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Jerry L. Reddinger

Bio: Jerry L. Reddinger is an academic researcher from University of Florida. The author has contributed to research in topics: Electrochromism & Polymer. The author has an hindex of 12, co-authored 15 publications receiving 903 citations.

Papers
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Journal ArticleDOI
TL;DR: In this article, the synthesis and electrochemical polymerization of a series of bisheterocycle-N-substituted carbazoles was reported, which exhibits low peak oxidation potentials (Ep,m) which range from 0.15 to 0.46 V vs Ag/Ag+, indicating facile polymerization.
Abstract: We report the synthesis and electrochemical polymerization of a series of bisheterocycle-N-substituted carbazoles. These monomers exhibit low peak oxidation potentials (Ep,m) which range from 0.15 to 0.46 V vs Ag/Ag+, indicating facile polymerization. Repeated scan electrochemical polymerization for these monomers proceeds rapidly, relative to carbazole, to form stable electroactive films. Cyclic voltammetry of the polymers indicates that the films are well adhered to the electrode surface and that each of the polymers possess two distinct redox waves. At applied potentials greater than 1.15 V, a third irreversible oxidative process is observed, presumedly due to cross-linking. Optoelectrochemical analysis indicates that these polymers have an electronic bandgap (measured as the onset of the π-to-π* transition) between 2.4 and 2.5 eV. Three distinct colors are achievable by varying the redox state of the polymers suggesting potential use for multiply colored electrochromic displays. For the series of bis(...

179 citations

Journal ArticleDOI
TL;DR: In this article, the synthesis, characterization, and electrochromic properties of copolymers derived from 9,9-dialkyl-2,7-dibromofluorene (18a, alkyl=C====== 10======H====== 21======
Abstract: The synthesis, characterization, and electrochromic properties of copolymers derived from 9,9-dialkyl-2,7-dibromofluorene (18a, alkyl=C 10 H 21 ; 24, alkyl=Et) and pyrrole, thiophene, 3,4-ethylenedioxythiophene, and furan are described. Two synthetic routes to 9,9-diethyl-2,7-bis(pyrrol-2-yl)fluorene (30) afford product in 30% and 20% yields, respectively. Monomer 30 undergoes electropolymerizationto yield electroactive polymer films. The lowest monomer oxidation potential (E p,m =0.4 V vs. Ag/Ag + ) is found in tetraethylammonium tosylate (TEATOS)-CH 3 CN, but film formation is slow. Spectroelectrochemical analysis of poly(30) reveals a band gap at 2.4 eV and upon polymer oxidation, two low energy absorptions peaking at 1.2 and 2.2 eV appear. This phenomenon is attributed to formation of bipolaron bands between the valence and conduction bands. Soluble fluorene-heterocycle polymers 34a-d have been synthesized by the Stille coupling reaction of 18a and 2,5-bis(trimethylstannyl)thiophene (21a), 5,5′-bis(trimethylstannyl)-2,2′-bithiophene (21b), 2,5-bis(trimethylstannyl)-3,4-ethylenedioxythiophene (21c), and 2,5-bis(trimethylstannyl)furan (22), respectively, in high yields. The NMR spectra are consistent with the proposed structures of the polymers 34a-d, and no evidence of ring opening of the furyl unit in 34d is seen in the NMR and IR spectra. The molecular weights of 34a-d are in the range of 8000 g mol –1 with polydispersity indices (PDI) of 2. Polymers 34a-c have band gaps measured at 2.4 eV, while polymer 34d has its gap at 2.6 eV. Polymers 34a-c undergo solution doping with SbCl 5 to form new low energy bipolaron bands at the expense of the absorption in the UV-VIS. However, polymer 34d does not oxidatively dope with SbCl 5 .

112 citations

Book ChapterDOI
TL;DR: An extensive review of the synthesis of π-conjugated polymers is presented using a tutorial approach to provide an introduction to the field intended for the undergraduate student and the experienced chemist alike as mentioned in this paper.
Abstract: An extensive review of the synthesis of π-conjugated polymers is presented using a tutorial approach to provide an introduction to the field intended for the undergraduate student and the experienced chemist alike. The many synthetic methodologies that have been used for the synthesis of conjugated polymers are outlined for each class of polymers with a focus on research from the 1990s. The effect of structure on electrical properties is detailed. Specific systems reviewed include the polyacetylenes, polyanilines, polypyrroles, polythiophenes, poly(arylene vinylenes), and polyphenylenes.

