三蝶烯衍生大三环主体与π-延展双吡啶盐之间络合性质的研究

doi:10.6023/A15070447

摘要/Abstract

描述了三蝶烯衍生大三环主体与π-延展双吡啶盐在溶液中与固态下的络合性质, 表明由于客体中两个吡啶盐之间连接单元的不同及端基官能团的不同, 大三环主体与π-延展双吡啶盐能够形成1:1或1:2络合物, 也可以在固态下形成梯状聚准[3]轮烷型超分子组装体. 络合物的形成得到了核磁共振氢谱、质谱以及X衍射单晶结构证明.

关键词: 三蝶烯, 大三环主体, 络合作用, π-延展双吡啶盐

Development of novel macrocyclic hosts with the capability of binding selected substrates in specific complexation modes is always a very important and attractive topic in host-guest chemistry. Recently, we reported a novel macrotricyclic polyether containing two triptycene skeletons with rigid structure and two dibenzo-30-crown-10 moieties, which could show wide complexation abilities toward different kinds of guests. It was found that depending on the guests with different terminal functional groups and structures, the macrotricyclic polyether could form 1:1 or 1:2 complexes with the guests in different complexation modes in solution and also in the solid state. Moreover, the conformation of the macrocycle could easily be adjusted by the different encapsulated guests, which was to some extent similar to substrate induced fit of enzymes. It was also known that viologens with reversible single electron-accepting ability were usually used for the basic study of electrochemical and photoelectrochemical processes. They have also been widely utilized as electron deficient guests for host-guest chemistry. Compared with the viologens, π-extended viologens with conjugated structures have much more rich redox behaviors, and they could be used for photolithography, a source of electric oscillations, molecular electronic devices, and also as agents for charge transport across vesicles. However, the applications of π-extended viologens as guests in host-guest chemistry are still very limited. In this paper, complexation between the triptycene-derived macrotricyclic host and π-extended viologens in both solution and solid state was investigated in detail. It was found that depending on the guests with different linker-species and terminal functional groups, the macrotricyclic host could form 1:1 or 1:2 complexes with the guests in solution. Besides the 1:1 or 1:2 complexes, the macrotricyclic host could also form supramolecular poly[3]pseudorotaxane-type complexes with the guests in different complexation modes in the solid state. Formation of the complexes was proved by the ¹H NMR, ESI-MS spectra, and X-ray crystal structures.

Key words: triptycene, macrotricyclic host, complexation, π-extended viologen

引用此文

韩莹, 孟征, 陈传峰. 三蝶烯衍生大三环主体与π-延展双吡啶盐之间络合性质的研究[J]. 化学学报, 2015, 73(11): 1147-1152.

Han Ying, Meng Zheng, Chen Chuanfeng. Complexation of Triptycene-Derived Macrotricyclic Host with π-Extended Viologens[J]. Acta Chim. Sinica, 2015, 73(11): 1147-1152.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

