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Design, Synthesis, and Adhesion of Fluorescent Conjugated Polymers with Pendant Catechol Groups
ACS Applied Polymer Materials ( IF 4.4 ) Pub Date : 2021-08-11 , DOI: 10.1021/acsapm.1c00603 Hao Zhan 1 , Jiajun Chen 1 , Chi Zhang 1 , Jincheng Zhang 1 , Li-Juan Fan 1
ACS Applied Polymer Materials ( IF 4.4 ) Pub Date : 2021-08-11 , DOI: 10.1021/acsapm.1c00603 Hao Zhan 1 , Jiajun Chen 1 , Chi Zhang 1 , Jincheng Zhang 1 , Li-Juan Fan 1
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Incorporating conjugated polymers with functionalities to provide good adhesion to solid substrates is favorable to prepare fluorescent solid materials for various applications. Inspired by the wide range and robust adhesion property of mussel, a series of conjugated polymers with the poly[p-(phenylene ethynylene)-alt-(thienylene ethynylene)] backbone and pendant catechol groups via Sonogashira coupling polymerization were designed and synthesized. The contents of catechol groups were precisely tuned through copolymerization, followed by selective deprotection. For comparison, similar polymers with pendant phenol groups were also synthesized. The conjugated polymers were demonstrated to have expected chemical structures via systematic characterizations. All the polymers had good solubility in common organic solvents and displayed strong fluorescence in solution. To evaluate the adhesion performance of different polymers, fluorescent silica microspheres were selected as the substrate for loading the abovementioned polymers via immersing the silica microspheres into solutions of conjugated polymers. To find out the loading amount, a calibration curve for each polymer was set up based on the linear relationship between the fluorescence intensities of the suspension of microspheres and the polymer concentrations. The loading amounts of catechol-functionalized polymers were significantly higher than those of phenol-functionalized polymers; the highest loading amount is over 14-fold of the amount of the control polymer without any catechol/phenol functionality. By combining the abovementioned results with the preliminary mechanism investigation based on the solvent washing, it was concluded that catechol functionality and its content in the polymers greatly affected the adhesion performance. The multidentate interaction provided by catechol groups may enable the conjugated polymers to be widely used for fluorescence coating and staining of a variety of substrates.
中文翻译：
具有邻苯二酚侧基的荧光共轭聚合物的设计、合成和粘附
掺入具有功能性的共轭聚合物以提供对固体基材的良好粘附性，有利于制备用于各种应用的荧光固体材料。受贻贝广泛和强大的粘附特性的启发，一系列共轭聚合物与聚[ p -（亚苯基乙炔）- alt-(thienylene ethynylene)]骨架和邻苯二酚侧基通过Sonogashira偶联聚合被设计和合成。儿茶酚基团的含量通过共聚精确调节，然后选择性脱保护。为了进行比较，还合成了具有苯酚侧基的类似聚合物。通过系统表征证明共轭聚合物具有预期的化学结构。所有聚合物在普通有机溶剂中均具有良好的溶解性，并在溶液中显示出强烈的荧光。为了评估不同聚合物的粘附性能，选择荧光二氧化硅微球作为基材，通过将二氧化硅微球浸入共轭聚合物溶液中来负载上述聚合物。要找出装载量，根据微球悬浮液的荧光强度与聚合物浓度之间的线性关系，建立了每种聚合物的校准曲线。儿茶酚官能化聚合物的负载量显着高于苯酚官能化聚合物的负载量；最高负载量是不含任何儿茶酚/苯酚官能团的对照聚合物量的 14 倍以上。通过将上述结果与基于溶剂洗涤的初步机理研究相结合，得出结论，儿茶酚官能度及其在聚合物中的含量极大地影响了粘附性能。邻苯二酚基团提供的多齿相互作用可以使共轭聚合物广泛用于各种基材的荧光涂层和染色。
更新日期：2021-09-10
中文翻译：
具有邻苯二酚侧基的荧光共轭聚合物的设计、合成和粘附
掺入具有功能性的共轭聚合物以提供对固体基材的良好粘附性，有利于制备用于各种应用的荧光固体材料。受贻贝广泛和强大的粘附特性的启发，一系列共轭聚合物与聚[ p -（亚苯基乙炔）- alt-(thienylene ethynylene)]骨架和邻苯二酚侧基通过Sonogashira偶联聚合被设计和合成。儿茶酚基团的含量通过共聚精确调节，然后选择性脱保护。为了进行比较，还合成了具有苯酚侧基的类似聚合物。通过系统表征证明共轭聚合物具有预期的化学结构。所有聚合物在普通有机溶剂中均具有良好的溶解性，并在溶液中显示出强烈的荧光。为了评估不同聚合物的粘附性能，选择荧光二氧化硅微球作为基材，通过将二氧化硅微球浸入共轭聚合物溶液中来负载上述聚合物。要找出装载量，根据微球悬浮液的荧光强度与聚合物浓度之间的线性关系，建立了每种聚合物的校准曲线。儿茶酚官能化聚合物的负载量显着高于苯酚官能化聚合物的负载量；最高负载量是不含任何儿茶酚/苯酚官能团的对照聚合物量的 14 倍以上。通过将上述结果与基于溶剂洗涤的初步机理研究相结合，得出结论，儿茶酚官能度及其在聚合物中的含量极大地影响了粘附性能。邻苯二酚基团提供的多齿相互作用可以使共轭聚合物广泛用于各种基材的荧光涂层和染色。
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