New Type of π-Conjugated Polymers Constituted of Quinone Units in the Main Chain

Etori, Hideki; Kanbara, Takaki; Yamamoto, Takakazu

doi:10.1246/cl.1994.461

Cited by 28 publications

(17 citation statements)

References 8 publications

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“…Figure 14 depicts CV charts of P(2-Me-1,4-AQ) and its corresponding low molecular weight quinone; the CV of P(2-Me-1,4-AQ) is discussed based on a mixed oxidized state (Scheme 8). 146,174 Comparison of the CV charts (a) and (c) reveals that the CV peaks of P(2-Me-1,4-AQ) are broadened and the potentional difference (∆E) between the two reduction peaks is smaller with P(2-Me-1,4-AQ) (∆E = 0.3 V) than with its corresponding low molecular weight quinone (∆E = 0.6 V). If the electron exchange between the three redox active species (Scheme 8) occurs at infinitely high rate, the two peaks are considered to coalesce.…”

Section: Figurementioning

confidence: 99%

Synthesis of π-Conjugated Polymers Bearing Electronic and Optical Functionalities by Organometallic Polycondensations. Chemical Properties and Applications of the π-Conjugated Polymers

Yamamoto¹

2003

Synlett

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107

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Various π-conjugated polymers have been obtained by using organometallic polycondensations mediated by organotransition metal complexes. For example, Ni(0) complex-promoted dehalogenation polycondensation of dihaloaromatic compounds XAr-X affords poly(arylene)s, -(-Ar-)-n . Pd-catalyzed polycondensation gives poly(arylene-ethynylene)s, -(-Ar-C≡C-Ar′-C≡C-)-n . These polymers are electrochemically active, electrically conductive, and light-emitting. Their well-characterized linear structure brings about unique packing of the polymer molecules in the solid. In this review, we report their synthesis by organometallic polycondensations, their basic properties, the ordered structure in the solid, and applications for electronic and optical devices of π-conjugated polymers.

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Section: Figurementioning

confidence: 99%

Synthesis of π-Conjugated Polymers Bearing Electronic and Optical Functionalities by Organometallic Polycondensations. Chemical Properties and Applications of the π-Conjugated Polymers

Yamamoto¹

2003

Synlett

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107

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“…On the other hand, polymer materials constituted of quinone units capable of reversible redox reactions also have been studied in electroanalytical purposes [6][7][8] an enzymatic method has been reported by Wang et al [9,10] and the particular product, poly(hydroquinone), has been revealed to possess higher degree of polymerization with higher solubility into some common solvents. These potential advantages of the enzymatically prepared PHQ seem to make itself a particularly interesting class of redox polymer in chemically modified electrode applications.…”

Section: Introductionmentioning

confidence: 99%

Poly(hydroquinone)-coated electrode for immobilizing of 5′-amine functioned capture probe DNA and electrochemical response to DNA hybridization

Nakano¹,

Hirayama²,

Toguchi³

et al. 2006

Science and Technology of Advanced Materials

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Enzymatically polymerized hydroquinone, PHQ, was applied for polymer-coated electrode whose surface was further modified with 5 0 -amine dodecamer DNAs (capture probe DNA, CP-DNA) by taking advantage of Michael reaction. The film-forming property of PHQ on graphite substrate surfaces was confirmed to be satisfactory by AFM imaging. Cyclic voltammetric (CV) measurements showed that the PHQ-modified graphite electrode gave well-defined redox waves showing characteristics for surface process. The pH dependence of the formal potential, E 1/2 , suggested that the electrode reaction occurred by two-proton and two-electron mechanism (À59 mV per a pH decade). CVs also gave the specific amount of PHQ adsorption of 0.52 or 0.83 nmol cm À2 (monomer unit) for the different electrode preparations. This was indicative of two-or three-monolayer adsorption of PHQ. For applications of gene detection, the immobilization reaction including the CP-DNA hybridization was studied by microgravimetric analysis using a quartz-crystal microbalance (QCM). Summaries for the two different runs were 1.01 and 0.69 nmol cm À2 (monomer unit) for PHQ adsorption on gold surfaces, 0.19 and 0.15 nmol cm À2 for CP-DNA attachment on the PHQ/Au, and 0.14 and 0.11 nmol cm À2 for hybridization with the complementary DNA on the CP-DNA/PHQ/Au, respectively. Importantly, monitoring of the series of the experiments were possible by measuring the voltammetric properties of the electrode; the distinct redox waves due to PHQ-electrode reaction are suppressed upon immobilizing of the CP-DNA, and its hybridization further suppressed the redox activity. Neither treating of the PHQ-electrode with native DNAs nor treating of CP-DNA/PHQ-electrode with non-target DNA gave no noticeable responses. A possible mechanism for the electrode response was discussed briefly based on electrochemical QCM measurements. We think these observations are important as the basis of DNA hybridization sensor that enables totally, label-free electrochemical detection of the target DNA. r

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“…Poly(quinone)s are typically prepared via chemical and electrochemical [70] methodologies and invariably involve complex processes that are difficult to scale and produce a large amount of products. An alternative method is to synthesize them using enzymes.…”

Section: Kobayashi Etmentioning

confidence: 99%

Enzyme-catalyzed polymerization: an opportunity for innovation

Nayak

1998

Designed Monomers and Polymers

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Abstract�The application of enzymes in organic synthesis has attracted the attention of many research workers in recent years. Specific enzymatic catalysis is expected to synthesize polymers with high selectivity and/or novel structures. Up to now, the enzymatic synthesis of polyphenols, cellulose, lignin, and polypeptides, as well as non-natural polymers, has been successfully achieved. This review discusses the systematic synthesis of polyphenols using horseradish peroxidase-hydrogen peroxide (HRP-H2O2), the ring-opening polymerization of lactones using the enzyme lipase, and the successful synthesis of cellulose using the enzyme cellulase. The polyphenols enzymatically synthesized have been explored as substitutes of phenol-formaldehyde resins to eliminate the pollution caused by formaldehyde in the environment. Due to their unique π-conjugation nature, these polymers have potential applications in nonlinear optics and in the fabrication of light-emitting diodes. The enzymatic polymerizations using lipase have been expanded to ring-opening polymerization and copolymerization of medium-sized lactones yielding polyesters. It is predicted that enzymatic polymerization will revolutionize the polymer and plastics industries in the 21st century for the synthesis of novel polymers with specific properties.

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New Type of π-Conjugated Polymers Constituted of Quinone Units in the Main Chain

Cited by 28 publications

References 8 publications

Synthesis of π-Conjugated Polymers Bearing Electronic and Optical Functionalities by Organometallic Polycondensations. Chemical Properties and Applications of the π-Conjugated Polymers

Synthesis of π-Conjugated Polymers Bearing Electronic and Optical Functionalities by Organometallic Polycondensations. Chemical Properties and Applications of the π-Conjugated Polymers

Poly(hydroquinone)-coated electrode for immobilizing of 5′-amine functioned capture probe DNA and electrochemical response to DNA hybridization

Enzyme-catalyzed polymerization: an opportunity for innovation

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