水溶性磺酸卟啉的合成、性质及光催化2,3-萘二酚
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摘要
制备了多种水溶性磺酸卟啉,利用多种测试手段如1H NMR,FTIR,UV-Vis及荧光等对该系列卟啉进行了表征及性质研究,测得荧光量子产率及寿命.利用不同氧源(空气、氧气、30%过氧化氢溶液)将该系列水溶性磺酸卟啉用于光催化氧化2,3-萘二酚的反应,反应产物是1,2-苯二甲酸,最高转化率可达91%.发现磺酸基和其它取代基的电子效应会影响卟啉的光催化活性.对该光催化氧化反应进行了动力学研究,并探讨了相应的催化机理.
A series of water-soluble sulfonated porphyrins have been synthesized and characterized by ~1H NMR, IR, UV-Vis, fluorescence and MS. The fluorescence quantum yield and lifetime of the series of porphyrins have been obtained. These porphyrins have been used as photocatalysts for the oxidation of 2,3-dihydroxynaphthalene. The main product has been proved to be 1,2-benzenedicarboxylic acid with the highest conversion rate of 91%. The effects of electron caused by different substituent groups and steric structure on sulfonated porphyrins photocatalytic activities have been investigated. It has been proved that substituent groups have electronic effects on the photocatalytic activities. The chosen of oxygen resource, the kinetics of the oxidation and the photocatalytic mechanism of sulfonated porphyrins have been investigated.
A series of water-soluble sulfonated porphyrins have been synthesized and characterized by ~1H NMR, IR, UV-Vis, fluorescence and MS. The fluorescence quantum yield and lifetime of the series of porphyrins have been obtained. These porphyrins have been used as photocatalysts for the oxidation of 2,3-dihydroxynaphthalene. The main product has been proved to be 1,2-benzenedicarboxylic acid with the highest conversion rate of 91%. The effects of electron caused by different substituent groups and steric structure on sulfonated porphyrins photocatalytic activities have been investigated. It has been proved that substituent groups have electronic effects on the photocatalytic activities. The chosen of oxygen resource, the kinetics of the oxidation and the photocatalytic mechanism of sulfonated porphyrins have been investigated.
引文
[1]Meunier,B.;de Visser,S.P.;Shaik,S.Chem.Rev.2004,104,3947.
[2](a)Castro,K.D.;Simoes,M.Q.;Neves,M.G.Catal.Sci.Technol.2014,4,129.(b)Haynes,D.A.;Laeren,L.J.V.;Munro,O.Q.J.Am.Chem.Soc.2017,139,14620.
[3](a)Lu,J.-M.;Cai,W.-Q.;Zhang G.-Z.Acta Chim.Sinica 2015,73,1153(in Chinese).(卢俊明,蔡万清,张桂传,化学学报,2015,73,1153.)(b)Shao,Q.-Y.;Yuan,X.-M.;Wang,X.-Y.Chin.J.Inorg.Chem.2016,32,1293(in Chinese).(沙秋月,袁雪梅,王小雨,无机化学学报,2016,32,1293.)(c)Zhao,S.-F.;Chen,N.-Y.;Guo,X.;Wang,M.-H.;Li,Z.-Y.Chin.J.Org.Chem.2010,30,1898(in Chinese).(赵胜芳,陈年友,郭鑫,王孟华,李早英,有机化学,2010,30,1898.)
[4]Sun,K.-F.;Guo,L.-T.;Cai,C.;Hou,Z.-S.;Ren,Q.-Z.ChemCat Chem 2017,9,4465.
[5](a)Pedrosa,L.F.;De Souza,M.C.;Faustino,M.A.F.;Neves,M.G.P.M.S.;Silva,A.M.S.;Tomé,A.C.Aust.J.Chem.2011,64,939.(b)Chang,Y.;Liu,M.-Y.;Niu,M.-Y.Chin.J.Org.Chem.2017,37,2442(in Chinese).(常毅,刘梦阳,牛梦园,有机化学,2017,37,2442.)(c)Ren,Q.-Z.;Yao,Y.;Ding,X.-J.;Hou,Z.-S.;Yan,D.-Y.Chem.Commun.2009,4732.(d)Liang,P.-X.;Mi,Y.-S.;Duan,J.-S.;Yang,Z.;Wang,D.;Cao,H.;He,W.-L.;Yang,H.Chin.J.Chem.2016,34,381.(e)To C.T.;Yang W.;Chan,K.S.Chin.J.Chem.2016,34,955.
[6]Cao,Y.;Gill,A.F.;Dixon,D.W.Tetrahedron Lett.2009,50,4358.
[7]Zhang,X.-X.;Chen,C.-Y.Acta Chim.Sinica 2012,70,2475(in Chinese).(张现侠,陈灿玉,化学学报,2012,70,2475.)
[8](a)Ren,Q.-G.;Zhou,X.-T.;Ji,B.-H.Chin.J.Org.Chem.2010,30,1605(in Chinese).(任清刚,周贤太,纪红兵,有机化学,2010,30,1605.)(b)Liu,Q.;Zhou,D.-D.;Li,Z.-X.;Luo,W.-P.;Guo,C.-C.Chin.J.Chem.2017,35,1063.