98 citations


Cited by
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Journal ArticleDOI
TL;DR: School of Chemistry, Bio21 Institute, University of Melbourne, 30 Flemington Road, Victoria 3010, Australia; School of Materials Science and Engineering, Nanyang Technological University, Nastyang Avenue, Republic of Singapore 639798; Institute of Materials Research and Engineering (IMRE) and the Agency for Science, Technology and Research (A*STAR), 3 Research Link, Singapore 117602.
Abstract: A review was presented to demonstrate a historical description of the synthesis of light-emitting conjugated polymers for applications in electroluminescent devices. Electroluminescence (EL) was first reported in poly(para-phenylene vinylene) (PPV) in 1990 and researchers continued to make significant efforts to develop conjugated materials as the active units in light-emitting devices (LED) to be used in display applications. Conjugated oligomers were used as luminescent materials and as models for conjugated polymers in the review. Oligomers were used to demonstrate a structure and property relationship to determine a key polymer property or to demonstrate a technique that was to be applied to polymers. The review focused on demonstrating the way polymer structures were made and the way their properties were controlled by intelligent and rational and synthetic design.

2,378 citations

Journal ArticleDOI
Stephan Kirchmeyer1, Knud Reuter1
TL;DR: In this article, the industrial applications of poly(3,4-ethylenedioxythiophene) and poly(styrene sulfonic acid) poly(poly(3.4)-ethylenedioitriou glycol (PEDT) are summarized.
Abstract: This article summarises the industrial applications of poly-(3,4-ethylenedioxythiophene) (PEDT, PEDOT). The basic chemical and physical properties of PEDT are discussed to outline the fundamentals which lead to PEDT as a highly valuable electric and electronic material. PEDT applications are reviewed depending on the two different ways of preparation: in situ polymerisation of the monomer, usually carried out by the user, and applying the prefabricated polymer in the form of its water-based complex with poly(styrene sulfonic acid). Several applications like antistatic coatings, cathodes in capacitors, through-hole plating, OLED's, OFET's, photovoltaics, and electrochromic applications are discussed in detail.

1,343 citations

Journal ArticleDOI
TL;DR: Dithieno[3,2-b:2′3′-d]thiophene-4,4-dioxides 1221 3.3.1.
Abstract: 3.2. Thienothiophenes 1216 3.2.1. Thieno[3,4-b]thiophene Analogues 1216 3.2.2. Thieno[3,2-b]thiophene Analogues 1217 3.2.3. Thieno[2,3-b]thiophene Analogues 1218 3.3. , ′-Bridged Bithiophenes 1219 3.3.1. Dithienothiophene (DTT) Analogues 1220 3.3.2. Dithieno[3,2-b:2′3′-d]thiophene-4,4-dioxides 1221 3.3.3. Dithienosilole (DTS) Analogues 1221 3.3.4. Cyclopentadithiophene (CPDT) Analogues 1221 3.3.5. Nitrogen and Phosphor Atom Bridged Bithiophenes 1222

1,224 citations

Journal ArticleDOI
TL;DR: Conventional approaches to chemical sensors have traditionally made use of a “lock-and-key” design, wherein a specific receptor is synthesized in order to strongly and highly selectively bind the analyte of interest.
Abstract: Conventional approaches to chemical sensors have traditionally made use of a “lock-and-key” design, wherein a specific receptor is synthesized in order to strongly and highly selectively bind the analyte of interest.1-6 A related approach involves exploiting a general physicochemical effect selectively toward a single analyte, such as the use of the ionic effect in the construction of a pH electrode. In the first approach, selectivity is achieved through recognition of the analyte at the receptor site, and in the second, selectivity is achieved through the transduction process in which the method of detection dictates which species are sensed. Such approaches are appropriate when a specific target compound is to be identified in the presence of controlled backgrounds and interferences. However, this type of approach requires the synthesis of a separate, highly selective sensor for each analyte to be detected. In addition, this type of approach is not particularly useful for analyzing, classifying, or assigning human value judgments to the composition of complex vapor mixtures such as perfumes, beers, foods, mixtures of solvents, etc.

1,192 citations