One-Pot Synthesis of A New [2]rotaxane Based on the Phenylene-Diacetylene Crown Ether

doi:10.6023/cjoc201406009

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (12): 2559-2565.DOI: 10.6023/cjoc201406009 Previous Articles Next Articles

Notes

一锅法合成基于丁二炔-苯环冠醚的[2]轮烷

陈木娟, 郭浩玉, 周松根, 陈坤, 蒋腊生

华南师范大学化学与环境学院广州 510006

收稿日期:2014-06-07 修回日期:2014-07-19 发布日期:2014-08-11
通讯作者: 蒋腊生 E-mail:jianglsh@scnu.edu.cn
基金资助:
国家自然科学基金(No.21072066)和广东省省部产学研基金(No.2012B090700003)资助项目.

One-Pot Synthesis of A New [2]rotaxane Based on the Phenylene-Diacetylene Crown Ether

Chen Mujuan, Guo Haoyu, Zhou Songgen, Chen Kun, Jiang Lasheng

School of Chemistry and Environment, South China Normal University, Guangzhou 510006

Received:2014-06-07 Revised:2014-07-19 Published:2014-08-11
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21072066) and the Key Project on the Integration of Industry, Education and Research of Guangdong Province (No. 2012B090700003).

A new [2]rotaxane was synthesized via one-pot method, based on the assembly of the phenylene-diacetylene crown ether (acted as ring molecule) and the paraquat derivative (acted as semi-axle molecule). The HR-MS, ¹H NMR and ¹³C NMR spectra have confirmed that one phenylene-diacetylene crown ether ring threaded though the axle molecule forming the corresponding [2]rotaxane, and the macrocyclic ring moves from one 4,4'-bipyridinium station to another 4,4'-bipyridinium station.

Key words: phenylene-diacetylene crown ether, one-pot method, synthesis, [2]rotaxane

