Laccase-catalyzed oxidative polymerization of aniline dimer (N-phenyl-1,4-phenylenediamine) in aqueous micellar solution of sodium dodecylbenzenesulfonate |
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| Institution: | 1. Institution of the Russian Academy of Sciences, A.N. Bach Institute of Biochemistry of RAS, Leninsky pr., 33, Moscow 119071, Russia;2. Moscow State University of Environmental Engineering, Staraya Basmannaya Str., 21/4, Moscow 105066, Russia;3. N.M. Emanuel Institute of Biochemical Physics, Russian Academy of Sciences, Kosygin Str. 4, 119334 Moscow, Russia;1. Institut für Botanik, Technische Universität Dresden, 01062 Dresden, Germany;2. Mikrobiologie und Biotechnologie, Interfakultäres Institut für Mikrobiologie und Infektionsmedizin, Eberhard Karls Universität Tübingen, Auf der Morgenstelle 28, 72076 Tübingen, Germany;3. Centrum für Biotechnologie, CeBiTec, Universität Bielefeld, Universitätsstr. 27, 33615 Bielefeld, Germany;4. Allgemeine Biochemie, Technische Universität Dresden, 01062 Dresden, Germany;5. The Novo Nordisk Foundation Center for Biosustainability, Technical University of Denmark, Kemitorvet Bygning 220, 2800 Kgs. Lyngby, Denmark;6. German Centre for Infection Research (DZIF), Partner site Tübingen, IMIT, Auf der Morgenstelle 28, 72076 Tübingen, Germany;1. Facultad de Química, Departamento de Alimentos y Biotecnología, Universidad Nacional Autónoma de México, Ciudad Universitaria, Ciudad de México, 04510, Mexico;2. Facultad de Química, Departamento de Ingeniería Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, Ciudad de México, 04510, Mexico;3. Instituto de Física, Universidad Nacional Autónoma de México, Ciudad Universitaria, Ciudad de México, 04510, Mexico;4. Facultad de Química, UNIPREC, Universidad Nacional Autónoma de México, Ciudad Universitaria, Ciudad de México, 04510, Mexico;5. Departamento de Física, Universidad Autónoma Metropolitana − Unidad Iztapalapa, Av. San Rafael Atlixco No. 186, Col. Vicentina, 09340 Ciudad de México, Mexico;6. Unidad de Energía Renovable, Centro de Investigación Científica de Yucatán, Parque Científico Tecnológico de Yucatán, Carretera Sierra Papacal-Chuburná, Km 5, 97302, Sierra Papacal, Yucatán, Mexico;1. Ruđer Bošković Institute, Division of Physical Chemistry, Zagreb, Croatia;2. ETH Zürich, Department of Materials, Vladimir-Prelog-Weg 5, CH-8093 Zürich, Switzerland;3. Max Planck Institute for Chemical Energy Conversion, Mülheim an der Ruhr, Germany |
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| Abstract: | We have studied oxidative polymerization of aniline dimer (N-phenyl-1,4-phenylenediamine) catalyzed by high-redox potential laccase isolated from the fungi Trametes hirsuta (Wulfen) Pilát CF-28. Enzymatic aniline dimer polymerization was performed in aqueous micellar solution of sodium dodecylbenzenesulfonate, the atmospheric oxygen serving as an oxidizer. The resultant dispersion was stable for at least 6 months. The products synthesized were characterized using Fourier transform infrared and UV–vis spectroscopies. MALDI TOF analysis has shown that aniline dimers polymerize to mainly form aniline oligomers with the m/z ratio up to 2180, which corresponds to a polymerization degree of 24 (in terms of aniline subunits). Enzymatically formed aniline oligomers consist for the most part of para-directed units in the form of emeraldine salt. The end product structure depends on the reaction medium pH. Transmission electron microscopy has revealed granular nanoparticles of the reaction product. |
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