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Increasingly functional poly(3,4-alk...

Jones, Adolphus Genay.

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Increasingly functional poly(3,4-alkylenedioxythiophene)s through facile substitution.

Record Type:	Language materials, printed : Monograph/item
Title/Author:	Increasingly functional poly(3,4-alkylenedioxythiophene)s through facile substitution./
Author:	Jones, Adolphus Genay.
Description:	149 p.
Notes:	Adviser: John R. Reynolds.
Contained By:	Dissertation Abstracts International68-12B.
Subject:	Chemistry, Organic. -
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3293953
ISBN:	9780549379942

Increasingly functional poly(3,4-alkylenedioxythiophene)s through facile substitution.
Jones, Adolphus Genay.

Increasingly functional poly(3,4-alkylenedioxythiophene)s through facile substitution. - 149 p.

Adviser: John R. Reynolds.

Thesis (Ph.D.)--University of Florida, 2007.

This work presents the development of a series of poly(3,4-akylenedioxythiophene)s with the potential to be applied in sensors, batteries, capacitors, light emitting devices, and photovoltaic power generation. Both alkoxy and aryloxy 3, 4-propylenedoxythiophene derivatives were prepared via Williamson etherification of the appropriate alcohol and a keystone molecule, 2,2-bis(bromomethyl)-3,4-propylenedioxythiophene. The resulting monomers were purified and fully characterized, then subsequently polymerized via Grignard Metathesis or electrochemical deposition. The optoelectronic properties of the polymers were then studied and compared to similar materials.

ISBN: 9780549379942Subjects--Topical Terms:

516206
Chemistry, Organic.

Increasingly functional poly(3,4-alkylenedioxythiophene)s through facile substitution.
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020 $a 9780549379942
035 $a (UMI)AAI3293953
035 $a AAI3293953
040 $a UMI $c UMI
100 1 $a Jones, Adolphus Genay. $3 1280774
245 1 0 $a Increasingly functional poly(3,4-alkylenedioxythiophene)s through facile substitution.
300 $a 149 p.
500 $a Adviser: John R. Reynolds.
500 $a Source: Dissertation Abstracts International, Volume: 68-12, Section: B, page: 8056.
502 $a Thesis (Ph.D.)--University of Florida, 2007.
520 $a This work presents the development of a series of poly(3,4-akylenedioxythiophene)s with the potential to be applied in sensors, batteries, capacitors, light emitting devices, and photovoltaic power generation. Both alkoxy and aryloxy 3, 4-propylenedoxythiophene derivatives were prepared via Williamson etherification of the appropriate alcohol and a keystone molecule, 2,2-bis(bromomethyl)-3,4-propylenedioxythiophene. The resulting monomers were purified and fully characterized, then subsequently polymerized via Grignard Metathesis or electrochemical deposition. The optoelectronic properties of the polymers were then studied and compared to similar materials.
520 $a The first group of polymers studied was based on derivatization with linear alcohols, Octyl and decyl alcohol were used to produce polymer films via electrochemical deposition and soluble polymers via Grignard Metathesis polymerization. After purification by Soxhlet extraction, the chemically synthesized polymers, PProDOT-(CH2OC8H17)2 and PProDOT-(CH2OC10H21)2, gave Mn values of 38 kDa and 57 kDa by gel permeation chromatography in tetrahydrofuran. When compared, the optoelectronic properties of PProDOT-(CH 2OC8H17)2 showed a maximum absorption at 574 nm, or approximately 2.2 eV, and PProDOT-(CH2OC10H 21)2 had a higher absorption at 584 nm, equivalent to 2.1 eV. The chemically polymerized analogues showed similar maximum absorptions near 597 nm. Both polymers were electrochromic, switching from deep purple to a transmissive, sky blue upon oxidation. The colorimetrically determined luminance change (Delta%Y) for these alkoxy substituted PProDOTs is 60%, while the contrast at lambdamax (Delta%T) between colored and transmissive states is 62%. The coloration efficiency of both polymers was determined with PProDOT-(CH2OC10H21) 2 giving a maximum value of 1020 cm2/C.
520 $a Aryl substituted polymers were synthesized to expand the PProDOT family, and to study the influence of aryl groups on ordering. Commercial phenol and cresol were used to obtain the desired monomers which showed interesting packing structures by x-ray crystallography. Both ProDOT-(CH2OC6H 5)2 and ProDOT-(CH2OPhMe)2 crystals aligned such that the thiophene of one monomer lay between the substituent aryl rings of another monomer. The crystal structure of ProDOT-(CH2OPhMe) 2 suggested a much more open spacing, due to the accommodation of the methyl substituents, while ProDOT-(CH2OC6H5) 2 took a herringbone order with the sulfur atoms between nearby aryl rings. The monomers were then electrochemically polymerized to give films which were characterized as electrochromic materials. Both polymers had band gaps near 2.1 eV, oxidize to transmissive, grey films, and had luminance changes smaller than the alkoxy PProDOTs with values of 36% and 45% being observed for ProDOT-(CH2OC6H5)2 and ProDOT-(CH 2OPhMe)2, respectively. PProDOT-(CH2OC6H 5)2 showed a higher composite coloration efficiency of 581 cm2/C than PProDOT-(CH2OPhMe)2 at 377 cm2/C.
520 $a The final series of polymers was based on electron-poor phenols that could undergo reductive electrochemistry. Synthesized similarly to the previous compounds, pentafluorphenyl, ethyl benzyl, and cyanophenyl derivatives of poly(3,4-propylenedioxythiophene) were obtained after electrochemical polymerization. These molecules also demonstrated aryl-controlled ordering in the solid state, especially for PProDOT-(OC6F5)2, where a F-F interaction was observed. Electrochromic properties consistent with the previous aryl substituted PProDOTs were also observed. The reductive electrochemistry was studied using differential pulse voltammetry with only PProDOT-EB showing a reversible electrochemical cycle at E1/2 = -1.8 V versus ferrocene. This work expands the 3, 4-propylenedioxythiophene structural family of polymers, and provides a foundation for the use of aryl substituents as a means of controlling order in conjugated polymers.
590 $a School code: 0070.
650 4 $a Chemistry, Organic. $3 516206
650 4 $a Chemistry, Polymer. $3 1018428
690 $a 0490
690 $a 0495
710 2 $a University of Florida. $3 718949
773 0 $t Dissertation Abstracts International $g 68-12B.
790 $a 0070
790 1 0 $a Reynolds, John R., $e advisor
791 $a Ph.D.
792 $a 2007
856 4 0 $u http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3293953