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dc.contributor.advisor Tour, James M.
dc.creatorEngel, Aaron S.
dc.date.accessioned 2009-06-04T08:44:38Z
dc.date.available 2009-06-04T08:44:38Z
dc.date.issued 2002
dc.identifier.urihttps://hdl.handle.net/1911/17504
dc.description.abstract Several fully conjugated organic molecules incorporating 2,7-difunctionalized pyrenes, 2,7-difunctionalized phenanthrenes, 2,5-difunctionalized pyrimidines and 5-functionalized pyrimidines have been synthesized. These molecules all feature a protected thiophenol terminus which under suitable deprotection conditions liberates the free thiol permitting for their self-assembly in the presence of a clean gold surface. This thesis features an improved synthesis of 2,7-dibromopyrene via an optimized hydrogenation/nitration/separation procedure. In addition, a novel route to 2,7-dibromophenanthrene is presented which begins with an easy bromination of diphenic acid and culminates in a hydrazine-induced cyclization of the corresponding 2,2'-dicarbaldehyde to give the desired product dibromophenanthrene in high yield. The completed device syntheses feature various palladium-catalyzed coupling methods to afford the appropriate arylene-ethynlene systems and these will be presented.
dc.format.extent 255 p.
dc.format.mimetype application/pdf
dc.language.iso eng
dc.subjectOrganic chemistry
dc.title Synthesis of pyrene, phenanthrene and pyrimidine device candidates for use in molecular electronics
dc.type.genre Thesis
dc.type.material Text
thesis.degree.department Chemistry
thesis.degree.discipline Natural Sciences
thesis.degree.grantor Rice University
thesis.degree.level Masters
thesis.degree.name Master of Science
dc.identifier.citation Engel, Aaron S.. "Synthesis of pyrene, phenanthrene and pyrimidine device candidates for use in molecular electronics." (2002) Master’s Thesis, Rice University. https://hdl.handle.net/1911/17504.


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