参考文献

[1]
(a) Lehn, J.-M. Supramolecular Chemistry, VCH Publishers, New York, 1995.
(b) Macrocyclic Chemistry: Current Trends and Future Perspectives, Ed.: Gloe, K., Springer, The Netherlands, 2005.
(c) Chen, C.-F.; Ma, Y.-X. Iptycene Chemistry: From Synthesis to Applications, Springer-Verlag, Berlin Heidelberg, 2013.
(d) Zhang, Z. B.; Luo, Y.; Chen, J. Z.; Dong, S. Y.; Yu, Y. H.; Ma, Z.; Huang, F. H. Angew. Chem., Int. Ed. 2011, 50, 1397.
(e) Shi, Z. M.; Song, Y.; Lu, F.; Zhou, T. Y.; Zhao, X.; Zhang, W. K.; Li, Z. T. Acta Chim. Sinica 2013, 71, 51. (施朱明, 宋宇, 陆方, 周天佑, 赵新, 张文科, 黎占亭, 化学学报, 2013, 71, 51.)
(f) Han, C.; Xu, Z.; Diao, C. H.; Chen, X.; Liu, J.; Guo, M. J.; Fan, Z. Acta Chim. Sinica 2013, 71, 439. (韩聪, 徐喆, 刁春华, 陈鑫, 刘靖, 郭敏杰, 樊志, 化学学报, 2013, 71, 439.)
(g) Zhou, L.; Xu, L. J.; Gong, H. Y. Acta Chim. Sinica 2014, 72, 447. (周丽, 徐立进, 龚汉元, 化学学报, 2014, 72, 447.)
(h) Yi, J. M.; Xiao, X.; Zhang, Y. Q.; Xue, S. F.; Tao, Z.; Zhang, J. X. Acta Chim. Sinica 2014, 72, 949. (易君明, 肖欣, 张云黔, 薛赛凤, 陶朱, 张建新, 化学学报, 2014, 72, 949.)
(i) Yue, S. Y.; Zhou, Y. J.; Yao, Y.; Xue, M. Acta Chim. Sinica 2014, 72, 1053. (岳诗雨, 周玉娟, 姚勇, 薛敏, 化学学报, 2014, 72, 1053.)
(j) Wang, Z.; Zhou, H. J.; Hu, J. Y.; You, J. S.; Gao, G. Acta Chim. Sinica 2013, 71, 1257. (王志, 周红军, 胡俊毅, 游劲松, 高戈, 化学学报, 2013, 71, 1257.)
[2]
(a) Zeng, F.; Han, Y.; Yan, Z.-C.; Liu, C.-Y.; Chen, C.-F. Polymer 2013, 54, 6929.
(b) Zeng, F.; Shen, Y.; Chen, C.-F. Soft Matter 2013, 9, 4875.
(c) Han, Y.; Gu, Y.-K.; Xiang, J.-F.; Chen, C.-F. Chem. Commun. 2012, 48, 11076.
[3]
(a) Sauvage, J. P.; Dietrich-Buchecker, C. Molecular Catenanes, Rotaxanes and Knots, VCH Publishers, Weinheim, 1999.
(b) Badji?, J. D.; Nelson, A.; Cantrill, S. J.; Turnbull, W. B.; Stoddart, J. F. Acc. Chem. Res. 2005, 38, 723.
(c) Chong, J. H.; MacLachlan, M. J. Chem. Soc. Rev. 2009, 38, 3301.
(d) Chen, C.-F. Chem. Commun. 2011, 47, 1674.
(e) Yang, J. S.; Yan, J. L. Chem. Commun. 2008, 1501.
(f) Han, Y.; Meng, Z.; Ma, Y.-X.; Chen, C.-F. Acc. Chem. Res. 2014, 47, 2026.
[4]
(a) Ballardini, R.; Balzani, V.; Credi, A.; Gandolfi, M. T.; Venturi, M. Acc. Chem. Res. 2001, 34, 445.
(b) Meng, Z.; Xiang, J.-F.; Chen, C.-F. Chem. Sci. 2014, 5, 1520.
[5]
(a) Blanco, V.; Leigh, D. A.; Marcos, V.; Morales-Serna, J. A.; Nussbaumer, A. L. J. Am. Chem. Soc. 2014, 136, 4905.
(b) Suzaki, Y. J.; Shimada, K.; Chihara, E.; Saito, T.; Tsuchido, Y.; Osakada, K. Org. Lett. 2011, 13, 3774.
[6]
(a) Isaacs, L. Chem. Commun. 2009, 619.
(b) Loeb, S. J. Chem. Soc. Rev. 2007, 36, 226.
[7]
(a) Zong, Q.-S.; Chen, C.-F. Org. Lett. 2006, 8, 211.
(b) Zhao, J.-M.; Zong, Q.-S.; Chen, C.-F. J. Org. Chem. 2010, 75, 5092.
(c) Han, Y.; Lu, H.-Y.; Zong, Q.-S.; Guo, J.-B.; Chen, C.-F. J. Org. Chem. 2012, 77, 2422.