Cite this article

Chen Mujuan, Guo Haoyu, Zhou Songgen, Chen Kun, Jiang Lasheng. One-Pot Synthesis of A New [2]rotaxane Based on the Phenylene-Diacetylene Crown Ether[J]. Chin. J. Org. Chem., 2014, 34(12): 2559-2565.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Schalley, C. A.; Beizai, K.; Vogtle F. Acc. Chem. Res. 2001, 34, 465. (b) Collier, C. P.; Wong, E. W.; Belohradsky, M.; Raymo, F. M.; Stoddart, J. F.; Kuekes, P. J.; Williams, R. S.; Heath, J. R. Science 1999, 285, 391. (c) Feng, M.; Guo, X. F.; Lin, X.; He, X. B.; Ji, W.; Du, S. X.; Zhang, D. Q.; Zhu, D. B.; Gao, H. J. J. Am. Chem. Soc. 2005, 27, 15338. (d) Balzani, V.; Credi, A.; Raymo, F. M.; Stoddart, J. F. Angew. Chem., Int. Ed. 2000, 39, 3348. (e) Zheng, B.; Zhang, M.; Dong, S. Y.; Liu, J.; Huang, F. H. Org. Lett. 2012, 14, 306. (f) Yamada, Y.; Mihara, N.; Shibano, S.; Sugimoto, K.; Tanaka, K. J. Am. Chem. Soc. 2013, 135, 11505. (g) Shen, J. F.; Yu, X. T.; Ye, Y. Y.; Chen, R. E.; Jiang, H. J.; Zhou, Q. Z. Chin. J. Org. Chem. 2012, 32, 2265 (in Chinese). (沈健芬, 于雪涛, 叶余原, 陈仁尔, 蒋华江, 周其忠, 有机化学, 2012, 32, 2265.) (h) Xue, W.; Li, Z. Y.; Liu, G. X.; Chen, X. Q.; Li, T. T.; Liu, S. H.; Yin, J. Org. Biomol. Chem. 2014, 12(27), 4862.
[2] (a) Ballardini, R.; Balzani, V.; Credi, A.; Gandolfi, M. T.; Venturi, M. Acc. Chem. Res. 2001, 34, 445. (b) Li, Z. T. Chin. J. Org. Chem. 2000, 20, 655 (in Chinese). (黎占亭, 有机化学, 2000, 20, 655.) (c) Li, H.; Xu, X. C.; Chen, J. W.; Yang, C. L.; Qin, J. G. Chin. J. Org. Chem. 2008, 28, 2057 (in Chinese). (李昊, 许曦晨, 陈嘉伟, 杨楚罗, 秦金贵, 有机化学, 2008, 28, 2057.) (d) Liu, P.; Shao, X. G.; Cai, W. S. Prog. Chem. 2013, 25(5), 692 (in Chinese). (刘鹏, 邵学广, 蔡文生, 化学进展, 2013, 25(5), 692.)
[3] (a) Ji, F. Y.; Zhu, L.-L. Chin. J. Org. Chem. 2011, 31, 973 (in Chinese). (纪奉元, 朱亮亮, 有机化学, 2011, 31, 973.) (b) Zhai, C. X.; Huang, F. H. Sci. China Chem. 2009, 39, 315 (in Chinese). (翟春熙, 黄飞鹤, 中国科学: 化学, 2009, 39, 315.)
[4] Chambron, J. C.; Heitz, V.; Sauvage, J. P. J. Chem. Soc., Chem. Commun. 1992, 1131.
[5] Anelli, P. L.; Ashton, P. R.; Ballardini, R.; Balzani, V.; Delgado, M.; Gandolfi, M. T.; Goodnow, T. T., Kaifer, A. E.; Philp, D.; Pietraszkiewicz, M.; Prodi L.; Reddington, M. V.; Slawin, A. M. Z.; Spencer, N.; Stoddart, J. F.; Vicent, C.; Williams, D. J. J. Am. Chem. Soc. 1992, 114, 193.
[6] Ashton, P. R.; Ballardini, R; Balzani, V.; Lohradsky, M.; Gandolfi, M. T.; Philp, D.; Prodi, L.; Raymo, F. M.; Reddington, M. V.; Spencer, N.; Stoddart, J. F.; Venturi, M.; Williams, D. J. J. Am. Chem. Soc. 1996, 118, 4931.
[7] Chiu, C. W.; Lai, C. C.; Chiu, S. H. J. Am. Chem. Soc. 2007, 129, 3500.
[8] (a) Reuter, C.; Wienand, W.; Hübner, G. M.; Seel, C.; Vögtle, F. Chem. Eur. J. 1999, 5, 2692. (b) Seel, C.; Vögtle, F. Chem. Eur. J. 2000, 6, 21.
[9] Hirose, K.; Nishihara, K.; Harada, N.; Nakamura, Y.; Masuda, D.; Araki, M.; Tobe, Y. Org. Lett. 2007, 9, 2969.
[10] Winn, J.; Pinczewska, A.; Goldup, S. M. J. Am. Chem. Soc. 2013, 135, 13318.
[11] Feng, Y. H.; Li, J. N.; Jiang, L. S.; Gao, Z. H.; Huang, W. C.; Jiang, F.; Luo, N. H.; Han, S. J.; Zeng, R. H.; Yang, D. Q. Eur. J. Org. Chem. 2011, 3, 562.
[12] Chen, M.-J.; Zhou, S.-G.; Li, M.; Lei, C.-Y.; Xiao, R,; Jiang, L.-S. Chem. Res. Chin. Univ. 2013, 29, 1094.
[13] (a) Loeb, S. J.; Wisner, J. A. Angew. Chem., Int. Ed. 1998, 37, 2838. (b) Ashton, P. R.; Ballardini, R.; Balzani, V.; Credi, A.; Dress, K. R.; Ishow, E.; Kleverlaan, C. J.; Kocian, O.; Preece, J. A.; Spencer, N.; Stoddart, J. F.; Venturi, M.; Wenger, S. Chem. Eur. J. 2000, 6, 3558.
[14] Jiang, L. S.; Okano, J.; Orita, A.; Otera, J. Angew. Chem., Int. Ed. 2004, 43, 2121.

