三环己基锡邻(二茂铁甲酰基)苯甲酸酯配位聚合物的微波固相合成、晶体结构及性能

doi:10.7503/cjcu20131282

高等学校化学学报 ›› 2014, Vol. 35 ›› Issue (8): 1629.doi: 10.7503/cjcu20131282

• 研究论文: 无机化学 • 上一篇下一篇

三环己基锡邻(二茂铁甲酰基)苯甲酸酯配位聚合物的微波固相合成、晶体结构及性能

邝代治(), 冯泳兰, 庾江喜, 张复兴, 蒋伍玖, 彭雁, 朱小明, 谭宇星

衡阳师范学院功能金属有机材料湖南省高校重点实验室, 化学与材料科学系, 衡阳 421008

收稿日期:2013-12-27 出版日期:2014-08-10 发布日期:2014-07-04
作者简介:联系人简介: 邝代治, 男, 教授, 主要从事金属有机合成研究. E-mail: hnkcq@qq.com
基金资助:
湖南省自然科学基金(批准号: 13JJ3112)、湖南省科技计划(批准号: 2013TZ2025)、湖南省高校创新平台开放基金(批准号: 13K105, 12K124)、衡阳市科技计划(批准号: 2012KJ30)、衡阳师范学院协同创新中心培育项目(批准号: 12XT02)和青年骨干教师培养计划(2012)资助

Microwave Assisted Solid-state Synthesis, Crystal Structure, Properties of the Coordination Polymer Constructed from Tricyclohexyltin Hydroxide and o-Ferrocenylcarbonyl Benzoic Acid^†

KUANG Daizhi^*(), FENG Yonglan, YU Jiangxi, ZHANG Fuxing, JIANG Wujiu, PENG Yan, ZHU Xiaoming, TAN Yuxing

Key Laboratory of Functional Organometallic Materials of College of Hunan Province, Department of Chemistry and Material Science, Hengyang Normal University, Hengyang 421008, China

Received:2013-12-27 Online:2014-08-10 Published:2014-07-04
Contact: KUANG Daizhi E-mail:hnkcq@qq.com
Supported by:
Supported by the Hunan Provincial Natural Science Foundation of China(No.13JJ3112), the Scientific & Technological Projects of Hunan Province, China(No.2013TZ2025), the Open Fund Based on Innovation Platform of Hunan Universities, China(Nos.13K105, 12K124), the Scientific & Technological Projects of Hengyang City, China(No.2012KJ30), the Cultivation Projects Based on Collaborative Innovation Center of Hengyang Normal University, China(No.12XT02) and the Youth Backbone Teacher Training Program of Hengyang Normal University, China(No.2012)

摘要/Abstract

摘要：

在微波辐射下, 邻二茂铁甲酰基苯甲酸与三环己基氢氧化锡反应, 合成了结构新颖的含铁锡多核配合物. 紫外光谱、红外光谱、核磁共振谱、元素分析和X射线晶体衍射表征结果表明, 配合物的中心锡与配基原子形成五配位畸变三角双锥构型, 通过配体的羧基氧和羰基氧原子分别与锡原子连接形成一维链配位聚合物. 热分析结果表明, 配合物在163 ℃以下具有较好的热稳定性. 其溶液在电极上能准可逆电子转移, 对人体细胞HT-29, MCF-7, HepG2, KB和A549的体外抗癌活性均高于对照药顺铂, 具有潜在应用价值.

关键词: 配位聚合物, 晶体结构, 电化学性质, 热稳定性, 抗癌活性

Abstract:

A novel coordination polymer tricyclohexyltin(o-ferrocenylcarbonyl) benzoate was synthesized by the reaction of tricyclohexyltin hydroxide with o-ferrocenylcarbonyl benzoic acid under microwave irradiation. It was characterized by UV, IR, ¹H and ¹³C NMR, elemental analysis and X-ray crystal diffraction. The crystal structure shows a distorted trigonal bipyramidal configuration with five-coordination for the central tin atom. The tin atoms and the oxygen atoms of C(O)—O and from the o-ferrocenylcarbonyl benzoate are interconnected to form a one-dimensional coordination polymer chain. The thermal studies showed that complex exhibited higher thermal stability. Electrochemical studies of the complex have been made in EtOH/H₂O by cyclic voltammetry. The complex shows quasi reversible electron transfer process. The in vitro antitumour activity of the complex was tested.The results show that the complex exhibits better antitumour activity in vitro against HT-29, MCF-7, HepG2, KB and A549 tumour cells. So the complex may have potential applications.

