Efficient One-Step Synthesis of Catechol Containing Polymers via Friedel–Crafts Alkylation and Their Use for Water Decontamination

IF 5.1 1区化学 Q1 POLYMER SCIENCE

Macromolecules Pub Date : 2024-11-15 DOI:10.1021/acs.macromol.4c02233

Timo Sehn, Nicolai Kolb, Alexander Azzawi, Michael A. R. Meier

引用次数: 0

Abstract

We herein present an efficient one-step synthesis route toward catechol containing polymers from liquid polybutadiene via a simple post polymerization modification (PPM) approach applying acid catalyzed Friedel–Crafts alkylation (FCA). Accordingly, 100% modification of polybutadiene was achieved within 30 min in bulk at 120 °C. The final structure of the polymer was analyzed by ¹H, ¹³C, 2D nuclear magnetic resonance (NMR), infrared (IR), diffusion ordered spectroscopy (DOSY), and size exclusion chromatography (SEC). Material properties were investigated via thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). Subsequent metal ion removal tests revealed excellent extraction efficiencies (86% ≤ Mⁿ⁺_removal < 100%) when using the catechol containing polymer as heavy metal sorbent and thus emphasize a potential application for water purification processes.

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通过 Friedel-Crafts 烷基化一步法高效合成含邻苯二酚聚合物及其在水净化中的应用

我们在此介绍一种高效的一步法合成路线，通过简单的聚合后改性（PPM）方法，应用酸催化的弗里德尔-卡夫斯烷基化（FCA），从液态聚丁二烯合成含邻苯二酚的聚合物。因此，在 120 °C 的条件下，30 分钟内就能对聚丁二烯进行 100% 的批量改性。聚合物的最终结构通过 1H、13C、2D 核磁共振（NMR）、红外（IR）、扩散有序光谱（DOSY）和尺寸排阻色谱（SEC）进行了分析。材料特性通过热重分析（TGA）和差示扫描量热法（DSC）进行了研究。随后的金属离子去除测试表明，使用含邻苯二酚的聚合物作为重金属吸附剂时，萃取效率极高（86% ≤ Mn+ 去除率 <100%），因此强调了其在水净化过程中的潜在应用。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Macromolecules 工程技术-高分子科学

CiteScore

9.30

自引率

16.40%

发文量

942

审稿时长

2 months

期刊介绍： Macromolecules publishes original, fundamental, and impactful research on all aspects of polymer science. Topics of interest include synthesis (e.g., controlled polymerizations, polymerization catalysis, post polymerization modification, new monomer structures and polymer architectures, and polymerization mechanisms/kinetics analysis); phase behavior, thermodynamics, dynamic, and ordering/disordering phenomena (e.g., self-assembly, gelation, crystallization, solution/melt/solid-state characteristics); structure and properties (e.g., mechanical and rheological properties, surface/interfacial characteristics, electronic and transport properties); new state of the art characterization (e.g., spectroscopy, scattering, microscopy, rheology), simulation (e.g., Monte Carlo, molecular dynamics, multi-scale/coarse-grained modeling), and theoretical methods. Renewable/sustainable polymers, polymer networks, responsive polymers, electro-, magneto- and opto-active macromolecules, inorganic polymers, charge-transporting polymers (ion-containing, semiconducting, and conducting), nanostructured polymers, and polymer composites are also of interest. Typical papers published in Macromolecules showcase important and innovative concepts, experimental methods/observations, and theoretical/computational approaches that demonstrate a fundamental advance in the understanding of polymers.