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Synthesis and characterizations of pyridinium salts including poly(pyridinium salt)s and their applications

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Pyridinium salts, both molecular and polymeric, are an interesting class of multifunctional materials that exhibit liquid-crystalline and light-emitting properties. Moreover, their properties can be easily tuned by introducing new types of anions or by modifying their chemical structures. This dissertation describes synthesis and characterization of poly(pyridinium salt)s containing macrocounterions and fluorene moieties in their backbones, synthesis and characterization of nanocomposites of poly(pyridinium salt)s with single-walled carbon nanotubes via non-covalent interactions, and synthesis and characterizations of pyridinium salts having different aliphatic linkages and their application in organic acid sensing. First, all of these ionic polymers were prepared by either ring-transmutation or by metathesis reaction. Their chemical structures were established by FTIR, 1H spectroscopy and elemental analysis. Some polymers containing macrocounterions had relatively low melting transitions above which they formed thermotropic liquid-crystalline phase; and other polymers were amorphous as determined by VTXRD studies. Ionic polymers containing fluorene moieties in their backbones exhibited lyotropic properties in both iv polar protic and aprotic solvents at various critical concentrations. Light emission properties of this class of polymers in common organic solvents as well as in water and in solid states were also studied. To explore the application of poly(pyridinium salt)s, we developed a method of preparation of nano-composites with a number of poly(pyridinium salt)s and single-walled carbon nanotubes. The single-walled carbon nanotubes were effectively dispersed with various poly(pyridinium salt)s resulting in nanocomposites. The optical and solution properties of these composites were examined by a number of experimental techniques. Finally, some of the synthesized dicationic salts exhibited ionic liquid properties, but all exhibited fluorescent properties in solution and solid states. Due to the presence of methyl orange counterions, pyridinium salts could serves as a pH sensor in organic solvents.

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UNLV Theses, Dissertations, Professional Papers, and Capstones


12-1-2012

Synthesis and characterizations of pyridinium salts including
poly(pyridinium salt)s and their applications
Tae Soo Jo
University of Nevada, Las Vegas




Follow this and additional works at: https://digitalscholarship.unlv.edu/thesesdissertations

Part of the Nanoscience and Nanotechnology Commons, and the Polymer Chemistry Commons


Repository Citation
Jo, Tae Soo, "Synthesis and characterizations of pyridinium salts including poly(pyridinium salt)s and their
applications" (2012). UNLV Theses, Dissertations, Professional Papers, and Capstones. 1743.
http://dx.doi.org/10.34917/4332724


This Dissertation is protected by copyright and/or related rights. It has been brought to you by Digital
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,SYNTHESIS AND CHARACTERIZATIONS OF PYRIDINIUM SALTS INCLUDING

POLY(PYRIDINIUM SALT)S AND THEIR APPLICATIONS




By




Tae Soo Jo


Bachelor of Chemical Engineering
Kwangwoon University
2004

Master of Chemical Engineering
Yonsei University
2006




A dissertation submitted in partial fulfillment
of the requirements for the


Doctor of Philosophy in Chemistry


Department of Chemistry
College of Sciences
Graduate College




University of Nevada, Las Vegas
December 2012

,THE GRADUATE COLLEGE


We recommend the dissertation prepared under our supervision by

Tae Soo Jo

entitled

Synthesis and Characterizations of Pyridinium Salts Including Poly(Pyridinium Salt)s
and their Applications


be accepted in partial fulfillment of the requirements for the degree of



Doctor of Philosophy in Chemistry
Department of Chemistry

Pradip Bhowmik, Ph.D., Committee Chair

Kathleen Robins, Ph.D., Committee Member

Vernon Hodge, Ph.D., Committee Member

Laxmi Gewali, Ph.D., Graduate College Representative

Tom Piechota, Ph.D., Interim Vice President for Research &
Dean of the Graduate College

December 2012




ii

, ABSTRACT


Synthesis and Characterizations of Pyridinium Salts Including Poly(pyridinium salt)s and

Their Applications

by

Tae Soo Jo

Dr. Pradip K. Bhowmik, Examination Committee Chair
Department of Chemistry
University of Nevada La Vegas


Pyridinium salts, both molecular and polymeric, are an interesting class of

multifunctional materials that exhibit liquid-crystalline and light-emitting properties.

Moreover, their properties can be easily tuned by introducing new types of anions or by

modifying their chemical structures. This dissertation describes synthesis and

characterization of poly(pyridinium salt)s containing macrocounterions and fluorene

moieties in their backbones, synthesis and characterization of nanocomposites of

poly(pyridinium salt)s with single-walled carbon nanotubes via non-covalent interactions,

and synthesis and characterizations of pyridinium salts having different aliphatic linkages

and their application in organic acid sensing.

First, all of these ionic polymers were prepared by either ring-transmutation or by

metathesis reaction. Their chemical structures were established by FTIR, 1H spectroscopy

and elemental analysis. Some polymers containing macrocounterions had relatively low

melting transitions above which they formed thermotropic liquid-crystalline phase; and

other polymers were amorphous as determined by VTXRD studies. Ionic polymers

containing fluorene moieties in their backbones exhibited lyotropic properties in both
iii
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