Synthesis and Dyes Complexation of Calix[4]arene Derivatives with Azo-macrocyclic Cavities

doi:10.6023/cjoc201308028

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (2): 424-428.DOI: 10.6023/cjoc201308028 Previous Articles Next Articles

Notes

具氮杂大环空腔的杯[4]衍生物的合成与染料分子配合性能

洪碧琼^a,b, 杨发福^a,c, 郭红玉^a, 刘志强^a

a 福建师范大学化学与化工学院福州 350007;
b 武警福州指挥学院福州 350002;
c 福建省高分子材料重点实验室福州 350007

收稿日期:2013-08-21 修回日期:2013-10-07 发布日期:2013-10-11
通讯作者: 杨发福 E-mail:yangfafu@fjnu.edu.cn
基金资助:
福建省高校科技创新团队支持计划（闽教科[2012]03号）、福建省高校杰出青年科研人才培育计划（No.JA10056）和福建省教育厅重点（No.JA11044）资助项目.

Synthesis and Dyes Complexation of Calix[4]arene Derivatives with Azo-macrocyclic Cavities

Hong Biqiong^a,b, Yang Fafu^a,c, Guo Hongyu^a, Liu Zhiqiang^a

a College of Chemistry and Materials, Fujian Normal University, Fuzhou 350007;
b Fuzhou Command Academy of Armed Police Force, Fuzhou 350002;
c Fujian Key Laboratory of Polymer Materials, Fuzhou 350007

Received:2013-08-21 Revised:2013-10-07 Published:2013-10-11
Supported by:
Project supported by the Program for Innovative Research Team in Science and Technology in Fujian Province University (No. [2012]03), the Program for Excellent Young Researchers in University of Fujian Province (No. JA10056), and the Project of Fujian Provincial Department of Education (No. JA11044).

Calix[4]arene hydrazide derivative 4 was obtained by reacting calix[4]-1,3-bis-ester derivative 3 with hydrazine. Then reacting compound 4 with hexamethylene diisocyanate or long aliphatic bis-aldehyde derivative 2 in “1+1” condensation mode, two novel calix[4]arene derivatives 5 and 6 with azo-macrocyclic cavity were obtained in yields of 85% and 80%, respectively. The liquid-liquid two phase extraction experiments showed that the extraction percentages of compounds 5 and 6 for orange I and methylene blue were more than 80%. The experiments of UV titration spectra suggested that they exhibited good complexation abilities for dyes with 1:1 ratios for complexation and 10⁴ magnitudes for the association constants.

Key words: calix[4]arene, azo-macrocyclic, synthesis, dye, complexation

Cite this article

Hong Biqiong, Yang Fafu, Guo Hongyu, Liu Zhiqiang. Synthesis and Dyes Complexation of Calix[4]arene Derivatives with Azo-macrocyclic Cavities[J]. Chin. J. Org. Chem., 2014, 34(2): 424-428.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Sliwa, W.; Kozlowski, C. Calixarenes and Resorcinarenes, Wiley-VCH, Weinheim, 2009.

[2] Joseph, R.; Rao C. P. Chem. Rev. 2011, 111, 4658.

[3] Zhang, Y.; Yang, F.; Bai, X.; Liu, Z.; Guo, H. Chin. J. Org. Chem. 2012, 32, 2350 (in Chinese).

(张瑛美, 杨发福, 白小艳, 刘志强, 郭红玉, 有机化学, 2012, 32, 2350.)

[4] Ye, J.; Yang, F.; Zhang, X.; Jiao, Z.; Guo, H. Chin. J. Org. Chem. 2012, 32, 189 (in Chinese).

(叶进启, 杨发福, 张筱逸, 焦自玉, 郭红玉, 有机化学, 2012, 32, 189.)

[5] Xu, B.; Yang, F.; Liu, Z.; Chai, X.; Guo, H. Chin. J. Org. Chem. 2011, 31, 737 (in Chinese).

(许冰婷, 杨发福, 刘志强, 柴先锋, 郭红玉, 有机化学, 2011, 31, 737.)

[6] Yang, F.; Wang, Y.; Guo, H.; Xie, J.; Liu, Z. Can. J. Chem. 2010, 88, 622.

[7] Yang, F.; Huang, Z.; Guo. Y.; Hong, B.; Zhang, X. J. Inclusion Phenom. Macrocyclic Chem. 2011, 70, 11.

[8] Yang, F.; Jiao, Z.; Huang, Z.; Xie, J.; Guo, H. J. Inclusion Phenom. Macrocyclic Chem. 2012, 74, 257.

[9] Sang, Q.; Yan, J. Chin. J. Chem. 2012, 30, 1410.

[10] Wong, Y.; Yu, J. Water Res. 1999, 33, 3512.

[11] Crini, G. Prog. Polym. Sci. 2005, 30, 38.

[12] Akceylan, E.; Bahadir, M.; Yilmaz, M. J. Hazard. Mater. 1999, 162, 960.

