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Cyanines comprising barbiturate group facilitate NIR-light assisted ATRP under anaerobic and aerobic conditions at two wavelengths using Fe(III) catalyst
Journal of Polymer Science ( IF 3.9 ) Pub Date : 2021-07-15 , DOI: 10.1002/pol.20210273 Ceren Kütahya 1 , Nicolai Meckbach 1 , Veronika Strehmel 1 , Bernd Strehmel 1
Journal of Polymer Science ( IF 3.9 ) Pub Date : 2021-07-15 , DOI: 10.1002/pol.20210273 Ceren Kütahya 1 , Nicolai Meckbach 1 , Veronika Strehmel 1 , Bernd Strehmel 1
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Cyanines with heptamethine pattern namely 5-(6-(2-(3-ethyl-1,1-dimethyl-1H-benzo[e]indol-2(3H)-ylidene)ethylidene)-2-(2-(3-ethyl-1,1-dimethyl-1H-benzo[e]indol-3-ium-2yl) vinyl) cyclo-hex-1-en-1-yl)-1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-olate comprising a barbiturate group facilitate controlled radical polymerization using FeBr3 in the ppm range applying radiation at 790 nm. Tris(4-methoylphenyl)phosphine, Tris(2-pyridylmethyl)amine or tetrabutylammonium bromide served as ligand. The latter showed the best performance resulting in a system needing no amino nitrogen for photo-ATRP. Ethyl α-bromophenylacetate worked as initiator. The cyanine interacts with FeBr3 resulting in a new absorption band at 877 nm that also resulted in formation of polymer exhibiting similar molecular weight but higher dispersity compared to that obtained by 790 nm radiation by exposure with a light-emitting diode (LED) emitting at 870 nm. This explains the reactivity of the system while other cyanines such as 2-[2-[3-[2-(1,3-Dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)-ethylidene]-2-(1-phenyl- 1H-tetrazol-5-ylsulfanyl)-1-cyclohexen-1-yl]-ethenyl]-1,3,3-trimethyl-3H-indolium chloride showed no activity by exposure at 790 nm in combination with FeBr3/Br−. Controlled radical polymerization was confirmed by successful chain extension and block copolymerization experiments resulting in polymers, which exhibit a dispersity of about 1.3. Interestingly, the new system comprising the aforementioned barbiturate substituted cyanine, FeBr3/Br− and ethyl α-bromophenylacetate showed a certain oxygen tolerance. Polymers obtained exhibited similar dispersity as those made under inert conditions.
中文翻译：
包含巴比妥酸盐基团的花青使用 Fe(III) 催化剂在厌氧和有氧条件下在两个波长下促进 NIR 光辅助 ATRP
具有七甲炔模式的花青，即 5-(6-(2-(3-ethyl-1,1-二甲基-1H-benzo[e]indol-2(3H)-ylidene)ethylidene)-2-(2-(3-乙基-1,1-二甲基-1H-苯并[e]吲哚-3-鎓-2基)乙烯基)环己-1-烯-1-基)-1,3-二甲基-2,6-dioxo-1包含巴比妥酸酯基团的,2,3,6-四氢嘧啶-4-醇酸酯促进受控自由基聚合，使用在 ppm 范围内施加 790 nm 辐射的FeBr 3。三(4-甲基苯基)膦、三(2-吡啶基甲基)胺或四丁基溴化铵作为配体。后者表现出最佳性能，导致系统不需要氨基氮用于光 ATRP。α-溴苯基乙酸乙酯作为引发剂。花青与 FeBr 3相互作用导致在 877 nm 处出现新的吸收带，与通过在 870 nm 处发射的发光二极管 (LED) 曝光而获得的 790 nm 辐射相比，这也导致形成的聚合物具有相似的分子量但具有更高的分散性。这解释了系统的反应性，而其他花青如 2-[2-[3-[2-(1,3-Dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)-ethylidene]- 2-(1-苯基-1H-四唑-5-基硫烷基)-1-环己烯-1-基]-乙烯基]-1,3,3-三甲基-3H-氯化吲哚在 790 nm 的组合下暴露无活性与 FeBr 3 /Br -. 受控自由基聚合通过成功的扩链和嵌段共聚实验得到证实，产生的聚合物的分散度约为 1.3。有趣的是，包含上述巴比妥酸盐取代花青、FeBr 3 /Br -和α-溴苯基乙酸乙酯的新体系显示出一定的氧耐受性。获得的聚合物表现出与在惰性条件下制备的聚合物相似的分散性。
更新日期：2021-09-15
中文翻译：
包含巴比妥酸盐基团的花青使用 Fe(III) 催化剂在厌氧和有氧条件下在两个波长下促进 NIR 光辅助 ATRP
具有七甲炔模式的花青，即 5-(6-(2-(3-ethyl-1,1-二甲基-1H-benzo[e]indol-2(3H)-ylidene)ethylidene)-2-(2-(3-乙基-1,1-二甲基-1H-苯并[e]吲哚-3-鎓-2基)乙烯基)环己-1-烯-1-基)-1,3-二甲基-2,6-dioxo-1包含巴比妥酸酯基团的,2,3,6-四氢嘧啶-4-醇酸酯促进受控自由基聚合，使用在 ppm 范围内施加 790 nm 辐射的FeBr 3。三(4-甲基苯基)膦、三(2-吡啶基甲基)胺或四丁基溴化铵作为配体。后者表现出最佳性能，导致系统不需要氨基氮用于光 ATRP。α-溴苯基乙酸乙酯作为引发剂。花青与 FeBr 3相互作用导致在 877 nm 处出现新的吸收带，与通过在 870 nm 处发射的发光二极管 (LED) 曝光而获得的 790 nm 辐射相比，这也导致形成的聚合物具有相似的分子量但具有更高的分散性。这解释了系统的反应性，而其他花青如 2-[2-[3-[2-(1,3-Dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)-ethylidene]- 2-(1-苯基-1H-四唑-5-基硫烷基)-1-环己烯-1-基]-乙烯基]-1,3,3-三甲基-3H-氯化吲哚在 790 nm 的组合下暴露无活性与 FeBr 3 /Br -. 受控自由基聚合通过成功的扩链和嵌段共聚实验得到证实，产生的聚合物的分散度约为 1.3。有趣的是，包含上述巴比妥酸盐取代花青、FeBr 3 /Br -和α-溴苯基乙酸乙酯的新体系显示出一定的氧耐受性。获得的聚合物表现出与在惰性条件下制备的聚合物相似的分散性。
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