溶液酸碱度调控的分子机器与分子开关
收稿日期: 2014-09-09
修回日期: 2014-10-24
网络出版日期: 2014-11-13
基金资助
国家自然科学基金(Nos. 21072039, 91127010)、教育部创新团队(No. IRT1231)、浙江省自然科学基金(No. LZ13B030001)资助项目.
Acid/Base-Controllable Molecular Machines and Molecular Switches
Received date: 2014-09-09
Revised date: 2014-10-24
Online published: 2014-11-13
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21072039, 91127010), the Program for Changjiang Scholars and Innovative Research Team in Chinese University (No. IRT1231), and the Zhejiang Provincial Natural Science Foundation of China (No. LZ13B030001).
人工分子机器按其能量驱动方式可以分为化学驱动、电化学驱动和光驱动三类. 溶液酸碱度调控(pH调控)驱动属于化学驱动的一种, 其基本原理是通过加入酸碱性化合物调节溶液的酸碱度从而改变体系中各种组分的化学性质, 实现分子机器的运动. 利用溶液酸碱度调控已成为人工组装分子机器最常用的能量供应方式之一. 对溶液酸碱度调控的分子机器和分子开关进行了详细综述, 分别总结了基于冠醚和其他大环主体的溶液酸碱度调控分子机器与分子开关的制备及酸碱调控方法, 并展望了它们在信息存储、电子器件及药物传递等领域中的应用.
翁官欢 , 朱彬 , 叶杨 , 李世军 . 溶液酸碱度调控的分子机器与分子开关[J]. 有机化学, 2015 , 35(2) : 309 -324 . DOI: 10.6023/cjoc201409021
There are three kinds of energy-supplied modes to drive artificial molecular machines: chemical stimulation, electrochemical input and light stimulation. The basic principle of acid/base-controlled (or pH-operated) method is to change the chemical properties of components in the system by adjusting pH of the solution via adding acid/base compounds, to realize the movements of components, which belongs to chemical stimulation mode. The acid/base controlled method has been one of the most useful energy-driven modes for artificial molecular machines. This article summarizes the recent studies on acid/base- controllable molecular machines or molecular switches. The synthesis and operation of acid/base-controllable artificial molecular switches and molecular machines based on crown ethers and other macrocyclic hosts are reviewed. They exhibited great potential in the applications for information storage materials, electronic devices, and drug delivery.
[1] (a) Balzani, V.; Credi, A.; Raymo, F. M.; Stoddart, J. F. Angew. Chem. Int. Ed. 2000, 39, 3348.
(b) Kinbara, K.; Aida, T. Chem. Rev. 2005, 105, 1377.
(c) Ballardini, R.; Balzani, V.; Credi, A.; Gandolfi, M. T.; Venturi, M. Acc. Chem. Res. 2001, 34, 445.
(d) Champin, B.; Mobian, P.; Sauvage, J. P. Chem. Soc. Rev. 2007, 36, 358.
(e) Ma, X.; Wang, Q. C.; Tian, H. Process Chem. 2009, 21, 106 (in Chinese). (马骧, 王巧纯, 田禾, 化学进展, 2009, 21, 106.)
(f) Kay, E.R.; Leigh, D.A.; Zerbetto, F. Angew. Chem., Int. Ed. 2007, 46, 72.
(g) Li, H.; Xu, X. C.; Chen, J. W.; Yang, C. L.; Qing, 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.)
(h) Li, S.; Huang, J.; Cook, T. R.; Pollock, B. J.; Kim, H.; Chi, K.-W.; Stang, P. J. J. Am. Chem. Soc. 2013, 135, 2084.
(i) Li, S.; Huang, J.; Zhou, F.; Cook, T. R.; Yan, X.; Ye, Y.; Zhu, B.; Zheng, B.; Stang, P. J. J. Am. Chem. Soc. 2014, 136, 5908.
(j) Zhou, D. X.; Sun, T.; Deng, W. Chin. J. Org. Chem. 2012, 32, 239 (in Chinese). (周冬香, 孙涛, 邓维, 有机化学, 2012, 32, 239.)
(k) Fan, C. H.; Yang, Y. Q.; Zhao, W.; Xiao, Y.; Luo, J.; Liu, X. Y. Acta Chim. Sinica 2013, 71, 934 (in Chinese). (范存华, 杨逸群, 赵伟, 肖宇, 罗静, 刘晓亚, 化学学报, 2013, 71, 934.)
(l) Han, Y.; Guo, J. B.; Chen, C. F. Chin. J. Chem. 2014, 32, 721.
(m) Yue, S. Y.; Zhou, Y. J.; Yao, Y.; Xue, M. Acta Chim. Sinica 2014, 72, 1053 (in Chinese). (岳诗雨, 周玉娟, 姚勇, 薛敏, 化学学报, 2014, 72, 1053.)
[2] (a) Dong, S. Y.; Luo, Y.; Yan, X. Z.; Zheng, B.; Ding, X.; Yu, Y. H.; Ma, Z.; Zhao, Q. L.; Huang, F. H. Angew. Chem., Int. Ed. 2011, 50, 1905.
