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Polymerization of Diamines with Sulfur Monochloride To Yield Bright, Conjugated Polymers
Macromolecules ( IF 5.1 ) Pub Date : 2024-09-10 , DOI: 10.1021/acs.macromol.4c00989 Shanari M. R. Wickremasinghage 1 , Matthew A. Breuer 2 , Ned B. Bowden 1
Macromolecules ( IF 5.1 ) Pub Date : 2024-09-10 , DOI: 10.1021/acs.macromol.4c00989 Shanari M. R. Wickremasinghage 1 , Matthew A. Breuer 2 , Ned B. Bowden 1
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Highly conjugated polymers possessing the NSS functional group were synthesized to investigate the colors obtained from polymers with this understudied functional group. Five aromatic diamines were polymerized with sulfur monochloride (S2Cl2) to yield high molecular weight cross-linked polymers. The polymerizations were completed with ratios of amine to sulfur monochloride of 1.5:1, 1:1, 1:1.5, and 1:2 to yield polymers with different levels of cross-linking and molecular weights from 15 to 5100 kg mol–1. The compositions were investigated by elemental analysis to confirm that the amount of sulfur within the polymers agreed with predictions based on the ratio of monomers used in their synthesis. These polymers were brightly colored with colors from yellow, red, brown, green, and blue, and their UV–vis spectra were measured to determine the absorption maxima. Several control experiments were completed that demonstrated that the reactions between monomers occurred between the amines and S2Cl2 rather than electrophilic aromatic substitution reactions. The polymers were air stable but completely degraded in the presence of 2-mercaptoethanol. In each of these degradations, the diamine monomer was isolated without any evidence of a thiol on the ring, as would be expected for electrophilic aromatic substitution. These polymers were investigated for their ability to act as sensors for 2-mercaptoethanol by exposing them to 2-mercaptoethanol and measuring the change in the color. The reactions between the amines and S2Cl2 were rapid and used to print 2D objects with a variety of colors.
中文翻译：
二胺与一氯化硫聚合生成光亮的共轭聚合物
合成了具有 NSS 官能团的高度共轭聚合物，以研究从具有该待研究官能团的聚合物获得的颜色。五种芳香族二胺与一氯化硫（S 2 Cl 2 ）聚合生成高分子量交联聚合物。胺与一氯化硫的比例为 1.5:1、1:1、1:1.5 和 1:2 时完成聚合，得到具有不同交联水平和分子量从 15 到 5100 kg mol –1 的聚合物。通过元素分析研究了这些组合物，以确认聚合物中的硫含量与基于其合成中所用单体的比例的预测相符。这些聚合物颜色鲜艳，有黄色、红色、棕色、绿色和蓝色，测量它们的紫外-可见光谱以确定吸收最大值。完成了几个对照实验，证明单体之间的反应发生在胺和S 2 Cl 2之间，而不是亲电芳族取代反应。该聚合物在空气中稳定，但在 2-巯基乙醇存在下完全降解。在每一次降解中，二胺单体都被分离出来，环上没有任何硫醇的证据，正如亲电芳族取代所预期的那样。通过将这些聚合物暴露于 2-巯基乙醇并测量颜色变化，研究了它们作为 2-巯基乙醇传感器的能力。胺和 S 2 Cl 2之间的反应很快，可用于打印各种颜色的 2D 物体。
更新日期：2024-09-10
中文翻译：
二胺与一氯化硫聚合生成光亮的共轭聚合物
合成了具有 NSS 官能团的高度共轭聚合物，以研究从具有该待研究官能团的聚合物获得的颜色。五种芳香族二胺与一氯化硫（S 2 Cl 2 ）聚合生成高分子量交联聚合物。胺与一氯化硫的比例为 1.5:1、1:1、1:1.5 和 1:2 时完成聚合，得到具有不同交联水平和分子量从 15 到 5100 kg mol –1 的聚合物。通过元素分析研究了这些组合物，以确认聚合物中的硫含量与基于其合成中所用单体的比例的预测相符。这些聚合物颜色鲜艳，有黄色、红色、棕色、绿色和蓝色，测量它们的紫外-可见光谱以确定吸收最大值。完成了几个对照实验，证明单体之间的反应发生在胺和S 2 Cl 2之间，而不是亲电芳族取代反应。该聚合物在空气中稳定，但在 2-巯基乙醇存在下完全降解。在每一次降解中，二胺单体都被分离出来，环上没有任何硫醇的证据，正如亲电芳族取代所预期的那样。通过将这些聚合物暴露于 2-巯基乙醇并测量颜色变化，研究了它们作为 2-巯基乙醇传感器的能力。胺和 S 2 Cl 2之间的反应很快，可用于打印各种颜色的 2D 物体。
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