Progress on Heteroaromatic Molecular Tweezers Involving Multiple Hydrogen-bonding Sites

Abstract

Cite this article

MU Qi-Ming, PENG You, ZHAO Zhi-Gang, CHEN Shu-Hua. Progress on Heteroaromatic Molecular Tweezers Involving Multiple Hydrogen-bonding Sites[J]. Chinese Journal of Organic Chemistry, 2004, 24(9): 1018-1028.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

1 Schmidtchen, F. P.; Berger, M. Chem. Rev. 1997, 97, 1609.
2 Beer, P. D.; Gale, P. A. Angew. Chem., Int. Ed. 2001, 40, 486.
3 Webb, T. H.; Wilcox, C. S. Chem. Soc. Rev. 1993,383.
4 Zhang, X. X.; Bradshaw, J. S.; Izatt, R. M. Chem. Rev. 1997, 97, 3313.
5 Fizmaurice, R. J.; Kyne, G. M.; Douheret, D.; Kilburn, J. D. J. Chem. Soc., Perkin Trans. 1 2002, 841.
6 Lavigne, J. J.; Ansly, E. V. Angew. Chem., Int. Ed. 2001, 40, 3118.
7 Mu, Q.-M.; Xue, C.-H.; Chen, S.-H. Chem.Res. Appl. 2001, 13, 473 (in Chinese).
(牟其明, 薛翠花, 陈淑华, 化学研究与应用, 2001, 13, 473.)
8 Lehn, J. M. Angew. Chem., Int. Ed. Engl. 1988, 27, 89.
9 Robertson, A.; Shinkai, S. Coord. Chem. Rev. 2000, 205, 157.
10 Gunnlaugsson, T.; Davis, A. P.; O'Brien, J. E.; Glynn, M. Org. Lett. 2002, 4, 2449.
11 Liao, J.-H.; Chen, C.-T.; Fang, J.-M. Org. Lett. 2002, 4, 561.
12 Allen, W. E.; Causey, C. P. J. Org. Chem. 2002, 67, 5963.
13 Kondo, S.; Sakuno, Y.; Yokoyama, T.; Yano, Y. Chem. Lett. 2001, 830.
14 Prohens, R.; Tomàs, S.; Morey, J.; Deyà, P. M.; Ballester, P.; Costa,A. Tetrahedron Lett. 1998, 39, 1063.
15 Tobe, Y.; Sasaki, S.; Mizuno, M.; Hirose, K.; Naemura, K. J. Org. Chem. 1998, 63, 7481.
16 Lee, D. H.; Lee, H. Y.; Lee, K. H.; Hong, J. I. Chem. Commun. 2001, 1188.
17 (a) Fan, E.; Van Arman, S. A.; Kincaid, S.; Hamilton, A. D. J. Am. Chem. Soc. 1993, 115, 369.
(b) Nishizawa, S.; Buhlmann, P.; Zwao, M.; Umezawa, Y. Tetrahedron Lett. 1995, 36, 6483.
18 Büohmann, P.; Nishizawa, S.; Xiao, K. P.; Umezawa, Y. Tetrahedron1997, 53, 1647.
19 Xiao, K. P.; Büchmann, P.; Nishizawa, S.; Amemiya, S.; Umezawa, Y. Anal. Chem. 1997, 69, 1038.
20 de la Torre, M.; Campos, E. G.; González, S.; Morán, J. R.; Caballero, M. Tetrahedron 2001, 57, 3945.
21 Kelly, T. R.; Kim, M. H. J. Am. Chem. Soc. 1994, 116, 7072.
22 Jeong, K.; Park, J. W.; Cho, Y. L. Tetrahedron Lett. 1996, 37, 2795.
23 Hamann, B. C.; Branda, N. R.; Rebek Jr, J. Tetrahedron Lett. 1993, 34, 6837.
24 Kyne, G. M.; Light, M. E.; Hursthouse, M. B.; de Mendoza, J.; Kilburn,J. D. J. Chem. Soc., Perkin Trans. 1 2001, 1258.