[1]	Wenjin Ma, Haiping Liu, Tian Lei, Haiping Qiu, Jiayao Yuan, Wenling Li. Stereoselective Synthesis of Stilbene C-Glucosides [J]. Chinese Journal of Organic Chemistry, 2024, 44(9): 2943-2949.
[2]	Tao Zeng, Shusheng Zhang, Jianguo Fu, Chenguo Feng. Asymmetric Synthesis of Hamaudol and sec-O-Glucosylhamaudol in Saposhnikovia divaricata (Turcz.) Schischk [J]. Chinese Journal of Organic Chemistry, 2024, 44(9): 2862-2868.
[3]	Ying Fan, Danfeng Huang, Hu Ma, Zuyu Bai, Ke-Hu Wang, Junjiao Wang, Yulai Hu. Synthesis of Difluoromethyl Substituted 1,2,4-Triazoline Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(9): 2820-2831.
[4]	Jinbin Gao, Yingqi Lu, Hui Zhang, Lizhu Gao, Xingquan Xiong. Application of Biobased Catalysts in Chemical Conversion of CO₂ [J]. Chinese Journal of Organic Chemistry, 2024, 44(9): 2732-2741.
[5]	Wei Peng, Rong Cheng, Hao Liu, Dongmei Liu, Xianbin Su. Highly Efficient Continuous Flow Liquid-Phase Peptide Synthesis Using a Soluble Hydrophobic Tag [J]. Chinese Journal of Organic Chemistry, 2024, 44(9): 2876-2888.
[6]	Qingbao Gong, Xiang Lü, Changjiang Yu, Wanwan Li, Quansheng Zhao, Lijuan Jiao, Erhong Hao. Aggregation-Induced Emission (AIE) Active Fluoroboronated Pyridylhydrazinyl Aldehyde Hydrozone Dyes: Synthesis, Crystal Structure and Optical Properties [J]. Chinese Journal of Organic Chemistry, 2024, 44(8): 2545-2553.
[7]	Yujie Yang, Wei Cao, Jikai Yu, Zhixia Zhang, Li Xu, Hua Wang. Synthesis of Donor-Acceptor (D-A) Typed Phenylcyclooctatetrathiophenes and Their Performances on Aggregation Induced Emission and High Pressure Luminescence [J]. Chinese Journal of Organic Chemistry, 2024, 44(8): 2495-2503.
[8]	Shuai Yang, Jie Wu, Liangliang Wang. Asymmetric Total Synthesis towards the Simplified Analogs of Antibiotic Elansolid A [J]. Chinese Journal of Organic Chemistry, 2024, 44(7): 2350-2362.
[9]	Liusong Lan, Qian Yang, Yongyi Li, Shujun Fang, Yuxuan Huang, Juncheng Su, Chengxue Pan, Guifa Su. Synthesis and Anti-neuroinflammatory Activities of 25-Hydroxycholesterol and Its Analogues [J]. Chinese Journal of Organic Chemistry, 2024, 44(7): 2305-2314.
[10]	Lingdong Li, Weilun Zhang, Pengfei Liu, Zijie Zhou, Hao Zhou, Zhongtian Du. Synthesis of Gemini-Quaternary Ammonium N-Chloramine Biocides for Antibacterial Applications [J]. Chinese Journal of Organic Chemistry, 2024, 44(6): 2041-2048.
[11]	Jianling Hu, Chao Zhang, Wenda Zhu, Yepu He, Shuling Peng, Zhenqiang Chen, Mingyue Li, Zhiju Liu, Heru Chen. Design, Synthesis, and Preliminary Anti-tumor Activity Studies of Novel 1,2-Disubstituted Hydrazines [J]. Chinese Journal of Organic Chemistry, 2024, 44(6): 1870-1883.
[12]	Liqing Qin, Guishan Lin, Wengui Duan, Yucheng Cui, Maofang Yang, Fangyao Li, Dianpeng Li. Synthesis, Antiproliferative Activity, 3D-QSAR and Molecular Docking Study of Novel Longifolene-Derived Tetraline Fused N-Acyl-pyrazole Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(6): 1967-1977.
[13]	Leilei Liang, Jiacan Yao, Fan Ding, Chang Xu, Dandan Liu. Research Progress on the Synthetic Methods of Pancratistatin [J]. Chinese Journal of Organic Chemistry, 2024, 44(6): 1793-1810.
[14]	Yiping Sun, Demao Chen, Ling He, Zuli Wang. Na₂S₂O₈ Mediated C—H Amination of Imidazo[1,2-α]pyridines with Heteroaromatic Amines under Metal-Free Conditions [J]. Chinese Journal of Organic Chemistry, 2024, 44(5): 1667-1674.
[15]	Jiyong Liu, Minghui Wu, Juncheng Xiang, Huailin Pang, Bin Li, Liang Lü. Synthesis, Insecticidal Activities, and Structure-Activity Relationship Studies of Novel Diamide Compounds Containing (Halogenated) Alkoxy Group [J]. Chinese Journal of Organic Chemistry, 2024, 44(5): 1584-1591.

一锅法合成基于丁二炔-苯环冠醚的[2]轮烷

One-Pot Synthesis of A New [2]rotaxane Based on the Phenylene-Diacetylene Crown Ether

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments