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dc.contributor.authorHein, Samuel Jay
dc.date.accessioned2017-07-07T12:48:40Z
dc.date.available2017-07-07T12:48:40Z
dc.date.issued2017-05-30
dc.identifier.otherHein_cornellgrad_0058F_10304
dc.identifier.otherhttp://dissertations.umi.com/cornellgrad:10304
dc.identifier.otherbibid: 9948840
dc.identifier.urihttps://hdl.handle.net/1813/51617
dc.description.abstractThis dissertation describes recent advances in methodology to access novel aromatic architectures using a benzannulation strategy (Chapter 1). Silyl protected acetylenes are readily reacted to yield the corresponding 2-naphthylsilane. These compounds serve as synthetically useful building blocks for further derivatization and iterative benzannulation to access sterically crowded substrates (Chapter 2). Despite the high efficiency of this reaction, phenylene ethynylene macrocycles prove to be too rigid to undergo complete benzannulation (Chapter 3). Finally, the scope of this transformation was expanded beyond aryl substituted acetylenes with the benzannulation of silyl-haloacetylenes (Chapter 4). These products readily generate 2-naphthynes with the addition of cesium fluoride and can be oligomerized or cyclized to isolate substituted ortho-naphthalenes. Through our fundamental studies into this transformation, we have shown it serves as a versatile reaction in the organic synthetic chemists toolbox to access novel aromatic architectures.
dc.language.isoen_US
dc.subjectaromatic
dc.subjectGraphene
dc.subjectorganic
dc.subjectBenzannulation
dc.subjectPAH
dc.subjectPolymer
dc.subjectOrganic chemistry
dc.titleThe Synthesis of Naphthalene-Containing Compounds and Materials Using Benzannulation Reactions
dc.typedissertation or thesis
thesis.degree.disciplineChemistry and Chemical Biology
thesis.degree.grantorCornell University
thesis.degree.levelDoctor of Philosophy
thesis.degree.namePh. D., Chemistry and Chemical Biology
dc.contributor.chairDichtel, William R
dc.contributor.committeeMemberCoates, Geoff
dc.contributor.committeeMemberOber, Christopher K
dcterms.licensehttps://hdl.handle.net/1813/59810
dc.identifier.doihttps://doi.org/10.7298/X46D5R3M


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