Reactive groups on polymer coated electrodes, 12. New conducting carrier materials: polyalkylthiophene functionalized with amino group and its protected forms

Li, Guangtao; Koßmehl, Gerhard; Kautek, Wolfgang; Plieth, W.; Zhu, Hongbo; Chan, Hardy Sze On; Ng, Siu‐Choon

doi:10.1002/(sici)1521-3935(20000101)201:1<21::aid-macp21>3.0.co;2-r

Cited by 8 publications

(8 citation statements)

References 17 publications

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“…It was considered that monosubstituted pendant thiophene will have more degree of freedom than a backbone containing a 3,4-substituted thiophene ring and will consequently have a greater probability of producing polythiophene chains after oxidative polymerization. In order to increase the probability of producing extensive polythiophene upon thiophene oxidation, the polyimides need to contain a minimum of two CH 2 spacer groups between the thiophene ring and maleimide one [17,18]. However, the successful polymerization of 3-benzylthiophene [19], 3-(N-phtalimidomethyl) thiophene [20] and other aromatic ester or amide-substituted thiophene monomers [21] indicate that it is possible to polymerize thiophene rings which are sterically hindered and contain fewer aliphatic spacer groups.…”

Section: Design and Synthesis Of Monomer Mbthimentioning

confidence: 99%

Synthesis and characterization of alternating copolymers of thiophene-containing N-phenyl maleimide and styrene by photoinduced radical polymerization and their use in electropolymerization

Yılmaz

Cianga

Guner

et al. 2004

Polymer

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Section: Design and Synthesis Of Monomer Mbthimentioning

confidence: 99%

Synthesis and characterization of alternating copolymers of thiophene-containing N-phenyl maleimide and styrene by photoinduced radical polymerization and their use in electropolymerization

Yılmaz

Cianga

Guner

et al. 2004

Polymer

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“…Using this strategy (Figure 1), we report herein the fabrication of submicrometer long conjugated polythiophene molecular wires of molecular thinness in gram‐scale. The surfactants, which function both as template and monomer, trimethyl‐(11‐thiophen‐3‐yl‐undecyl) ammonium bromide ( 2 ) and the pentyl homologue 1 were synthesized by standard methods 14. Mesostructured silicates were synthesized following a slightly modified procedure reported by Ozin et al for the preparation of mesoporous silica with functional organic groups within the channels 15.…”

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confidence: 99%

Gram‐Scale Synthesis of Submicrometer‐Long Polythiophene Wires in Mesoporous Silica Matrices

Bhosale

Wang

et al. 2003

Angew Chem Int Ed

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The mesoporous silica MCM-41 is characterized by ordered hexagonal arrays of uniform channels. The pore diameter can be controlled in the range of 2-10 nm by the synthetic procedures and the surface area is about 1000 m 2 g À1 . [1][2] These attributes make the material attractive not only as sorbent, catalytic support, and separation membrane, but also as ideal host for rational nanomanufacturing, [3][4][5][6][7] especially as synthetic scaffolds for controlled polymerization. [8][9][10][11][12][13] Polyanilin and polyacryl fibers were first synthesized inside MCM-41 by oxidation and free-radical initiation of the corresponding monomers. [8][9] Contactless microwave conductivity measurements displayed a high conductivity of the encapsulated polymer as compared with the bulk polymer. Since then the polymerization of various monomers, such as styrene, alkyne, ethylene, and methylmethacrylate, have been reported within MCM-41. [3][4][5][6][7][8][9][10][11][12][13] The described polymerization processes occur in two steps, 1) loading of the monomer into preformed silica channels by chemical vapor deposition (CVD) or freeze-thaw cycles, and 2) polymerization by irradiation or oxidation.It is conceivable that the structure-directing agents for the silicate, for example, cetyltrimethylammonium bromide, could also bear polymerizable units. Aida and Tajima applied this approach on polyacetylene, but obtained only a few macroscopic rods, with diameters between 15 and 25 mm. [13] We assumed that flexible thiophene units with pentyl or undecyl ammonium side chains may form more fluid, densely packed template monomers and could be directly polymerized in situ in a controllable fashion to linear macromolecular fibers. Using this strategy (Figure 1), we report herein the fabrication of submicrometer long conjugated polythiophene molecular wires of molecular thinness in gram-scale. The surfactants, which function both as template and monomer, trimethyl-(11-thiophen-3-yl-undecyl) ammonium bromide (2) and the pentyl homologue 1 were synthesized by standard methods.[14] Mesostructured silicates were synthesized following a slightly modified procedure reported by Ozin et al. for the preparation of mesoporous silica with functional organic groups within the channels.[15] In a typical synthesis, 1.0 g of tetraethylorthosilicate (TEOS) was added to an aqueous solution of NH 4 OH containing monomer 2 under stirring. The molar ratio of 1.0 Si:114 H 2 O:8.0 NH 4 OH (28 %):0.12 thiophene 2 was thus established in the reaction mixture. After 60 min stirring at room temperature, the solution was left standing at 90 8C for 5 h in a closed polyethylene bottle. A white powder was collected by filtration, washed thoroughly with millipore water, and dried in air. The yield was about 1 g. We assume that all of the thiophene 2 was entrapped in the material, because the filtrate seemed not to contain a detergent. The homologous monomer 1 was less useful as a template, presumably, because of its shorter chain length, it does not form micelles. Figur...

