锌卟啉功能化薄膜材料的制备与性能综合实验设计
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摘要
以吡咯、4-氯苯甲醛和醋酸锌等为原料,合成了一种取代四苯基卟啉锌的配合物,用元素分析、红外光谱、紫外-可见光谱和电喷雾质谱等手段表征了其组成和结构。采用静电纺丝法制备了聚丙烯腈(PAN)纤维为载体的含四苯基卟啉锌的配合物复合薄膜材料,研究了其荧光性能。该实验项目涵盖大环化合物的合成、柱色谱分离技术、静电纺丝技术和现代仪器分析技术等诸多知识点,具有综合性和可操作性,用于"现代化学化工实验技术"研究生课程的教学,可以培养研究生的综合实验技能和创新能力。
A substituted tetraphenyl-porphyrin zinc complex was prepared by using pyrrole,4-chlorobenzaldehyde,and acetic acid zinc as starting materials. The composition and structure of the complex were characterized by elemental analysis,infrared spectroscopy,ultraviolet-visible spectroscopy and electronic spray mass spectrometry. The composite film material with tetraphenyl-porphyrin zinc complex is prepared based on polyacrylonitrile( PAN) fiber as carrier by electrostatic spinning technology,and its fluorescence property was investigated. The experiment project covers many knowledge points such as synthesis of macrocyclic compounds, column chromatographic separation technology,electrostatic spinning technology and modern instrumental analysis techniques, and has the characteristics of comprehensiveness and operability. It is used in graduate course teaching for the modern chemical experiment technology to cultivate the graduate student's comprehensive experimental skill and innovation ability.
A substituted tetraphenyl-porphyrin zinc complex was prepared by using pyrrole,4-chlorobenzaldehyde,and acetic acid zinc as starting materials. The composition and structure of the complex were characterized by elemental analysis,infrared spectroscopy,ultraviolet-visible spectroscopy and electronic spray mass spectrometry. The composite film material with tetraphenyl-porphyrin zinc complex is prepared based on polyacrylonitrile( PAN) fiber as carrier by electrostatic spinning technology,and its fluorescence property was investigated. The experiment project covers many knowledge points such as synthesis of macrocyclic compounds, column chromatographic separation technology,electrostatic spinning technology and modern instrumental analysis techniques, and has the characteristics of comprehensiveness and operability. It is used in graduate course teaching for the modern chemical experiment technology to cultivate the graduate student's comprehensive experimental skill and innovation ability.
引文
[1]教育部.教育部、国家发展改革委、财政部关于深化研究生教育改革的意见[EB/OL].[2013-03-29]. http://www. moe. gov.cn/publicfiles/business/htmlfiles/moe/A22_zcwj/201307/xxgk_154118. html
[2]教育部.关于改进和加强研究生课程建设的意见[EB/OL].[2014-12-05]. http://www. moe. edu. cn/srcsite/A22/s7065/201412/t20141205_182992. html.
[3]教育部.教育部和国务院学位委员会关于印发《学位与研究生教育发展“十三五”规划》通知[EB/OL].[2017-01-17]. http://www. moe. gov. cn/srcsite/A22/s7065/201701/t20170120_295344.html.
[4]倪春林,周家容,杨卓鸿,等.农业院校研究生《现代化学化工实验技术》课程的设计与教学实践[J].化学教育,2018,39(6):61-65.
[5] Liu Y,Fu L Z,Yang L M,et al. The impact of modifying the ligands on hydrogen productionelectro-catalyzed by meso-tetra-p-Xphenylporphin cobaltcomplexes, CoT(X)PP[J]. Journal of Molecular Catalysis A:Chemical,2016,417(6):101-106.
[6] Peng Q X, Xue D, Zhan S Z, et al. Visible-light-driven photocatalytic system based on a nickel complex over CdS materials for hydrogen production from water[J]. Applied Catalysis B:Environmental. 2017,219(12):353-361.
[7] He T,Wang J N,Huang P L,et al. Electrospinning polyvinylidene fluoride fibrous membranescontaining antibacterial drugs used as wound dressing[J]. Colloids and Surfaces B:Biointerfaces,2015,130(6):278-286.
[8]杨乐敏,周武艺,倪春林,等.复合季鏻盐的制备、结构和抗菌性能实验的设计与教学实践[J].实验技术与管理,2016,33(5):209-211.
[9]倪春林,杨乐敏,周家容,等.农业院校研究生创新实验项目的设计与实践[J].实验室研究与探索,2017,36(1):169-172.
[10] Adler A D,Longo F R,Shergalis W. Mechanistic investigations of porphyrin syntheses. I. preliminary studies on ms-tetraphenylporphin[J]. Journal of the American Chemistry Society,1964,86(15):3145-3149.
[11] Luguya R,Jaquinod L,Fronczek F R,et al. Synthesis and reactions of meso-(p-nitrophenyl)porphyrins[J]. Tetrahedron,2004,60(12):2757-2763.