25 Benito, J. M.; Gómez-García, M.; Jiménez Blanco, J. L.; Mellet, C.O.; García Femández, J. M. J. Org. Chem. 2001, 66,1366.
26 Mu, Q.-M.; Xue, C.-H.; Chen, S.-H. Progress in Macrocyclic and Supramolecular Chemistry, Xian, 2002, p. 226 (in Chinese).
(牟其明, 薛翠花, 陈淑华. 大环化学和超分子化学研究进展论文选集, 西安, 2002, p. 226.)
27 Mu, Q.-M. Ph.D. Dissertation, Sichuan University, Chengdu, 2003 (in Chinese).
(牟其明, 博士论文, 四川大学, 2003.)
28 Goswami, S.; Hamilton, A. D.; Van Engen, D. J. Am. Chem. Soc. 1989, 111, 3425.
29 Goswami, S.; Mukherjee, R. Tetrahedron Lett. 1997, 38, 1619.
30 Jr Adrian, J. C.; Willox, C. S. J. Am. Chem. Soc. 1989,111, 8055.
31 Kelly, T. R.; Maguire, M. P. J. Am. Chem. Soc. 1987, 109, 6549.
32 Bell, T. W.; Lin, J. J. J. Am. Chem. Soc. 1988, 110, 3673.
33 Bell, T. W.; Hext, N. M.; Khasanov, A. B. Pure Appl. Chem. 1998, 70, 2371.
34 Goswami, S.; Mahapatra, A. K.; Mukherjee, R. J. Chem. Soc., Perkin Trans. 1 2001, 2717.
35 Martín, M.; Raposo, C.; Oliva, A. I.; Simón, L.; Caballlero, C.; Morán, J. Chem. Lett. 2000, 718.
36 Bell, T. W.; Hou, Z.; Luo, Y.; Drew, M. G. B.; Chapoteau, E.; Czech, B.P.; Kumar, A. Science (Washington, D. C.) 1995, 269,671.
37 Beckles, D. L.; Maioriellc, J.; Santora, V. J.; Bell, T. W. Tetrahedron 1995, 51, 363.
38 (a) Hamilton, A. D. J. Am. Chem. Soc. 1990, 112, 7391.
(b) Vicent, C.; Hirst, S. C.; Garcia-Tellado, F.; Hamilton, A. D.J. Am. Chem. Soc. 1991, 113, 5466.
39 Goswami, S.; Ghosh, K.; Halder, M. Tetrahedron Lett. 1999, 40, 1735.
40 Bilz, A.; Stork, T.; Helmchen, G. Tetrahedron: Asymmetry 1997, 8, 3999.
41 Goswami, S.; Ghosh, K.; Dasgupta, S. Tetrahedron Lett. 1996, 52, 12223.
42 Fan, E. K.; Vicent, C.; Hamilton, A. D. New J. Chem. 1997, 21, 81.
43 Ray, J. K.; Gupta, S.; Pan, D.; Kar, G. K. Tetrahedron 2001, 57, 7213.
44 Goswami, S.; Ghosh, K.; Mukherjee, R. Tetrahedron 2001,57, 4987.
45 Mussons, L.; Raposo, C.; dela Torre, F.; Moran, J. R.; Caballero, C. Tetrahedron 1999, 55, 4077.
46 Goswami, S.; Ghosh, K.; Dasgupta, S. J. Org. Chem. 2000,65, 1907.
47 Garcia-Tellado, F.; Albert, J.; Hamilton, A. D. J. Chem. Soc., Chem.Commun. 1991, 1761.
48 Hernández, J. V.; Almaraz, M.; Raposo, C.; Martín, M.; Lithgow, A.; Crego, M.; Caballero, C.; Morán, J. R. Tetrahedron Lett. 1998, 39, 7401.
49 Martín, M.; Raposo, C.; Almaraz, M.; Crego, M.; Caballero, C.; Grande,M.; Morán, J. R. Angew. Chem., Int. Ed. Engl. 1996, 35, 2386.