[13] Yilmaz, E. O.; Sirit, A.; Yilmaz, M. J. Macromol. Sci., Part A: Pure Appl. Chem. 2007, 44, 167.

[14] Yilmaz, A.; Yilmaz, E.; Yilmaz, M. Dyes Pigm. 2007, 74, 54.

[15] Kamboh, M.; Solangi, I.; Sherazi, S. Desalination 2011, 268, 83.

[16] Kamboh, M.; Solangi, I.; Memon, S. J. Hazard. Mater. 2011, 186, 651.

[17] Bai, X.; Yang, F.; Xie, J.; Guo, H. J. Macromol. Sci., Part A: Pure Appl. Chem. 2013, 50, 334.

[18] Yang, F.; Liu, W.; Xie, J.; Bai, X.; Guo, H. J. Inclusion Phenom. Macrocyclic Chem. 2013, 76, 311.

[19] Connors, K. Binding Constants, Wiley, New York, 1987.

[20] Yang, F.; Zheng, L.; Ji, Y.; Guo, H.; Lin, J. Chin. J. Org. Chem. 2006, 26, 268 (in Chinese).

(杨发福, 郑林禄, 季衍卿, 郭红玉, 林建荣, 有机化学, 2006, 26, 268.)

具氮杂大环空腔的杯[4]衍生物的合成与染料分子配合性能

Synthesis and Dyes Complexation of Calix[4]arene Derivatives with Azo-macrocyclic Cavities

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Penghui Li, Qingyang Xie, Fuxian Wan, Yuanhong Zhang, Lin Jiang. Synthesis and Fungicidal Activity of Novel Substituted Pyrimidine-5-carboxamides Bearing Cyclopropyl Moiety [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 650-656.
[2]	Fakai Zou, Nengzhong Wang, Hui Yao, Hui Wang, Mingguo Liu, Nianyu Huang. Regio- and Stereo-selective Synthesis of 1β-/3R-Aryl Thiosugar [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 593-604.
[3]	Luyao Li, Zhongwen He, Zhenguo Zhang, Zhenhua Jia, Teck-Peng Loh. Application of Triaryl Carbenium in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 421-437.
[4]	Qinggang Mei, Qinghan Li. Recent Progress of Visible Light-Induced the Synthesis of C(3) (Hetero)arylthio Indole Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 398-408.
[5]	Shihang Yu, Jiawei Liu, Biyu An, Qinghua Bian, Min Wang, Jiangchun Zhong. Asymmetric Synthesis of the Contact Sex Pheromone of Neoclytus acuminatus acuminatus (Fabricius) [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 301-308.
[6]	Weiqing Yang, Yanbing Ge, Yuanyuan Chen, Ping Liu, Haiyan Fu, Menglin Ma. Design and Synthesis of Fluorescent 1,8-Napthalimide Derivatives and Their Identification of Cysteine [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 180-194.
[7]	Qianfan Zhao, Yongzheng Chen, Shiming Zhang. Application and Mechanism Study of Carbon-Based Metal-Free Catalysts in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 137-147.
[8]	Shan Chen, Zhilin Chen, Qiong Hu, Yanshuang Meng, Yue Huang, Pingfang Tao, Liru Lu, Guobao Huang. Recognition of Bis-thiourea Tweezers to Neutral Molecules in Non-Polar Solvent [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 277-281.
[9]	Huakun Wang, Xiaolong Ren, Yining Xuan. Study of the Halide Salt Catalyzed [3＋2] Cycloaddition of α,β-Epoxy Carboxylate with Isocyanate [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 251-258.
[10]	Yukun Jin, Baoyi Ren, Fushun Liang. Visible Light-Mediated Selective C—F Bond Cleavage of Trifluoromethyl Groups and Its Application in Synthesizing gem-Difluoro-Containing Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 85-110.
[11]	Cuiyun Ma, Hailan Luo, Fuhua Zhang, Dan Guo, Shuxing Chen, Fei Wang. Green Biosynthesis, Photophysical Properties and Application of 3-Pyrrolyl BODIPY [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 216-223.
[12]	Bozhen Wang, Jie Zhang, Chunhui Nian, Mingming Jin, Miaomiao Kong, Wulan Li, Wenfei He, Jianzhang Wu. Synthesis and Antitumor Activity of 3,4-Dichlorophenyl Amides [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 232-241.
[13]	Ruixia Cao, Yuping Jia. Synthesis and Biological Activity of Novel Pyrrolo[2,3-d]pyrimidine Derivatives Containing Coumarin [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3304-3311.
[14]	Huanqing Li, Zhaohua Chen, Zujia Chen, Qiwen Qiu, Youcai Zhang, Sihong Chen, Zhaoyang Wang. Research Progress in Mercury Ion Fluorescence Probes Based on Organic Small Molecules [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3067-3077.
[15]	Ran Zhou, Chunmei Yuan, Tao Zhang, Piao Mao, Yi Liu, Kaini Meng, Hui Xin, Wei Xue. Design, Synthesis and Bioactivity of Chalcone Derivative Containing Quinazolinone [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3196-3209.