Key words: Coordination polymer, Crystal structure, Electrochemical property, Thermal stability, Anticancer activity

中图分类号:

O614.43⁺2

TrendMD:

邝代治, 冯泳兰, 庾江喜, 张复兴, 蒋伍玖, 彭雁, 朱小明, 谭宇星. 三环己基锡邻(二茂铁甲酰基)苯甲酸酯配位聚合物的微波固相合成、晶体结构及性能. 高等学校化学学报, 2014, 35(8): 1629.

KUANG Daizhi, FENG Yonglan, YU Jiangxi, ZHANG Fuxing, JIANG Wujiu, PENG Yan, ZHU Xiaoming, TAN Yuxing. Microwave Assisted Solid-state Synthesis, Crystal Structure, Properties of the Coordination Polymer Constructed from Tricyclohexyltin Hydroxide and o-Ferrocenylcarbonyl Benzoic Acid^†. Chem. J. Chinese Universities, 2014, 35(8): 1629.

图/表 5

Table 1 Selected bond lengths(nm) and bond angles(°) of the complex*

Sn1—C1	0.2155(4)	Sn1—C7	0.2146(4)	Sn1—C13	0.2159(4)
Sn1—O1^#	0.2126(2)	Sn1—O3	0.2651
O1^#—Sn1—C1	96.69(15)	O1^#—Sn1—C7	104.70(12)	O1^#—Sn1—C13	92.09(14)
C7—Sn1—C1	124.06(17)	C1—Sn1—C13	116.48(19)	C7—Sn1—C13	113.69(17)
O3—Sn1—C1	82.45	O3—Sn1—C7	83.35	O3—Sn1—C13	79.98
O1^#—Sn1—O3	170.53

Fig.1 Molecular structure of the complex H atoms are omitted for clarity. #: -x+2, y-1/2, -z+1/2.

Fig.2 1D polymeric structure of the complex Cyclohexyl groups are omitted for clarity.

Fig.3 2D supramolecular structure of the complex by C—H…π interactions C34#—H34#…π(C20—C25) 0.3555 nm, #: 1-x, 1-y, -z. Cyclohexyl groups are omitted for clarity.

Table 2 IC50 values of the complex and cis-platin on HepG2, KB, MCF-7, A549 and HT-29

Sample	IC₅₀/(μmol·L^-1)
Sample	HepG2	KB	MCF-7	A549	HT-29
Complex	0.298	0.935	0.293	1.008	0.079
cis-Platin	65.32	2.650	88.17	1.510	58.06

