-type organic electronic materials. en_US
dc.description.statementofresponsibility by Anna Jolene Mork. en_US
dc.format.extent 63 p. en_US
dc.language.iso eng en_US
dc.publisher Massachusetts Institute of Technology en_US
dc.rights M.I.T. theses are protected by copyright. They may be viewed from this source for any purpose, but reproduction or distribution in any format is prohibited without written permission. See provided URL for inquiries about permission. en_US
dc.rights.uri en_US
dc.subject Chemistry. en_US
dc.title Novel reactions of a neutral organic reductant : reductive coupling and nanoparticle synthesis en_US
dc.type Thesis en_US S.M. en_US
dc.contributor.department Massachusetts Institute of Technology. Dept. of Chemistry. en_US
dc.identifier.oclc 809940951 en_US

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