Memorial University DAI: Synthesis of low band gap polymers

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Title	Synthesis of low band gap polymers
Author	Cammisa, Eduardo G., 1956-
Description	Thesis (M.Sc.)--Memorial University of Newfoundland, 2000. Chemistry
Date	2000
Pagination	xv, 123 leaves : ill.
Subject	Conducting polymers; Energy-band theory of solids
Degree	M.Sc.
Degree Grantor	Memorial University of Newfoundland. Dept. of Chemistry
Discipline	Chemistry
Language	eng
Notes	Bibliography: leaves 95-101
Abstract	A novel synthetic pathway to 4H-cyclopenta[2, l-b:3', 4'-b'] dithiophen-4-one 2-8, which is a valuable precursor for a variety of low band gap polymers, has been developed. From 2-8, the derivatives 4, 4'-bi-(4H cyclopenta[2, l-b:3', 4'-b'] dithiophenylidene) 2-34 and 2, 6-dibromo-4jH cyclopenta[2, l-b:3', 4'-b'] dithiophen-4-one 2-36, were prepared. A poly(4H-cyclopenta[2, l- b:3', 4'-b']dithiophen-4-one) (poly 2-8) film was modified by chemical reaction with Lawesson's reagent giving a new material, which exhibited a smaller band gap (0.8-1.0 eV) than the starting poly 2-8 (1.1-1.2 eV). Compound 2-34 was electrochemically polymerized and cyclic voltammetry showed that the resulting polymer has a low band gap (0.5-0.9 eV), consistent with a theoretical prediction. Compound 2-36 is a useful starting material for the synthesis of new polymers. -- The known compound 2, 2'-(ethyne-l, 2-diyl)bis(thiophene) 3-3 was synthesized using an adaption of a literature procedure, and 3-3 was used for the synthesis of its novel derivatives 4, 5- di-thiophen-2-yl-l, 3-dithiol-2-one 3-5 and tetrathien-2-yl-thiophene 3-6. Electrochemical polymerization of 3-6 gave a polymer with a band gap of ca. 1.8 eV. Dithieno[3, 2-c:2', 3'-e][1, 2] dithiin 4-1 was prepared by using a literature method. Electrochemically prepared films of poly 4-1 did not show any electroactivity for the disulfide bridge in acetonitrile.
Type	Text
Resource Type	Electronic thesis or dissertation
Format	Image/jpeg; Application/pdf
Source	Paper copy kept in the Centre for Newfoundland Studies, Memorial University Libraries
Local Identifier	a1492385
Rights	The author retains copyright ownership and moral rights in this thesis. Neither the thesis nor substantial extracts from it may be printed or otherwise reproduced without the author's permission.
Collection	Electronic Theses and Dissertations
Scanning Status	Completed
PDF File	(24.60 MB) -- http://collections.mun.ca/PDFs/theses/Cammisa_EduardoG.pdf
CONTENTdm file name	26572.cpd