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卟啉的疏水性和分子间π-π堆积作用使其光催化性能大幅降低。针对此,本文采用多元芳香酰氯化合物对多元氨基化卟啉(四氨基卟啉单体,TAPP)进行交联,合成出两种具有一定亲水性和互穿网络结构的新型芳香酰胺键联卟啉聚合物(均苯三甲酰胺键联卟啉聚合物,TAPP-TMC;对苯二甲酰胺卟啉聚合物,TAPP-TPC),以提高可见光催化性能。探究了其形貌、多孔结构及对可见光抗菌和染料降解等光催化性能的影响。结果表明:相对于TAPP,TAPP-TMC和TAPP-TPC聚合物均表现出更优异的可见光催化性能:大肠杆菌抑菌率分别是TAPP的2.5和2.6倍,金黄色葡萄球菌抑菌率分别是1.9和2.6倍;罗丹明B降解效率是4.2和5.6倍。同时,比较两种聚合物,具有较大孔容和比表面积的TAPP-TPC聚合物光催化性能更优。因此,芳香酰胺键的引入使卟啉聚合物具有一定亲水性、多孔结构和刚性基团,能有效提高卟啉的可见光催化性能。
Abstract：The hydrophobicity and intermolecular π-π stacking of porphyrin result in a decreased photocatalytic performance. In this study, we synthesized two novel aromatic amide-linked porphyrin-based polymers(triamide-linked porphyrin polymer, TAPP-TMC diamide-linked porphyrin polymer, TAPP-TPC) with a certain hydrophilicity and interpenetrating network structure. The porphyrin-based polymers were prepared via the cross-linking of polyaminoporphyrin(tetraaminoporphyrin monomer, TAPP) with multiple aromatic acyl chlorides. We investigated the effects of morphology, hydrophilicity and porosity of polymers on their visible photocatalytic performance including visible-light antibacterial and visible-light dye degradation. The results showed that both TAPP-TMC and TAPP-TPC polymers had higher photocatalytic performance than TAPP. The antibacterial efficiencies against E. coli were ～2.5 and ～2.6 times and those against S. aureus were 1.9 and 2.6 times higher than that of TAPP, respectively. The degradation rates of Rhodamine B were ～4.2 and ～5.6 times higher than that of TAPP, respectively. Meanwhile, results show that TAPP-TPC polymer with large pore volume and specific surface area had better photocatalytic performance than TAPP-TMC. Therefore, the introduction of aromatic amide bonds makes porphyrin polymers had a certain hydrophilicity, porous structure and rigid groups. This can effectively improve the visible-light photocatalytic performance of porphyrin.
[1] Hynek J,Zelenka J,Rathousky J,et al.Designing porphyrinic covalent organic frameworks for the photodynamic inactivation of bacteria[J].ACS Applied Materials & Interfaces,2018,10(10):8527-8535.
[2] 支永峰,马思,刘晓明.多孔有机聚合物非均相光催化研究进展[J].高分子通报,2018(6):160-171.Zhi Y F,Ma S,Liu X M.Progress of porous organic polymers in heterogeneous photocatalysis[J].Polymer Bulletin,2018(6):160-171.
[3] Ockwig N W,Delgado-Friedrichs O,O′Keeffe M,et al.Reticular chemistry:occurrence and taxonomy of nets and grammar for the design of frameworks[J].Accounts of Chemical Research,2005,38(3):176-182.
[4] 张婷婷,仝淑月,杨熙,等.卟啉金属有机框架材料在光催化领域的应用[J].精细化工,2019,36(8):1507-1512.Zhang T T,Gong S Y,Yang X,et al.Recent progress in application of porphyrin-based metal-organic framework materials in photocatalytic reactions[J].Fine Chemicals,2019,36(8):1507-1512.
[5] 刘兴燕,徐永港,熊成,等.卟啉金属有机骨架材料在光催化领域的研究进展[J].应用化工,2019,48(2):482-485.Liu X Y,Xu Y X,Xiong C,et al.Recent progress on the photocatalysis of porphyrin-based metal-organic frameworks[J].Applied Chemical Industry,2019,48(2):482-485.
[6] Ethirajan M,Chen Y,Joshi P,et al.The role of porphyrin chemistry in tumor imaging and photodynamic therapy[J].Chemical Society Reviews,2011,40(1):340-362.
[7] Jiang L,Gan C R R,Gao J,et al.A perspective on the trends and challenges facing porphyrin-based anti-microbial materials[J].Small,2016,12(27):3609-3644.
[8] Trachootham D,Alexandre J,Huang P.Targeting cancer cells by ROS-mediated mechanisms:A radical therapeutic approach?[J].Nature Reviews Drug Discovery,2009,8(7):579-591.