参考文献 31

[1]	Rahman M. M., Jusoh I., Affan M. A., Husaini A., Hamdan S., Eur. J. Wood Prod., 2013, 71(4), 463—471
[2]	Omae L., Appl. Organometal. Chem., 2003, 17(2), 81—105
[3]	Salam M. A., Affan M. A., Arafat M. A., Saha R., Nasrin R., Heteroatom Chemistry, 2013, 24(1), 43—52
[4]	Gong G. F., Song R., Zou Y. B., Lin S., Chinese J. Org. Chem., 2013, 33(4), 803—807
	(龚根飞, 宋冉, 邹引波, 林森. 有机化学, 2013, 33(4), 803—807)
[5]	Zhang X.X., Comparing of 30 Pesticides Sensitivity to Perennial Ryegrass and Strong Creeping Red Fescue, Gansu Agricultural University, Lanzhou, 2004(张绪校. 30种农药对多年生黑麦草和紫羊茅敏感性比较研究, 兰州: 甘肃农业大学, 2004)
[6]	Davies A.G., Gielen M., Pannell K. H., Tiekink E. R. T., Tin Chemistry, John Wiley & Sons, Chichester, 2008, 312—323
[7]	Chandrasekhar V., Thilagar P., Steiner A., Bickley J. F., Chem. Eur. J., 2006, 12(34), 8847—8861
[8]	Chandrasekhar V., Thirumoorthi R., Eur. J. Inorg. Chem., 2008, 2008(29), 4578—4585
[9]	Cervantes J., Zárraga R., Salazar-Hernández C., Appl. Organometal. Chem., 2012, 26(4), 157—163
[10]	Hussain M., Rehman Z., Hanif M., Altaf M., Rehman A., Ali S., Cavell K. J., Appl. Organometal. Chem., 2011, 25(6), 412—419
[11]	Dokorou V., Kovala-Demertzi D., Jasinski J. P., Galani A., Demertzis M. A., Helv. Chim. Acta., 2004, 87(8), 1940—1950
[12]	Kovala-Demertzi D., J. Organomet. Chem., 2006, 691(8), 1767—1774
[13]	Chandrasekhar V., Gopal K., Thilagar P., Acc. Chem. Res., 2007, 40(6), 420—434
[14]	Zhong G. Y., Sun L. J., Xie Q. L., Chem. J. Chinese Universities, 2010, 31(11), 2218—2221
	(钟桂云, 孙丽娟, 谢庆兰. 高等学校化学学报, 2010, 31(11), 2218—2221)
[15]	Chandrasekhar V., Baskar V., Gopal K., Vittal J. J., Organometallics, 2005, 24(21), 4926—4932
[16]	Chandrasekhar V., Thirumoorthi R., Organometallics, 2009, 28(7), 2096—2106
[17]	Li Q., Sun B. C., Song H. B., Tang L. F., Chem. J. Chinese Universities, 2013, 34(11), 2511—2516
	(李强, 孙宝川, 宋海斌, 唐良富. 高等学校化学学报, 2013, 34(11), 2511—2516)
[18]	Li Y. F., Li P. Z., Liu Z. Q., Chem. Res. Chinese Universities, 2013, 29(5), 947—951
[19]	Chandrasekhar V., Thirumoorthi R., Organometallics, 2007, 26(22), 5415—5422
[20]	Peng B., Sun L. J., Chang W. X., Xie Q. L., Chinese J. Org. Chem., 2003, 23(4), 344—349
	(彭斌, 孙丽娟, 常卫星, 谢庆兰. 有机化学,, 2003, 23(4), 344—349)
[21]	Wang J. Q., Kuang D. Z., Zeng R. Y., Zhang F. X., Feng Y. L., Chen Z. M., Chinese J. Struct. Chem., 2007, 26(6), 674—678
[22]	Kuang D. Z., Chen Z. M., Zhang F. X., Wang J. Q., Feng Y. L., Chinese J. Inorg. Chem., 2006, 22(11), 1947—1951
	(邝代治, 陈志敏, 张复兴, 王剑秋, 冯泳兰. 无机化学学报, 2006, 22(11), 1947—1951)
[23]	Singh R. V., Chaudhary P., Poonia K., Chauhan S., Spectrochimica Acta Part A, 2008, 70(3), 587—594
[24]	Murugavel R., Gogoi N., J. Organomet. Chem., 2008, 693(19), 3111—3116
[25]	Li Z. F., Liu S. M., Wu J. X., Li G., Chem. Res., 2008, 19(2), 51—54
	(李志峰, 刘淑敏, 吴静霞, 李纲. 化学研究, 2008, 19(2), 51—54)
[26]	Nesmeyanov A. N., Vol’kenau N. A., Vil’chevskaya V. D., Doklady Akademii Nauk SSSR, 1956, 111, 362—364
[27]	Zuo C.Y., Synthesis, Characterization and Properties of Ferrocenyl Derivatives, Anhui University, Hefei, 2004
	(左从玉. 二茂铁衍生物的合成、表征及其性质研究, 合肥: 安徽大学, 2004)
[28]	Ke Y.K., Dong H. R., Analysis Chemistry Handbook, Vol.3: Spectral Analysis, Chemical Industry Press, Beijing, 1998, 1188—1189
	(柯以侃, 董慧茹. 分析化学手册第三分册: 光谱分析, 北京: 化学工业出版社, 1998, 1188—1189)
[29]	Ke Y.K., Dong H. R., Analysis Chemistry Handbook, Vol.3: Spectral Analysis, Chemical Industry Press, Beijing, 1998, 932—935
	(柯以侃, 董慧茹. 分析化学手册第三分册: 光谱分析, 北京: 化学工业出版社, 1998, 932—935)
[30]	Xie Q. L., Xu X. H., Zhang D. K., Acta Chim. Sinica, 1992, 50, 508—514(谢庆兰, 徐效华, 张殿坤. 化学学报, 1992,50, 508—514)
[31]	Peng T.Z., Wang G. S., Analysis Chemistry Handbook, Vol.4: Electroanalytical Chemistry, Chemical Industry Press, Beijing, 1999, 483—484
	(彭图治, 王国顺. 分析化学手册第四分册: 电分析化学, 北京: 化学工业出版社, 1999, 483—484)
	(Ed.: P, H, V, K)

三环己基锡邻(二茂铁甲酰基)苯甲酸酯配位聚合物的微波固相合成、晶体结构及性能

Microwave Assisted Solid-state Synthesis, Crystal Structure, Properties of the Coordination Polymer Constructed from Tricyclohexyltin Hydroxide and o-Ferrocenylcarbonyl Benzoic Acid^†

RichHTML

PDF (PC)