(d) Han, T.; Chen, C.-F. J. Org. Chem. 2007, 72, 7287.
(e) Han, T.; Chen, C.-F. Org. Lett. 2006, 8, 1069.
(f) Peng, X.-X.; Lu, H.-Y.; Han, T.; Chen, C.-F. Org. Lett. 2007, 9, 895.
(g) Jiang, Y.; Cao, Y.; Zhao, J.-M.; Xiang, J.-F.; Chen, C.-F. J. Org. Chem. 2010, 75, 1767.
(h) Guan, Y. F.; Ni, M. F.; Hu, X. Y.; Xiao, T. X.; Xiong, S. H.; Lin, C.; Wang, L. Y. Chem. Commun. 2012, 48, 8529.
(i) Li, S. L.; Xiao, T. X.; Hu, B. J.; Zhang, Y. J.; Zhao, F.; Ji, Y.; Yu, Y. H.; Lin, C.; Wang, L. Y. Chem. Commun. 2011, 47, 10755.
(j) Zhang, Z. J.; Zhang, H. Y.; Chen, L.; Liu, Y. J. Org. Chem. 2011, 76, 8270.
(k) Han, Y.; Guo, J.-B.; Cao, J.; Chen, C.-F. Chin. J. Chem. 2013, 31, 607.
(l) Wang, F.; Han, C.; He, C.; Zhou, Q.; Zhang, J.; Wang, C.; Li, N.; Huang, F. J. Am. Chem. Soc. 2008, 130, 11254.
(m) Zheng, B.; Wang, F.; Zhang, J.; Ding, X.; Dong, S.; Liu, M.; Zheng, B.; Li, S.; Zhu, K.; Wu, L.; Yu, Y.; Gibson, H. W.; Huang, F. Angew. Chem., Int. Ed. 2010, 49, 1090.
[8]
(a) Porter III, W. W.; Vaid, T. P.; Rheingold, A. L. J. Am. Chem. Soc. 2005, 127, 16559.
(b) Hromadová, M.; Kolivoška, V.; Sokolová, R.; Gál, M.; Pospíšil, L.; Valášek, M. Langmuir 2010, 26, 17232.
(c) Nakagawa, M.; Oh, S. K.; Ichimura, K. Adv. Mater. 2000, 12, 403.
[9]
(a) Su, Y.-S.; Chen, C.-F. Org. Lett. 2010, 12, 1888.
(b) Stancl, M.; Hodan, M.; Sindelar, V. Org. Lett. 2009, 11, 4184.
(c) Yan, X. Z.; Zhang, M. M.; Wei, P. F.; Zheng, B.; Chi, X. D.; Ji, X. F.; Huang, F. H. Chem. Commun. 2011, 47, 9840.
(d) Choi, S. W.; Ritter, H. Macromol. Rapid Commun. 2007, 28, 101.
(e) Chi, X. D.; Xue, M. RSC Adv. 2014, 4, 365.
[10]
(a) Han, Y.; Cao, J.; Li, P.-F.; Zong, Q.-S.; Zhao, J.-M.; Guo, J.-B.; Xiang, J.-F.; Chen, C.-F. J. Org. Chem. 2013, 78, 3235.
(b) Guo, J.-B.; Han, Y.; Cao, J.; Chen, C.-F. Org. Lett. 2011, 13, 5688.
(c) Han, Y.; Jiang, Y.; Chen, C.-F. Chin. Chem. Lett. 2013, 24, 475.
[11] Han, Y.; Gu, Y.-K.; Guo, J.-B.; Chen, C.-F. Eur. J. Org. Chem. 2015, 1257.
[12]
(a) Connors, K. A. Binding Constants, John Wiley and Sons, New York, 1987.
(b) Huang, F.; Jones, J. W.; Slebodnick, C.; Gibson, H. W. J. Am. Chem. Soc. 2003, 125, 14458.
[13] See the Supporting Information.
[14] Zhao, J.-M.; Zong, Q.-S.; Chen, C.-F. J. Org. Chem. 2010, 75, 5092.
[15] Schmauch, G.; Knoch, F.; Kisch, H. Chem. Ber. 1994, 127, 287.
[16] Yan, X. Z.; Wei, P. F.; Zhang, M. M.; Chi, X. D.; Liu, J. Y.; Huang, F. H. Org. Lett. 2011, 13, 6370.
[17] Nanasawa, M.; Miwa, M.; Hirai, M.; Kuwabara, T. J. Org. Chem. 2000, 65, 593.
[18] Barnes, J. C.; Juricek, M.; Strutt, N. L.; Frasconi, M.; Sampath, S.; Giesener, M. A.; McGrier, P. L.; Bruns, C. J.; Stern, C. L.; Sarjeant, A. A.; Stoddart, J. F. J. Am. Chem. Soc. 2013, 135, 183.