Persistent Link:
http://hdl.handle.net/10150/280487
Title:
Synthesis and characterization of octasubstituted phthalocyanines
Author:
Minch, Britt Austin
Issue Date:
2004
Publisher:
The University of Arizona.
Rights:
Copyright © is held by the author. Digital access to this material is made possible by the University Libraries, University of Arizona. Further transmission, reproduction or presentation (such as public display or performance) of protected items is prohibited except with permission of the author.
Abstract:
Substituted phthalocyanines (Pcs) have been studied intensely for decades as pigments because of their high molar absorptivities, thermal stability, and stability towards light exposure. These materials also show promise as electron and hole transport layers in a variety of device applications such as organic field effect transistors and photovoltaics. This dissertation describes the synthesis of several new phthalocyanines (Pcs) and the fabrication of highly ordered supramolecular assemblies. Efforts to increase the coherence of Pc assemblies have included the incorporation of side chains containing polymerizable and hydrogen bonding moieties. The synthesis of 2,3,9,10,16,17,23,24-octa thioether substituted Pcs was designed to allow the incorporation of diverse thioether side chains. The synthesis is shorter and uses milder conditions than the previous synthetic methods explored in the O'Brien and Armstrong groups. Serendipitously, the thioether linkage allow for chalcogen-chalcogen interactions, increasing the attraction of the Pcs sufficiently to provide for crystal growth. The order of the supramolecular materials has been examined in thin films as well as in solution. The UV-Visible and IR spectroscopic data, Langmuir-Blodgett (LB) film forming behavior, thermotropic properties, and photovoltaic properties are reported for each Pc derivative prepared. Although each compound prepared displays some degree of order, the degree to of this order is controlled by the nature of the side chain. The Pcs exhibit long range ordering on a macroscopic level, as can be seen from polarized optical microscopy, atomic force microscopy, IR, and X-ray diffraction techniques.
Type:
text; Dissertation-Reproduction (electronic)
Keywords:
Chemistry, Organic.
Degree Name:
Ph.D.
Degree Level:
doctoral
Degree Program:
Graduate College; Chemistry
Degree Grantor:
University of Arizona
Advisor:
Armstrong, Neal R.

Full metadata record

DC FieldValue Language
dc.language.isoen_USen_US
dc.titleSynthesis and characterization of octasubstituted phthalocyaninesen_US
dc.creatorMinch, Britt Austinen_US
dc.contributor.authorMinch, Britt Austinen_US
dc.date.issued2004en_US
dc.publisherThe University of Arizona.en_US
dc.rightsCopyright © is held by the author. Digital access to this material is made possible by the University Libraries, University of Arizona. Further transmission, reproduction or presentation (such as public display or performance) of protected items is prohibited except with permission of the author.en_US
dc.description.abstractSubstituted phthalocyanines (Pcs) have been studied intensely for decades as pigments because of their high molar absorptivities, thermal stability, and stability towards light exposure. These materials also show promise as electron and hole transport layers in a variety of device applications such as organic field effect transistors and photovoltaics. This dissertation describes the synthesis of several new phthalocyanines (Pcs) and the fabrication of highly ordered supramolecular assemblies. Efforts to increase the coherence of Pc assemblies have included the incorporation of side chains containing polymerizable and hydrogen bonding moieties. The synthesis of 2,3,9,10,16,17,23,24-octa thioether substituted Pcs was designed to allow the incorporation of diverse thioether side chains. The synthesis is shorter and uses milder conditions than the previous synthetic methods explored in the O'Brien and Armstrong groups. Serendipitously, the thioether linkage allow for chalcogen-chalcogen interactions, increasing the attraction of the Pcs sufficiently to provide for crystal growth. The order of the supramolecular materials has been examined in thin films as well as in solution. The UV-Visible and IR spectroscopic data, Langmuir-Blodgett (LB) film forming behavior, thermotropic properties, and photovoltaic properties are reported for each Pc derivative prepared. Although each compound prepared displays some degree of order, the degree to of this order is controlled by the nature of the side chain. The Pcs exhibit long range ordering on a macroscopic level, as can be seen from polarized optical microscopy, atomic force microscopy, IR, and X-ray diffraction techniques.en_US
dc.typetexten_US
dc.typeDissertation-Reproduction (electronic)en_US
dc.subjectChemistry, Organic.en_US
thesis.degree.namePh.D.en_US
thesis.degree.leveldoctoralen_US
thesis.degree.disciplineGraduate Collegeen_US
thesis.degree.disciplineChemistryen_US
thesis.degree.grantorUniversity of Arizonaen_US
dc.contributor.advisorArmstrong, Neal R.en_US
dc.identifier.proquest3119968en_US
dc.identifier.bibrecord.b45645371en_US
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