[9](a)Chang,L.-F.;Liu,Y.-Z.;Gao,J.Contemp.Chem.Ind.2011,40,85(in Chinese).(常凌飞,刘有智,高璟,当代化工,2011,40,85.)(b)Yao,Z.-P.;Chen,C.-J.;Wang,J.-K.Chin.J.Inorg.Chem.2017,33,1797(in Chinese).(姚忠平,陈昌举,王建康,无机化学学报,2017,33,1797.)
[10]K?pczyński,M.;Czosnyka,A.;Nowakowska,M.J.Photochem.Photobiol.A 2007,185,198.
[11](a)Hou,Z.-S.;Ren,Q.-Z.;Wang,Y.;Zhang,H.Chem.J.Chin.Univ.2011,32,2353(in Chinese).(侯宗胜,任奇志,王颖,章虹,高等学校化学学报,2011,32,2353.)(b)Ren,Q.-Z.;Hou,Z.-S.;Wang,Y.;Zhang,H.;Yang,S.Chem Sus Chem 2011,4,1063.(c)Wang,Y.;Ren,Q.-Z.;Guo,L.-T.;Hou,Z.-S.;Jiang,Z.-R.;Chem.J.Chin.Univ.2013,34,1576(in Chinese).(王颖,任奇志,郭琳童,侯宗胜,蒋宗润,高等学校化学学报,2013,34,1576.)
[12]Liu,S.-Y.;Ren,Q.-Z.;Ding,X.-J.Chem.J.Chin.Univ.2009,30,1272(in Chinese).(刘双艳,任奇志,丁晓健,高等学校化学学报,2009,30,1272.)
[13]Song,X.-F.;She,Y.-B.;Liu,R.;Sun,Z.-C.;Zhao,W.-B.Chem.Reagents 2011,33,193(in Chinese).(宋旭锋,佘远斌,刘燃,孙志成,赵文博,化学试剂,2011,33,193.)
[14]Fu,W.;Qian,K.-Y.;Luo,Y.Semicond.Optoelectron.2011,32,640(in Chinese).(付伟,钱可元,罗毅,半导体光电,2011,32,640.)
[15]Wu,Y.-Q.;Ouyang,R.-Z.Chin.J.Chem.Phys.1999,12,93(in Chinese).(吴谊群,欧阳瑞珍,化学物理学报,1999,12,93.)
[16]Zhang,Y.-W.;Shi,L.;Shen,H.Acta Opt.Sin.2008,28,2375(in Chinese).(张燕伟,史蕾,沈涵,光学学报,2008,28,2375.)
[17]Silva,E.;Pereira,M.M.;Burrows,H.D.;Azenha,M.E.;Sarakha,M.;Bolte,M.Photochem.Photobiol.Sci.2004,3,200.
[18]Cai,J.-H.Ph.D.Dissertation,Sun Yat-Sen University,Guangzhou,2009(in Chinese).(蔡金华,博士论文,中山大学,广州,2009.)
[19]Amat-Guerri,F.;Carrascoso,M.;Luiz,M.J.Photochem.Photobiol.A 1998,113,221.
[20]Zhang,H.-J.;Feng J.;Sun,Z.-Y.Chem.J.Chin.Univ.2003,24,2069(in Chinese).(张慧娟,冯娟,孙照勇,高等学校化学学报,2003,24,2069.)
[21]Cai,J.-H.;Huang,J.-W.;Zhao,P.;Zhou,Y.-H.;Yu,H.-C.;Ji,L.-N.J.Mol.Catal.A:Chem.2008,292,49.
[2](a)Castro,K.D.;Simoes,M.Q.;Neves,M.G.Catal.Sci.Technol.2014,4,129.(b)Haynes,D.A.;Laeren,L.J.V.;Munro,O.Q.J.Am.Chem.Soc.2017,139,14620.
[3](a)Lu,J.-M.;Cai,W.-Q.;Zhang G.-Z.Acta Chim.Sinica 2015,73,1153(in Chinese).(卢俊明,蔡万清,张桂传,化学学报,2015,73,1153.)(b)Shao,Q.-Y.;Yuan,X.-M.;Wang,X.-Y.Chin.J.Inorg.Chem.2016,32,1293(in Chinese).(沙秋月,袁雪梅,王小雨,无机化学学报,2016,32,1293.)(c)Zhao,S.-F.;Chen,N.-Y.;Guo,X.;Wang,M.-H.;Li,Z.-Y.Chin.J.Org.Chem.2010,30,1898(in Chinese).(赵胜芳,陈年友,郭鑫,王孟华,李早英,有机化学,2010,30,1898.)
[4]Sun,K.-F.;Guo,L.-T.;Cai,C.;Hou,Z.-S.;Ren,Q.-Z.ChemCat Chem 2017,9,4465.