[9] 史婷婷,姬东方,于艳敏.卟啉聚集行为的研究进展[J].材料导报,2017,31(3):46-52.Shi T T,Ji D F,Yu Y M.Advances in porphyrin aggregation behavior[J].Materials Review,2017,31(3):46-52.
[10] Li B Q,Zhang S Y,Wang B,et al.A porphyrin covalent organic framework cathode for flexible Zn-air batteries[J].Energy & Environmental Science,2018,7(11):1723-1729.
[11] Li M T,Zhao H Y,Lu Z Y.Porphyrin-based porous organic polymer,Py-POP,as a multifunctional platform for efficient selective adsorption and photocatalytic degradation of cationic dyes[J].Microporous and Mesoporous Materials,2020,doi.org/10.101b/j.micromeso.2019.109774.
[12] 谢震,李玉森,陈龙,等.功能性共轭多孔聚合物材料[J].高分子学报,2016(12):1621-1634.Xie Z,Li Y S,Chen L,et al.Functional conjugated porous polymer materials[J].Acta Polymerica Sinica,2016(12):1621-1634.
[13] 万刚,付宇昂,郭佳宁,等.光电多孔共价有机材料的研究进展[J].化学学报,2015,73(6):557-578.Wan G,Fu Y A,Guo J N,et al.Photoelectronic porous covalent organic materials:Research progress and perspective[J].Acta Chimica Sinica,2015,73(6):557-578.
[14] Zhu W,Ding Z D,Wang X,et al.A three-dimensional porphyrin-based porous organic polymer with excellent biomimetic catalytic performance[J].Polymer Chemistry,2017,8:4327-4331.
[15] Li Y,Duan Q,Wang H,et al.Construction of two-dimensional porphyrin-based fully conjugated microporous polymers as highly efficient photocatalysts[J].Journal of Photochemistry and Photobiology A:Chemistry,2018,356(1):370-378
[16] Mukherjee G,Thote J,Aiyappa H B,et al.A porous porphyrin organic polymer (PPOP) for visible light triggered hydrogen production[J].Chemical Communications,2017,53(32):4461-4464.
[17] Yu Y,Li Y W,Li Y H,et al.A 1D porphyrin-based rigid conjugated polymer as efficient and recyclable visible-light driven photocatalyst[J].Reactive and Functional Polymers,2019,doi.org/10.101b/j.reacfunctpolym.2019.104340.
[18] Collman J P,Wang Z,Straumanis A.Isocyanate as a versatile synthon for modular synthesis of functionalized porphyrins[J].The Journal of Organic Chemistry,1998,63(8):2424-2425.
[19] 王岩,王海澍,许姝佳,等.对苯二甲酰氯桥连卟啉及其铜配合物的合成与光谱性质[J].大连工业大学学报,2008,27(4):313-315.Wang Y,Wang H S,Xu S J,et al.Synthesis and spectral characterization of a novel bridged-porphyrin dimer and its copper complex[J].Journal of Dalian Polytechnic University,2008,27(4):313-315.
[20] Duong P H H,Anjum D H,Peinemann K V,et al.Thin porphyrin composite membranes with enhanced organic solvent transport[J].Journal of Membrane Science,2018,563:684-693.
[21] 近藤精一,石川达雄,安部郁夫.吸附科学[M].北京:化学工业出版社,2006:32-35.Seiichi K,Ishikawa,Ikuo A.Adsorption Science[M].Beijing:Chemical Industry Press,2006:32-35.
[22] 琚宜文,姜波,侯泉林,等.华北南部构造煤纳米级孔隙结构演化特征及作用机理[J].地质学报,2005,79(2):269-285.Ju Y W,Jiang B,Hou Q L,et al.Structural evolution of nano-scale pores of tectonic coals in Southern North China and its mechanism[J].Acta Geologica Sinca,2005,79(2):269-285.
[23] 江兰兰,王先友,吴昊,等.炭化温度对金属有机基多孔碳结构和电化学性能的影响[J].中南大学学报(自然科学版),2013,44(10):4012-4018.Jiang L L,Wang X Y,Wu H,et al.Effect of carbonization temperature on structure and electrochemical performance of porous carbon from metal framework[J].Journal of Central South University (Science and Technology),2013,44(10):4012-4018.
基本信息:
DOI：10.16441/j.cnki.hdxb.20200023
中图分类号:TQ317
引用信息:
[1]徐佳,徐美庆,孙星,等.芳香酰胺键联卟啉聚合物的制备及其可见光催化性能研究[J],2020,50(S1):94-100.DOI:10.16441/j.cnki.hdxb.20200023.
基金信息:
中央高等基本科研务业专项(201841012);; 国家自然科学基金项目(21878279);; 山东省自然科学基金项目(ZR2018MB032)资助~~
2020-01-23
2020
2020-06-02
2020
2020-05-15
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