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Download Hi-Res ImageDownload to MS-PowerPointCite This:Macromolecules 2016, 49, 9, 3336-3342
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Ultrastrong, Transparent Polytruxillamides Derived from Microbial Photodimers

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† School of Materials Science, Japan Advanced Institute of Science and Technology, 1-1 Asahidai, Nomi, Ishikawa 923-1292 Japan
‡ Faculty of Life and Environmental Sciences, University of Tsukuba, 1-1-1 Ten-nodai, Tsukuba, Ibaraki 305-8572, Japan
§ Bioorganic Chemistry and Biomaterials Research Group, Department of Chemistry, Faculty of Science, Chulalongkorn University, 254 Pathumwan, Bangkok 10330, Thailand
∥ Key Laboratory of Industrial Biotechnology, Ministry of Education, School of Biotechnology, Jiangnan University, Wuxi 214122, China
*(T.K.) E-mail [email protected]; Tel +81-761-51-1631.
*(N.T.) E-mail [email protected]; Tel +81-029-853-4937.
Cite this: Macromolecules 2016, 49, 9, 3336–3342
Publication Date (Web):April 22, 2016
https://doi.org/10.1021/acs.macromol.6b00220
Copyright © 2016 American Chemical Society
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Abstract

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Ultrastrong and transparent bioplastics are generated from fermented microbial monomers. An exotic aromatic amino acid, 4-aminocinnamic acid, was prepared from a biomass using recombinant bacteria, and quantitatively photodimerized, and diacid and diamino monomers that were both characterized by a rigid α-truxillate structure were generated. These two monomers were polycondensed to create the polyamides with a phenylenecyclobutane repeating backbone such as poly{(4,4′-diyl-α-truxillic acid dimethyl ester) 4,4′-diacetamido-α-truxillamide} which was processed into amorphous fibers and plastic films having high transparency. In spite of noncrystalline structure, mechanical strength of the fiber is 407 MPa at maximum higher than those of other transparent plastics and borosilicate glasses, presumably due to the tentative molecular spring function of the phenylenecyclobutanyl backbone.

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The Supporting Information is available free of charge on the ACS Publications Web site. The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.macromol.6b00220.

  • Experimental section; Figures S1–S9 and Tables S1–S6 (PDF)

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