50 Tecilla, P.; Chang, S.-K.; Hamilton, A. D. J. Am. Chem. Soc. 1990, 112, 9586.
51 Tecilla, P.; Jubian, V.; Hamilton, A. D. Tetrahedron 1995, 51, 435.
52 Aoki, I.; Harada, T.; Sakaki, T.; Kawahara, Y.; Shinkai, S. J. Chem.Soc., Chem. Commun. 1992, 1341.
53 Zhao, Z.-M.; Mu, Q.-M.; Hu, R.; Yang, Z.-X.; Chen, S.-H. J. Sichuan. Univ. (Nat. Sci. Ed.) 2001, 38, 402 (in Chinese).
(赵志明, 牟其明, 胡蓉, 杨祖幸, 陈淑华, 四川大学学报(自然科学版), 2001, 38, 402.)
54 Mu, Q.-M.; Zhao, Z.-M.; Chen, S.-H. Acta Chim. Sinica 2002, 60, 1841 (in Chinese).
(牟其明, 赵志明, 陈淑华, 化学学报, 2002, 60, 1841.)
55 Raposo, C.; Almaraz, M.; Pérez, N.; Martín, M.; Weinrich, V.; Grande,M.; Caballero, M.; Morán, J. R. Tetrahedron Lett. 1996, 37, 1485.
56 Yang, W.; He, H.; Drueckhammer, D. G. Angew. Chem. Int. Ed. 2001, 40, 1714.
57 (a) Tomoyuki, O.; Yayoi, Y.; Yasushi, Y. Bull. Chem. Soc. Jpn. 2001, 74, 2181.
(b) Yamabe, T.; Hori, K.; Akagi, K.; Fukui, K. Tetrahedron 1979, 35, 1065.
(c) Zheng, Q. T.; Chen, C. F.; Huang, Z. T. Tetrahedron 1997, 53, 10345.
(d) Liu, Y.; Qi, A.-D.; Han, B.-H.; Li, Y.-M.; Chang, Y.-M.; Cheng, R.-T. Chin. Sci. Bull. 1997, 42, 1516 (in Chinese).
(刘育, 戚爱棣, 韩宝航, 李玉梅, 张毅民, 陈荣梯, 科学通报, 1997, 42, 1516.)
58 (a) You, C.-C.; Liu, Y. Chem. J. Chin. Univ. 2000, 21, 249.
(尤长城, 刘育, 高等学校化学学报, 2000, 21, 249.)
(b) Liu, Y.; You, C.-C.; He, S.; Chen, G.-S.; Zhao, Y.-L. J.Chem. Soc., Perkin Trans. 2 2002, 463.
59 (a) Bukownik, R. R.; Wilicox, C. S. J. Am. Chem. Soc. 1988, 110, 6204.
(b) Arrecke, R.; Bohmer, V.; Cacciapaglia, R.; Cort, A. D.; Mandolini, L. Tetrahedron 1997, 53, 4901.
(c) Davidson, R. B.; Bradshaw, J. S.; Jones, B. A.; Dalley, N. K.;Christensen, J. J.; Zzatt, R. M. J. Org. Chem. 1992, 57, 275.
(d) Zhu, C. Y.; Bradshaw, J. S.; Vscavson, J. L.; Izatt, R. R. J. Inclusion Phenom. Mol. Recognit. Chem. 1992, 12, 275.
60 Liu, Y.; Zhang, Y. M.; Sun, S. X.; Li, Y. M.; Chen, R. T. J. Chem. Soc., Perkin Trans. 2 1997, 1606.
61 (a) Sawada, M.; Takai, Y.; Yamada, H.; Nishida, J.; Kaneda, T.; Arakawa, R.; Okamoto, M.; Hirose, K.; Tanaka, T.; Naemura, K. J. Chem. Soc., Perkin Trans. 2 1998, 701.
(b) Krishna, P.; Prabhakar, S.; Manoharan, M.; Jemmis, E. D.; Vairamani, M. Chem. Commun. 1999, 1215.
