Enzymatic Synthesis of Fluorescent Naphthol-Based Polymers

Premachandran, R.S.; Banerjee, Soumitro; Wu, Xiaodong; John, Vijay T.; McPherson, Gary L.; Akkara, Joseph A.; Ayyagari, Madhu S.; Kaplan, David L.

doi:10.1021/ma960468f

Cited by 123 publications

(75 citation statements)

References 26 publications

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“…The polymer showed activity at the air-water interface unlike the corresponding monomer, with aggregates under identical conditions. Premachandran et al [63] reported the enzymatic synthesis of fluorescent naphtholbased polymers. In recent years, fluorescent polymers have attracted considerable attention because of their applications in plastic scintillators [64], luminescent solar concentrators [65], high laser-resistant materials [66], laser dyes [67], and fiber optic sensors [68].…”

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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Section: Kobayashi Etmentioning

confidence: 99%

Enzyme-catalyzed polymerization: an opportunity for innovation

Nayak

1998

Designed Monomers and Polymers

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“…Efforts were focused to improve the electrooptical properties of polyphenols with longer conjugated segments. Premachandran et al [7] reported the synthesis of naphthol-based polymers to increase the conjugation lengths in the backbone. The polyphenols with longer conjugation lengths in polymer main chain and pendent groups have also been reported by Kayak et al [8].…”

Section: Introductionmentioning

confidence: 99%

Poly(phenoxy-imine)s and Poly(phenoxy-ketimine)s: Toward New Semiconductive Polymeric Materials

Demir¹

2017

MOJPS

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Conjugated polymers have attracted widespread interest during the last three decades, because of their useful electronic properties. In this paper we discuss semi-conductive properties of the conjugated polymers with phenylhydrazono (C 6 H 5 -NH-N=C-(R/H)-) pendent groups, such as poly(phenoxy-imine)s and poly(phenoxy-ketimine)s. These polymers were found to possess the conductivity of 10 -3 -10 -2 S/cm. It is supposed that high conductivities of the polymers are due to their phenylhydrazono type structures with π-conjugation with participation of the nitrogen atoms in polymer side groups.Keywords: Conjugated polymers; Semi-conductive polymer; Poly(phenoxy-imine) s; Poly(phenoxy-ketimine)s; Oxidative coupling polymerization; Gel permeation chromatography Poly(phenoxy-imine)s and Poly(phenoxy-ketimine)s: Toward New Semiconductive Polymeric Materials 2/6Copyright: ©2017 Demir literature (As can be seen in Supplementary Information, (Table 1-3). They can be seen that the highest conductivity values belong to poly(4-PHMP) and poly(3-PHEP). This is because of the polyconjugated structures of the polymers with phenylhydrazono pendent groups that increase electrical conductivity values. Having this feature, these polyphenols step forwards in comparison with other imine-substituted polyphenols. The results obtained in this study are compatible with the values in literature. *: These data demostrated the maximum (or saturated) conductivity after iodine doping. 2/6 Poly(phenoxy-imine)s and Poly(phenoxy-ketimine)s: Toward New Semiconductive Polymeric Materials 5/6Copyright: ©2017 Demir Further work is being carried out in our laboratory to synthesis and characterization of other polyphenols containing phenylhydrazono pendent groups and to investigation of their properties such as conductivity and some properties. These results will be published soon in a full paper. AcknowledgementThe author thanks Dr. Ilkay Ozaytekin for measuring the electrical conductivity. Conflict of InterestNone.

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“…The reaction of phenols and anilines with hydrogen peroxide catalyzed by different oxidoreductases is an alternative ecofriendly route to synthesize the industrially important polyaromatics. [9][10][11][12][13][14][15][16] Similarly the vinylic monomers have also been polymerized with hydrogen peroxide catalyzed by HRP and related enzymes under milder conditions with high yields. The formation of polymer 2 was indicated in the absence of a peak at 1612 cm -1 for olefinic stretching and a carbonyl absorption from 1672 to 1655 cm -1 in its IR spectra.…”

Section: Introductionmentioning

confidence: 99%

Biomimetic polymerization of acrylamide with hydrogen peroxide catalyzed by water-soluble anionic iron(III) 5,10,15,20-tetrakis-(2',6'-dichloro-3'-sulfonatophenyl)porphyrin

Angrish¹,

Chauhan²

2004

Arkivoc

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The biomimetic polymerization of acrylamide (1) with hydrogen peroxide catalyzed by water soluble iron(III) 5,10,15,20-tetrakis-(2′,6′-dichloro-3′-sulfonatophenyl)porphyrin (3) gave high yield of polyacrylamide (2) in the molecular weight range of 1,30,000-1,50,000 g mol -1 in the absence and presence of 2,4-pentanedione at an ambient temperature in nitrogen atmosphere. The molar ratio of 3: H 2 O 2 : 1 was 1: 100: 3300. Yields were high at pH 4.5 but dropped at pH 7.2. Finally no polymer was formed at pH 9.2 in the absence of 2,4-pentanedione, whereas the yield raised to 99% in the presence of 2,4-pentanedione.

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Enzymatic Synthesis of Fluorescent Naphthol-Based Polymers

Cited by 123 publications

References 26 publications

Enzyme-catalyzed polymerization: an opportunity for innovation

Enzyme-catalyzed polymerization: an opportunity for innovation

Poly(phenoxy-imine)s and Poly(phenoxy-ketimine)s: Toward New Semiconductive Polymeric Materials

Biomimetic polymerization of acrylamide with hydrogen peroxide catalyzed by water-soluble anionic iron(III) 5,10,15,20-tetrakis-(2',6'-dichloro-3'-sulfonatophenyl)porphyrin

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