可视化

被引次数

摘要/Abstract

引用本文

使用本文

图/表 5

参考文献 31

相关文章 15

编辑推荐

Metrics

本文评价

[1]	施耐克, 张娅, SANSON Andrea, 王蕾, 陈骏. Zn(NCN)单轴的负热膨胀性及机理研究[J]. 高等学校化学学报, 2022, 43(6): 20220124.
[2]	常斯惠, 陈涛, 赵黎明, 邱勇隽. 离子液体增塑生物基聚丁内酰胺的热分解机理[J]. 高等学校化学学报, 2022, 43(11): 20220353.
[3]	马鉴新, 刘晓东, 徐娜, 刘国成, 王秀丽. 一种具有发光传感、安培传感和染料吸附性能的多功能Zn(II)配位聚合物[J]. 高等学校化学学报, 2022, 43(1): 20210585.
[4]	赵莹, 乔玲, 赵国锋, 陈莉. 含苹果酸酯的石蒜碱衍生物的合成及生物活性[J]. 高等学校化学学报, 2021, 42(9): 2789.
[5]	岳胜利, 武光宝, 李星, 李康, 黄高胜, 唐翌, 周惠琼. 准二维钙钛矿太阳能电池的研究进展[J]. 高等学校化学学报, 2021, 42(6): 1648.
[6]	段军, 周萍萍, 张立倩, 马琳, 喻文, 朱美琦, 庄敏艳, 杨凤磊, 曹昌盛, 张鹏, 史延慧. 咪唑配位的半三明治钌金属(Ⅱ)大环化合物的合成及抗癌活性[J]. 高等学校化学学报, 2021, 42(12): 3589.
[7]	张俊, 王彬, 潘莉, 马哲, 李悦生. 含咪唑离子聚乙烯离聚体的合成与性能[J]. 高等学校化学学报, 2020, 41(9): 2070.
[8]	田霞,杨福群,袁伟,赵雷,姚雷,甄小丽,韩建荣,刘守信. 含噁二唑大环冠醚的合成、结构及金属离子识别性能[J]. 高等学校化学学报, 2020, 41(3): 490.
[9]	刘东枚,苏雅静,李姗姗,许奇炜,李夏. 4-(4-羧基苯氧基)间苯二甲酸构筑的过渡金属配位聚合物: 合成、晶体结构、荧光传感与光催化[J]. 高等学校化学学报, 2020, 41(2): 253.
[10]	咸国轩, 于玉娥, 陈玉倩, 万小雨, 王素娜, 卢静. 辅助配体调控的荧光Cd-MOFs: 乙酰丙酮的荧光增强和Cr(Ⅵ)的荧光猝灭[J]. 高等学校化学学报, 2020, 41(12): 2725.
[11]	秦刘磊,刘洋,关小琴,郑晓媛,张子钰,刘尊奇. 无机-有机杂化化合物[(H₂DABCO)CuCl₄]·H₂O的合成及开关型介电性质[J]. 高等学校化学学报, 2020, 41(1): 70.
[12]	冉诗雅, 沈海峰, 李晓楠, 王子路, 郭正虹, 方征平. 三氟甲烷磺酸稀土盐对聚丙烯热稳定性的影响及机理[J]. 高等学校化学学报, 2019, 40(6): 1333.
[13]	房夕杰, 刘瑞云, 林森, 石磊, 王润伟, 李乙, 李俊英. 蒸汽辅助合成STW结构硅锗酸盐分子筛[J]. 高等学校化学学报, 2019, 40(5): 867.
[14]	李冰, 王学敏, 白凤英, 刘淑清. 稀土氮杂环配合物的合成、结构及抑菌活性[J]. 高等学校化学学报, 2019, 40(4): 632.
[15]	刘韬, 李文静, 张恩爽, 钟锦洋, 张凡, 刘圆圆, 赵英民. 柔性交联型聚酰亚胺气凝胶的制备及性能[J]. 高等学校化学学报, 2019, 40(2): 403.

三环己基锡邻(二茂铁甲酰基)苯甲酸酯配位聚合物的微波固相合成、晶体结构及性能

Microwave Assisted Solid-state Synthesis, Crystal Structure, Properties of the Coordination Polymer Constructed from Tricyclohexyltin Hydroxide and o-Ferrocenylcarbonyl Benzoic Acid†

RichHTML

PDF (PC)

可视化

被引次数

摘要/Abstract

引用本文

使用本文

图/表 5

参考文献 31

相关文章 15

编辑推荐

Metrics

本文评价

Microwave Assisted Solid-state Synthesis, Crystal Structure, Properties of the Coordination Polymer Constructed from Tricyclohexyltin Hydroxide and o-Ferrocenylcarbonyl Benzoic Acid^†