Synthesis and characterization of new octasubstituted phthalocyanines: Supramolecular materials for thin film electronic, optical and chemical sensor applications

Persistent Link:
http://hdl.handle.net/10150/282774
Title:
Synthesis and characterization of new octasubstituted phthalocyanines: Supramolecular materials for thin film electronic, optical and chemical sensor applications
Author:
Smolenyak, Paul Eric, 1959-
Issue Date:
1998
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:
The synthesis, structure, and properties of a number of new octasubstituted phthalocyanines, were investigated in this work. Substituent functionality and design has a profound influence on the film forming, and hence, chemical/physical properties of these model molecular electronic materials. Highly ordered thin films, of the benzyl terminated Pc, (2,3,9,10,16,17,23,24-octa(2-benzyloxyethoxy) phthalocyaninato) copper, CuPc(OC₂OBz)₈ and its di-hydrogen analogue were prepared and characterized. These materials form ordered Langmuir films composed of close packed columnar assemblies. Full compression of these materials produces thin films of stable bilayers that show remarkable mechanical stability, and can be transferred with high efficiency to substrates using a horizontal transfer protocol. The physical, spectroscopic, spectroelectrochemical, electrochemical, and electronic properties of these materials were characterized. These properties are strongly dependent on film morphology and structure. The conductivity of these materials relative to the Pc column axis, is highly anisotropic, and with electrochemical doping, the conductivity along the column axis is ca. 10⁻⁶ S/cm. 2,3,9,10,16,17,23,24-Octa(2-benzyloxytriethoxy) phthalocyaninato) copper, and di-hydrogen materials were prepared and characterized. These Pc derivatives did not exhibit the extraordinary properties of their shorter chained analogues. Film preparation efforts with these materials produced poorly ordered isotropic films. Chain length and benzyl termination are combined, in CuPc(OC₂OBz)₈, to produce a unique self assembling material with properties comparable to that reported previously for rigid-rod polymeric Pc materials.
Type:
text; Dissertation-Reproduction (electronic)
Keywords:
Chemistry, Analytical.; Engineering, Materials Science.
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 new octasubstituted phthalocyanines: Supramolecular materials for thin film electronic, optical and chemical sensor applicationsen_US
dc.creatorSmolenyak, Paul Eric, 1959-en_US
dc.contributor.authorSmolenyak, Paul Eric, 1959-en_US
dc.date.issued1998en_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.abstractThe synthesis, structure, and properties of a number of new octasubstituted phthalocyanines, were investigated in this work. Substituent functionality and design has a profound influence on the film forming, and hence, chemical/physical properties of these model molecular electronic materials. Highly ordered thin films, of the benzyl terminated Pc, (2,3,9,10,16,17,23,24-octa(2-benzyloxyethoxy) phthalocyaninato) copper, CuPc(OC₂OBz)₈ and its di-hydrogen analogue were prepared and characterized. These materials form ordered Langmuir films composed of close packed columnar assemblies. Full compression of these materials produces thin films of stable bilayers that show remarkable mechanical stability, and can be transferred with high efficiency to substrates using a horizontal transfer protocol. The physical, spectroscopic, spectroelectrochemical, electrochemical, and electronic properties of these materials were characterized. These properties are strongly dependent on film morphology and structure. The conductivity of these materials relative to the Pc column axis, is highly anisotropic, and with electrochemical doping, the conductivity along the column axis is ca. 10⁻⁶ S/cm. 2,3,9,10,16,17,23,24-Octa(2-benzyloxytriethoxy) phthalocyaninato) copper, and di-hydrogen materials were prepared and characterized. These Pc derivatives did not exhibit the extraordinary properties of their shorter chained analogues. Film preparation efforts with these materials produced poorly ordered isotropic films. Chain length and benzyl termination are combined, in CuPc(OC₂OBz)₈, to produce a unique self assembling material with properties comparable to that reported previously for rigid-rod polymeric Pc materials.en_US
dc.typetexten_US
dc.typeDissertation-Reproduction (electronic)en_US
dc.subjectChemistry, Analytical.en_US
dc.subjectEngineering, Materials Science.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.proquest9912073en_US
dc.identifier.bibrecord.b39115719en_US
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