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由双糠醛组成的生物基聚席夫碱

Biobased Poly(Schiff-Base) Composed of Bifurfural.

作者信息

Tachibana Yuya, Hayashi Senri, Kasuya Ken-Ichi

机构信息

Division of Molecular Science, Faculty of Science and Technology, Gunma University, 1-5-1 Tenjin, Kiryu, Gunma 376-8515, Japan.

Gunma University Center for Food Science and Wellness, 4-2 Aramaki, Maebashi, Gunma 371-8510, Japan.

出版信息

ACS Omega. 2018 May 18;3(5):5336-5345. doi: 10.1021/acsomega.8b00466. eCollection 2018 May 31.

DOI:10.1021/acsomega.8b00466
PMID:31458743
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6641737/
Abstract

In this study, bifurfural, an inedible biobased chemical and a second-generation biomass, was polymerized with several diamines using an environmentally benign process, and the chemical structures of the resulting poly(Schiff base)s were analyzed. Because furan rings, which are only produced from biomass and not from fossil resources, endow polymers with unique properties that include high rigidity and expanded π-conjugation, bifurfural, which contains two furan rings, is of significant interest as a biobased building block. H NMR, IR, and matrix assisted laser desorption ionization-time of flight mass spectra of the poly(Schiff base)s reveal that they are composed of mixtures of linear and cyclic structures. The UV-vis spectroscopy and molecular orbital theory confirm the extended π-conjugation in the bifurfural/-phenylenediamine poly(Schiff base) system. Poly(Schiff base)s composed of bifurfural and 1,3-propanediamine, 1,4-butandiamine, 1,5-pentanediamine, and 1,6-hexanediamine were molded at 120 °C into films that exhibited good strengths and were tough to bend. These results indicate that bifurfural-based poly(Schiff base)s are promising biobased materials.

摘要

在本研究中，二糠醛（一种不可食用的生物基化学品和第二代生物质）通过环境友好型工艺与几种二胺进行聚合反应，并对所得聚席夫碱的化学结构进行了分析。由于呋喃环仅由生物质产生而非化石资源，赋予聚合物独特的性能，包括高刚性和扩展的π共轭，含有两个呋喃环的二糠醛作为生物基构建单元具有重大意义。聚席夫碱的¹H NMR、IR和基质辅助激光解吸电离飞行时间质谱表明它们由线性和环状结构的混合物组成。紫外可见光谱和分子轨道理论证实了二糠醛/对苯二胺聚席夫碱体系中扩展的π共轭。由二糠醛与1,3 - 丙二胺、1,4 - 丁二胺、1,5 - 戊二胺和1,6 - 己二胺组成的聚席夫碱在120°C下模塑成具有良好强度且难以弯曲的薄膜。这些结果表明基于二糠醛的聚席夫碱是有前途的生物基材料。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a662/6641737/9b8a733c6fe8/ao-2018-00466s_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a662/6641737/87847ca7e941/ao-2018-00466s_0011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a662/6641737/df41cc6ba805/ao-2018-00466s_0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a662/6641737/f5aa666a1bce/ao-2018-00466s_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a662/6641737/d5c5898ee115/ao-2018-00466s_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a662/6641737/0638a41b7f50/ao-2018-00466s_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a662/6641737/2cb2555f59ae/ao-2018-00466s_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a662/6641737/422b961e8bf7/ao-2018-00466s_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a662/6641737/40252bb06932/ao-2018-00466s_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a662/6641737/91dcb7df6441/ao-2018-00466s_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a662/6641737/9b8a733c6fe8/ao-2018-00466s_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a662/6641737/87847ca7e941/ao-2018-00466s_0011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a662/6641737/df41cc6ba805/ao-2018-00466s_0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a662/6641737/f5aa666a1bce/ao-2018-00466s_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a662/6641737/d5c5898ee115/ao-2018-00466s_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a662/6641737/0638a41b7f50/ao-2018-00466s_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a662/6641737/2cb2555f59ae/ao-2018-00466s_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a662/6641737/422b961e8bf7/ao-2018-00466s_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a662/6641737/40252bb06932/ao-2018-00466s_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a662/6641737/91dcb7df6441/ao-2018-00466s_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a662/6641737/9b8a733c6fe8/ao-2018-00466s_0008.jpg

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