[5](a)Pedrosa,L.F.;De Souza,M.C.;Faustino,M.A.F.;Neves,M.G.P.M.S.;Silva,A.M.S.;Tomé,A.C.Aust.J.Chem.2011,64,939.(b)Chang,Y.;Liu,M.-Y.;Niu,M.-Y.Chin.J.Org.Chem.2017,37,2442(in Chinese).(常毅,刘梦阳,牛梦园,有机化学,2017,37,2442.)(c)Ren,Q.-Z.;Yao,Y.;Ding,X.-J.;Hou,Z.-S.;Yan,D.-Y.Chem.Commun.2009,4732.(d)Liang,P.-X.;Mi,Y.-S.;Duan,J.-S.;Yang,Z.;Wang,D.;Cao,H.;He,W.-L.;Yang,H.Chin.J.Chem.2016,34,381.(e)To C.T.;Yang W.;Chan,K.S.Chin.J.Chem.2016,34,955.
[6]Cao,Y.;Gill,A.F.;Dixon,D.W.Tetrahedron Lett.2009,50,4358.
[7]Zhang,X.-X.;Chen,C.-Y.Acta Chim.Sinica 2012,70,2475(in Chinese).(张现侠,陈灿玉,化学学报,2012,70,2475.)
[8](a)Ren,Q.-G.;Zhou,X.-T.;Ji,B.-H.Chin.J.Org.Chem.2010,30,1605(in Chinese).(任清刚,周贤太,纪红兵,有机化学,2010,30,1605.)(b)Liu,Q.;Zhou,D.-D.;Li,Z.-X.;Luo,W.-P.;Guo,C.-C.Chin.J.Chem.2017,35,1063.
[9](a)Chang,L.-F.;Liu,Y.-Z.;Gao,J.Contemp.Chem.Ind.2011,40,85(in Chinese).(常凌飞,刘有智,高璟,当代化工,2011,40,85.)(b)Yao,Z.-P.;Chen,C.-J.;Wang,J.-K.Chin.J.Inorg.Chem.2017,33,1797(in Chinese).(姚忠平,陈昌举,王建康,无机化学学报,2017,33,1797.)
[10]K?pczyński,M.;Czosnyka,A.;Nowakowska,M.J.Photochem.Photobiol.A 2007,185,198.
[11](a)Hou,Z.-S.;Ren,Q.-Z.;Wang,Y.;Zhang,H.Chem.J.Chin.Univ.2011,32,2353(in Chinese).(侯宗胜,任奇志,王颖,章虹,高等学校化学学报,2011,32,2353.)(b)Ren,Q.-Z.;Hou,Z.-S.;Wang,Y.;Zhang,H.;Yang,S.Chem Sus Chem 2011,4,1063.(c)Wang,Y.;Ren,Q.-Z.;Guo,L.-T.;Hou,Z.-S.;Jiang,Z.-R.;Chem.J.Chin.Univ.2013,34,1576(in Chinese).(王颖,任奇志,郭琳童,侯宗胜,蒋宗润,高等学校化学学报,2013,34,1576.)
[12]Liu,S.-Y.;Ren,Q.-Z.;Ding,X.-J.Chem.J.Chin.Univ.2009,30,1272(in Chinese).(刘双艳,任奇志,丁晓健,高等学校化学学报,2009,30,1272.)
[13]Song,X.-F.;She,Y.-B.;Liu,R.;Sun,Z.-C.;Zhao,W.-B.Chem.Reagents 2011,33,193(in Chinese).(宋旭锋,佘远斌,刘燃,孙志成,赵文博,化学试剂,2011,33,193.)
[14]Fu,W.;Qian,K.-Y.;Luo,Y.Semicond.Optoelectron.2011,32,640(in Chinese).(付伟,钱可元,罗毅,半导体光电,2011,32,640.)
[15]Wu,Y.-Q.;Ouyang,R.-Z.Chin.J.Chem.Phys.1999,12,93(in Chinese).(吴谊群,欧阳瑞珍,化学物理学报,1999,12,93.)
[16]Zhang,Y.-W.;Shi,L.;Shen,H.Acta Opt.Sin.2008,28,2375(in Chinese).(张燕伟,史蕾,沈涵,光学学报,2008,28,2375.)
[17]Silva,E.;Pereira,M.M.;Burrows,H.D.;Azenha,M.E.;Sarakha,M.;Bolte,M.Photochem.Photobiol.Sci.2004,3,200.
[18]Cai,J.-H.Ph.D.Dissertation,Sun Yat-Sen University,Guangzhou,2009(in Chinese).(蔡金华,博士论文,中山大学,广州,2009.)
[19]Amat-Guerri,F.;Carrascoso,M.;Luiz,M.J.Photochem.Photobiol.A 1998,113,221.
[20]Zhang,H.-J.;Feng J.;Sun,Z.-Y.Chem.J.Chin.Univ.2003,24,2069(in Chinese).(张慧娟,冯娟,孙照勇,高等学校化学学报,2003,24,2069.)
[21]Cai,J.-H.;Huang,J.-W.;Zhao,P.;Zhou,Y.-H.;Yu,H.-C.;Ji,L.-N.J.Mol.Catal.A:Chem.2008,292,49.