羟基咔咯镓(Ⅲ)的合成及荧光性质研究
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摘要
以10-(4-羟基苯基)-5,15-二(2,3,4,5,6-五氟苯基)咔咯为母体,和GaCl_3进行反应得到10-(4-羟基苯基)-5,15-二(2,3,4,5,6-五氟苯基)咔咯镓配合物,产率为80%.采用核磁共振氢谱、质谱、紫外可见光谱对化合物进行表征.通过测定两种化合物的稳态吸收光谱和稳态荧光光谱,研究它们的光谱性质.结果表明:在浓度相同时,引入金属镓能够显著增加咔咯的吸收强度和荧光量子产率.
A novel 10-(4-hydroxyphenyl)-5,15-bis(2,3,4,5,6-pentafluorophenyl)corrole gallium was synthesized by reaction of 10-(4-hydroxyphenyl)-5,15-bis(2,3,4,5,6-pentafluorophenyl)corrole with GaCl_3 with a yield of 80% was synthesized and characterized by ~1H-NMR, HR-MS and UV-vis. The luminescence properties of these compounds were studied by steady-state absorption and fluorescent spectroscopy. Results revealed that the introduction of gallium can increase the absorption intensity, fluorescence intensity and fluorescence quantum yield compared to its free base.
A novel 10-(4-hydroxyphenyl)-5,15-bis(2,3,4,5,6-pentafluorophenyl)corrole gallium was synthesized by reaction of 10-(4-hydroxyphenyl)-5,15-bis(2,3,4,5,6-pentafluorophenyl)corrole with GaCl_3 with a yield of 80% was synthesized and characterized by ~1H-NMR, HR-MS and UV-vis. The luminescence properties of these compounds were studied by steady-state absorption and fluorescent spectroscopy. Results revealed that the introduction of gallium can increase the absorption intensity, fluorescence intensity and fluorescence quantum yield compared to its free base.
引文
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[2] HE C L,REN F L,ZHANG X B,et al.A fluorescent chemical sensor for Hg(II) based on a corrole derivative in a PVC matrix[J].Talanta,2006,70(2):364-369.
[3] AVIV-HAREL I,GROSS Z.Aura of corroles[J].Chemistry,2009,15(34):8382-8394.
[4] 邹怀波,汪华华,梅光泉,等.铁咔咯配合物在有机合成中的催化应用[J].化学进展,2015,27(6):666-674.
[5] FLAMIGNI L,VENTURA B,TASIOR M.Photophysical properties of a new,stable corrole-porphyrin dyad[J].Inorganica Chimica Acta,2007,360(3):803-813.
[6] SIMKHOVICH L,GROSS Z.Iron(IV) corroles are potent catalysts for aziridination of olefins by Chloramine-T[J].Tetrahedron Lett,2001,42(45):8089-8092.
[7] 刘杰,许东晖,梅文杰,等.水溶性卟啉及其系列金属化合物的合成、抗癌活性及其作用机制研究[J].高等学校化学学报,2001,22(9):1446-1449.
[8] ROMERA C,SABATER L,GAROFALO A,et al.Interaction of Cationic Nickel and Manganese Porphyrins with the Minor Groove of DNA [J].Inorganic Chemistry,2010,49(18):8558-8567.
[9] ETHIRAJAN M,CHEN Y H,JOSHIA P,et al.The role of porphyrin chemistry in tumor imaging and photodynamic therapy[J].Chemical Society Reviews,2011,40(1):340-362.
[10] CHENG F,WANG H H,ALI A,et al.Photophysical properties and photodynamic anti-tumor activity of corrole-coumarin dyads[J].Journal of Porphyrins and Phthalocyanines,2018,22:886-898.
[11] BENDIX J,DMOCHOWSKI I J,GRAY H B,et al.Structual,Electrochemical,and Photophysical Properities of Gallium (Ⅲ) 5,10,15 Tri(pentafluorophenyl)corrole[J].Angewandte Chemie International Edition,2000,39(22):4048-4051.
[12] 黄俊腾,张阳,王湘利,等.磺酸咔咯及其镓(Ⅲ)配合物与DNA的相互作用和光核酸酶活性[J].无机化学学报,2013(8):1649-1656.
[13] 陆俊,王湘利,陈伟健,等.水溶性镓Corrole配合物的制备及其对DNA的光断裂作用[J].合成化学,2010,18(S1):165-169.
[14] JIA M W,YUAN Li,HUI Q Y,DAN H W,et al.Methyl Benzoate Gallium(Ⅲ) corrole complexes:DNA-binding,Photocleavage Activity,Cytotoxicity on Tumor Cells[J].Applied Organometallic Chemistry,2017,31(3):1-12.
[15] AGADJANIAN H,MA J,RENTSENDORJ A,et al.Tumor detection and elimination by a targeted gallium corrole [J].Proceedings of the National Academy of Sciences of the United States of America,2009,106(15):6105-6110.
[16] HWANG J Y,GROSS Z,GRAY H B,et al.Ratiometric spectral imaging for fast tumor detection and chemotherapy monitoring in vivo[J].Journal Biomedical Optics,2011,16(6):0660071-0660076.
[17] YE Z,LIANG Y,MA Y,et al.Targeted photodynamic therapy of cancer using a novel gallium (Ⅲ) tris (ethoxycarbonyl) corrole conjugated-mAb directed against cancer/testis antigens 83[J].Cancer medicine.2018.
[18] ZHANG Z,WANG H H,YU H J,et al.Synthesis,characterization and in vitro and in vivo photodynamic activities of a gallium(iii) tris(ethoxycarbonyl)corrole[J].Dalton Trans,2017,46:9481-9490.
[19] SANTOS C M,OLIVEIRA E,BARATA J B,et al.New gallium(Ⅲ) corrole complexes as colorimetric probes for toxic cyanide anion[J].Inorganica Chimica Acta,2014,417:148-54.
[20] 何婧,徐志广,曾允秀,等.取代基对咔咯锰(V)-氧配合物Mn-O的成键影响[J].物理化学学报,2012,28(7):1658-1664.
[21] 陈华彬,章小慧,龚丽珍,等.β位取代基对咔咯锰(Ⅴ)氧配合物电子吸收光谱的影响[J].物理化学学报,2016,32(8):1983-1989.
[22] CHANG C K,KONG P W,LIU H Y,et al.Synthesis and Photodynamic Activities of Modified Corrole Derivatives on Nasopharyngeal Carcinoma Cells[J].Proceedings of SPIE,2006,6139,613915-1.
[23] LIU H Y,LIU L Y,ZHANG L,et al.Oxidative DNA cleavage catalyzed by Mn(Ⅲ)corrole[J].Chem J Chinese Universities,2007,28:1628-1630.
[24] 史蕾,江焕峰,尹伟,等.吩噻嗪-Corrole镓(Ⅲ)配合物的合成、荧光及其光断裂DNA性质(英文)[J].物理化学学报,2012,28(2):465-469.
[25] 杨洗,潘祖亭,马勇.用罗丹明B作标准物测定二氯荧光素的荧光量子产率[J].分析科学学报,2003(6):588-589.
[26] 樊美公.光化学基本原理与光子学材料科学[M].北京:科学出版社,2001.
[27] 何霜,陈欢,张松金,等.铝镓咔咯配合物的发光性质、堆积效应与轴向配位作用[J].无机化学学报,2013(1):26-34.