[12] Huang D K,Lu J F,Li,S H,et al. Fabrication of cobalt porphyrin. Electrochemically reduced graphene oxide hybrid films for electrocatalytic hydrogen evolution in aqueous solution[J].Langmuir,2014,30(23):6990-6998.
[13] Morgan R D,Derrick P J,Harrison A G. Direct Raman evidence for resonance interactions between the porphyrin ring system and ringconjugated substituents in porphyrins, porphyrin dications, and metalloporphyrins[J]. Journal of the American Chemistry Society,1977,99(12):4190-4192.
[14]赵瑶兴,孙祥玉.有机分子结构光谱鉴定[M]. 2版.北京:科学出版社,2010.
[15] Boucher L J,Katz J J. The infared spectra of metalloporphyrins(4000-160 cm-1)[J]. Journal of the American Chemistry Society,1967,89(6):1340-1345.
[16] Hariman A,Luminescence of porphyrins and metalloporphyrins. Part2.—Copper(II),chromium(III),manganese(III),iron(II)and iron(III)porphyrins[J]. Journal of the Chemical Society,Faraday Transactions I,1981,77(2):369-377.
[17] Lihitkar N B, Singh S B, Singh J. Optical investigations of interaction between zinc tetra phenyl porphyrin and CdSe nanoparticles[J]. Chemical Physics Letters,2009,483(4-6):227-232.
[2]教育部.关于改进和加强研究生课程建设的意见[EB/OL].[2014-12-05]. http://www. moe. edu. cn/srcsite/A22/s7065/201412/t20141205_182992. html.
[3]教育部.教育部和国务院学位委员会关于印发《学位与研究生教育发展“十三五”规划》通知[EB/OL].[2017-01-17]. http://www. moe. gov. cn/srcsite/A22/s7065/201701/t20170120_295344.html.
[4]倪春林,周家容,杨卓鸿,等.农业院校研究生《现代化学化工实验技术》课程的设计与教学实践[J].化学教育,2018,39(6):61-65.
[5] Liu Y,Fu L Z,Yang L M,et al. The impact of modifying the ligands on hydrogen productionelectro-catalyzed by meso-tetra-p-Xphenylporphin cobaltcomplexes, CoT(X)PP[J]. Journal of Molecular Catalysis A:Chemical,2016,417(6):101-106.
[6] Peng Q X, Xue D, Zhan S Z, et al. Visible-light-driven photocatalytic system based on a nickel complex over CdS materials for hydrogen production from water[J]. Applied Catalysis B:Environmental. 2017,219(12):353-361.
[7] He T,Wang J N,Huang P L,et al. Electrospinning polyvinylidene fluoride fibrous membranescontaining antibacterial drugs used as wound dressing[J]. Colloids and Surfaces B:Biointerfaces,2015,130(6):278-286.
[8]杨乐敏,周武艺,倪春林,等.复合季鏻盐的制备、结构和抗菌性能实验的设计与教学实践[J].实验技术与管理,2016,33(5):209-211.
[9]倪春林,杨乐敏,周家容,等.农业院校研究生创新实验项目的设计与实践[J].实验室研究与探索,2017,36(1):169-172.
[10] Adler A D,Longo F R,Shergalis W. Mechanistic investigations of porphyrin syntheses. I. preliminary studies on ms-tetraphenylporphin[J]. Journal of the American Chemistry Society,1964,86(15):3145-3149.
[11] Luguya R,Jaquinod L,Fronczek F R,et al. Synthesis and reactions of meso-(p-nitrophenyl)porphyrins[J]. Tetrahedron,2004,60(12):2757-2763.
[12] Huang D K,Lu J F,Li,S H,et al. Fabrication of cobalt porphyrin. Electrochemically reduced graphene oxide hybrid films for electrocatalytic hydrogen evolution in aqueous solution[J].Langmuir,2014,30(23):6990-6998.
[13] Morgan R D,Derrick P J,Harrison A G. Direct Raman evidence for resonance interactions between the porphyrin ring system and ringconjugated substituents in porphyrins, porphyrin dications, and metalloporphyrins[J]. Journal of the American Chemistry Society,1977,99(12):4190-4192.
[14]赵瑶兴,孙祥玉.有机分子结构光谱鉴定[M]. 2版.北京:科学出版社,2010.
[15] Boucher L J,Katz J J. The infared spectra of metalloporphyrins(4000-160 cm-1)[J]. Journal of the American Chemistry Society,1967,89(6):1340-1345.
[16] Hariman A,Luminescence of porphyrins and metalloporphyrins. Part2.—Copper(II),chromium(III),manganese(III),iron(II)and iron(III)porphyrins[J]. Journal of the Chemical Society,Faraday Transactions I,1981,77(2):369-377.
[17] Lihitkar N B, Singh S B, Singh J. Optical investigations of interaction between zinc tetra phenyl porphyrin and CdSe nanoparticles[J]. Chemical Physics Letters,2009,483(4-6):227-232.