62 Boerrigter, H.; Grare, L.; Nissink, J. W. M.; Chrisstoffels, L. A. J.;van der Maas, J.; Verboom, W.; de Jong, F.; Reinhoudt, D. N. J. Org. Chem.1998, 63, 4174.
63 (a) Lee, H. J.; Yoon, I. J.; Yoo, C. L.; Pyun, H-J.; Cha, G. S.; Nam,H. Anal. Chem. 2000, 72, 4694.
(b) Seiichi, N.; Tomoyuki, Y.; Ryo, K.; Takeshi, S.; Norio, T. Bull. Chem. Soc. Jpn. 2001, 74, 2343.
64 (a) Kakeda, Y.; Goto, H. Bull. Chem. Soc. Jpn. 1979, 52, 1920.
(b) Potluri, V. K.; Maitra, U. J. Org. Chem. 2000, 65, 7764.
(c) Ayling, A. J.; Broderick, S.; Clare, J. P.; Davis, A. P.; Pérez-Payán, M. N.; Lahtinen, M.; Nissinen, M. J.; Rissanen, K. Chem. Eur. J. 2002, 8, 2197.
65 (a) Inoue, Y.; Hakushi, T.; Liu, Y.; Tong, L. H.; Bao, J. S.; Jin, D. S. J. Am. Chem. Soc. 1993, 115, 475.
(b) Eatough, D. J.; Christensen, J. J.; Izatt, R. M. Thermochim.Acta. 1972, 3, 219.
66 Chen, G.-Z.; Huang, X.-Z.; Liu, W.-Y.; Zheng, Z.-Z.; Wang, Z.-B.UV-vis Spectroscopy, Atomic Energy Publishing House, Beijin, 1983 (in Chinese).
(陈国珍, 黄显智, 刘文远, 郑朱梓, 王尊本, 紫外-可见分光光度法, 原子能出版社, 北京, 1983.)
67 Hao, A.-Y.; Tong, L.-H.; Gao, X.-M.; Zhang, F.-H. Acta Phys.-Chim. 1995, 11(3), 202 (in Chinese).
(郝爱有, 童林荟, 高兴明, 张复升, 物理化学学报, 1985, 11(3), 202.)
68 Zhou, J.; He, J.-W.; Zhao, J.; Shi, H.-M. Chem. J. Chin. Univ. 1999, 20(10), 204 (in Chinese).
(周杰, 何俊文, 赵洁, 史慧明, 高等学报化学学报, 1999, 20(10), 204.)
69 Benesi, H. A.; Hliderbrand, J. H. J. Am. Chem. Soc. 1949, 71, 2703.
70 Cramer, F.; Seanger, W.; Spatz, H. C. J. Am. Chem. Soc. 1967, 87, 14.
71 Liu, Y.; Yamamota, K.; Wada, T.; Everitt, S.; Gao, X.-M.; Hou, Z.-J.;Tong, L.-H.; Jiang, S.-K.; Wu, H.-M. J. Chem. Soc., Perkin Trans. 2 1998, 1807.
72 Lu, G.-Y.; Hu, H.-W. Sci. China., Ser. B 1996, 26(4), 298 (in Chinese).
(陆国元, 胡宏纹, 中国科学(B辑), 1996, 26(4), 289.)

[1]	Zimeng Shao, Yuanhui Wang, Haiying Wang, Peipei Cui, Xuguang Liu. Recent Advance in the Synthesis of Ullazine and Its Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3679-3694.
[2]	Qiang Yan, Rong Fan, Binbin Liu, Shuaisong Su, Bo Wang, Tuanli Yao, Jiajing Tan. Recent Progress in Aryne Participated Dearomatization Reactions [J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 455-470.
[3]	Huang Guobao, Chen Zhilin, Wei Xiansheng, Chen Yu, Li Xiuying, Zhong Hui, Tan Mingxiong. Recent Progress on the Construction and Function of Macrocyclic Compounds Containing Hydrogen Bond Donors [J]. Chinese Journal of Organic Chemistry, 2020, 40(3): 614-624.