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“…Conductive polymers terminated with primary amine groups could not be obtained directly by electropolymerization of amine functionalized monomers because of the low oxidation potential of amines 9. To obtain the amine functionalized conjugate polymers, tedious protect and deprotect procedures were required 8, 9. Postfunctionalization of conducting polymers using “click” chemistry opens up a new opportunity to circumvent this problem.…”

Section: Resultsmentioning

confidence: 99%

“…Although this strategy is useful and many functional groups were attached onto conductive surfaces, the successful implementation of this strategy depends to a great extent on the compatibility of the functional units introduced with the electropolymerization reaction. In some extreme cases, the polymerization process is completely blocked when substitutes have bulky molecular size8 or possess a lower oxidation potential than that of the corresponding monomers 9. Moreover, due to harsh polymerization conditions, this approach is critical or problematic for the immobilization of sensitive, valuable biomolecules 6…”

Section: Introductionmentioning

confidence: 99%

“…As a result of our continuous interest in the design and functionalization of conducting polymer coated surfaces,9, 10b we were attracted by the recent development of click chemistry, especially the copper (I) catalyzed Huisgen reaction between azide and terminal alkyne. This 1,3‐dipolar cycloaddition reaction is recognized as the best example of click chemistry and can be performed to give a quantitative yield, in multiple solvents (including water) and in the presence of various functional groups, as well as under mild reaction conditions 13.…”

Section: Introductionmentioning

confidence: 99%

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“Click” on Conducting Polymer Coated Electrodes: A Versatile Platform for the Modification of Electrode Surfaces

Zhang

Chang

et al. 2008

Macro Chemistry & Physics

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Two types of N‐substituted pyrroles with azide and terminal alkyne groups have been synthesized and electropolymerized. “Click” chemistry, specifically Huisgen 1,3‐dipolar cycloaddition, was used as a general method for functionalization of the polypyrrole films. Several model compounds, including redox active (quinone), bioactive (cholic acid) and recognition elements (carbohydrate and thymidine) could easily be attached onto the electrode surfaces without loss of functionality or the electroactivity of the underlying conducting polymers. The results suggest that the polypyrrole films are clickable and provide a novel biocompatible and versatile platform for efficient modifications on electrode surfaces.magnified image

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Reactive groups on polymer coated electrodes, 12. New conducting carrier materials: polyalkylthiophene functionalized with amino group and its protected forms

Cited by 8 publications

References 17 publications

Synthesis and characterization of alternating copolymers of thiophene-containing N-phenyl maleimide and styrene by photoinduced radical polymerization and their use in electropolymerization

Synthesis and characterization of alternating copolymers of thiophene-containing N-phenyl maleimide and styrene by photoinduced radical polymerization and their use in electropolymerization

Gram‐Scale Synthesis of Submicrometer‐Long Polythiophene Wires in Mesoporous Silica Matrices

“Click” on Conducting Polymer Coated Electrodes: A Versatile Platform for the Modification of Electrode Surfaces

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