[4]	Wang Jiao, Yao Hong, Zhou Qi, Kan Xiaotong, Fan Yanqing, Guan Xiaowen, Zhang Youming, Lin Qi, Wei Taibao. Molecule-Responsive Supramolecular Hydrogel Constructed from Pillar[5]arene Based on Host-Guest System [J]. Chinese Journal of Organic Chemistry, 2020, 40(1): 175-180.
[5]	Li, Sicong, Ji, Shaocong, Zhao, Liang, Liao, Xiaoyu, Liu, Chuanfeng, Tang, Haodong, Shu, Zhengning, Yang, Peng, Pei, Yuehu. Syntheses and Property Evaluation of N-Salicylaldehyde Hydrazone Modified 11-Azaartemisinins and Their Derivatives [J]. Chinese Journal of Organic Chemistry, 2019, 39(10): 2860-2866.
[6]	Liu Chuan-Zhi, Wang Hui, Zhang Dan-Wei, Zhao Xin, Li Zhan-Ting. Study on Halogen Bonding of Organofluorine Compounds in China [J]. Chin. J. Org. Chem., 2019, 39(1): 28-37.
[7]	Sun Guangjun, Nie Chengbin, Zhao Xin, Li Zhanting. Intramolecular C-H…O Hydrogen Bonding-Driven 1,2,3-Trazole Foldamers:Assessment of Intermolecular C-H…X^- (X=Cl, Br, I) and C-H…N Hydrogen Bonding [J]. Chin. J. Org. Chem., 2017, 37(7): 1757-1763.
[8]	Xiao Liwei, Ren Ping, Jing Xuemin, Ren Lilei, Li Zheng, Dai Fucai. Application in Molecular Recognition of 1,2,3-Trizole Derivatives [J]. Chin. J. Org. Chem., 2017, 37(12): 3085-3095.
[9]	Li Wenting, Qu Wenjuan, Zhang Haili, Li Xiang, Lin Qi, Yao Hong, Zhang Youming, Wei Taibao. Development on Application of Phenazine Derivatives in Molecular Recognition and Self-assembly [J]. Chin. J. Org. Chem., 2017, 37(10): 2619-2639.
[10]	Liu Guijun, Shi Hao. Progress in Chiral Recognition Based on Molecular Tweezers [J]. Chin. J. Org. Chem., 2016, 36(11): 2583-2601.
[11]	Peng Long, Liu Huijun, Hu Cheng, Sun Yunkai, Long Wei. Terephthaloyl Chloride Bridged Bis(β-cyclodextrin) and Their Synergetic Bonding Behaviors with Dyes [J]. Chin. J. Org. Chem., 2015, 35(6): 1330-1334.
[12]	Weng Guan-Huan, Zhu Bin, Ye Yang, Li Shijun. Acid/Base-Controllable Molecular Machines and Molecular Switches [J]. Chin. J. Org. Chem., 2015, 35(2): 309-324.
[13]	Zhao Zhigang, Wang Xiaohong, Shi Zhichuan, Cheng Yuyu. Synthesis of Molecular Tweezers Derived from Chenodeoxycholic Acid through Click Reaction and Their Recogniton Properties [J]. Chin. J. Org. Chem., 2014, 34(6): 1110-1117.
[14]	Shi Zhichuan, Zhao Zhigang, Li Hui, Tan Jiong. Solvent-Free Synthesis of Novel Schiff Base Type Molecular Tweezers Based on Chenodeoxycholic Acid Promoted by Microwave Irradiation [J]. Chin. J. Org. Chem., 2014, 34(3): 572-577.
[15]	Zhao Bangtun, Zhu Weimin. Progress on Covalently Bonded Calixarene-Tetrathiafulvalene Supramolecules [J]. Chin. J. Org. Chem., 2014, 34(10): 1992-2000.

芳杂环类多重氢键分子钳人工受体研究新进展