(b) Zhang, M. M.; Xu, D. H.; Yan, X. Z.; Chen, J. Z.; Dong, S. Y.; Zheng, B.; Huang, F. H. Angew. Chem., Int. Ed. 2012, 51, 7011.
(c) Yan, X. Z.; Xu, D. H.; Chi, X. D.; Chen, J. Z.; Dong, S. Y.; Ding, X.; Yu, Y. H.; Huang, F. H. Adv. Mater. 2012, 24, 362.
(d) Yang, W. L.; Li, Y. J.; Zhang, J. H.; Chen, N.; Chen, S. H.; Liu, H. B.; Li, Y. L. Small 2012, 8, 2602.
(e) Yang, W. L.; Li, Y. J.; Liu, H. B.; Chi, L. F.; Li, Y. L. Small 2012, 8, 504.
(f) Li, Y. J.; Liu, H. B.; Li, Y. L. Curr. Org. Chem. 2011, 15, 97.
[3] (a) Wang, F.; Han, C. Y.; He, C. L.; Zhou, Q. Z.; Zhang, J. Q.; Wang, C.; Li, N.; Huang, F. H. J. Am. Chem. Soc. 2008, 130, 11254.
(b) Dong, S. Y.; Zheng, B.; Xu, D. H.; Yan, X. Z.; Zhang, M. M.; Huang, F. H. Adv. Mater. 2012, 24, 3191.
[4] Ashton, P. R.; Ballardini, R.; Balzani, V.; Baxter, I.; Credi, A.; Fyfe, M. C. T.; Gandolfi, M. T.; Gomez-Lopez, M.; Martine-Diaz, M.; Piersanti, A.; Spencer, N.; Stoddart, J. F.; Venturi, M.; White, A. J. P.; Williams, D. J. J. Am. Chem. Soc. 1998, 120, 1932.
[5] Ashton, P. R.; Baldoni, V.; Balzani, V.; Credi, A.; Hoffmann, H. D. A.; Martinez, D. M.; Raymo, F. M.; Stoddart, J. F.; Venturi, M. Chem. Eur. J. 2001, 16, 3482.
[6] (a) Badjic, J. D.; Balzani, V.; Credi, A.; Silvi, S.; Stoddart, J. F. Science 2004, 303, 1845.
(b) Badjic, J. D.; Ronconi, C. M.; Stoddart, J. F.; Balzani, V.; Silvi, S.; Credi, A. J. Am. Chem. Soc. 2006, 128, 1489.
[7] (a) Wu, J. S.; Leung, K. C. F.; Benítez, D.; Han, J. Y.; Cantrill, S. J.; Fang, L.; Stoddart, J. F. Angew. Chem., Int. Ed. 2008, 47, 7470.
(b) Fang, L.; Hmadeh, M.; Wu, J.; Olson, M. A.; Spruell, J. M.; Trabolsi, A.; Yang, Y. W.; Elhabiri, M.; Albrecht-Gary, A.; Stoddart, J. F. J. Am. Chem. Soc. 2009, 131, 7126.
[8] Du, G.; Moulin, E.; Jouault, N.; Buhler, E.; Giuseppone, N. Angew. Chem., Int. Ed. 2012, 51, 12504.
[9] Leigh, D. A.; Thomson, A. R. Tetrahedron. 2008, 64, 8411.
[10] Coutrot, F.; Eric, B. Chem. Eur. J. 2008, 14, 4784.
[11] Clavel, C.; Romuald, C.; Brabet, E.; Coutrot, F. Chem. Eur. J. 2013, 19, 2982.
[12] (a) Credit, A.; Balzani, V.; Langford, S. J.; Stoddart, J. F. J. Am. Chem. Soc. 1997, 119, 2679.
(b) Asakawa, M.; Iqbal, S.; Stoddart, J. F.; Tinker, N. D. Angew. Chem., Int. Ed. 1996, 35, 976.
(c) Ballardini, R.; Balzani, V.; Credi, A.; Gandolfi, M. T.; Langford, S. J.; Menzer, S.; Prodi, L.; Stoddart, J. F.; Venturi, M.; Williams, D. J. Angew. Chem., Int. Ed. 1996, 35, 978.
[13] Yan, X. Z.; Wu, X. J.; Wei, P. F.; Zhang, M. M.; Huang, F. H. Chem. Commun. 2012, 48, 8201.
[14] 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.
[15] Yang, W.; Li, Y. J.; Zhang, J. H.; Yu, Y. W.; Liu, T. F.; Liu, H. B.; Li, Y. L. Org. Biomol. Chem. 2011, 9, 6022.
[16] Yang, W.; Li, Y. J.; Zhang, J. H.; Chen, N.; Chen, S. H.; Liu, H. B.; Li, Y. L. J. Org. Chem. 2011, 76, 7750.
[17] Li, H.; Zhang, H.; Zhang, Q.; Zhang, Q. W.; Qu, D. H. Org. Lett. 2012, 14, 5900.
[18] Zhang, H.; Zhou, B.; Li, H.; Qu, D. H.; Tian, H. J. Org. Chem. 2013, 78, 2091.
[19] Jiang, W.; Han, M.; Zhang, H. Y.; Zhang, Z. J.; Liu, Y. Chem. Eur. J. 2009, 15, 9938.
[20] Jiang, Q.; Zhang, H. Y.; Han, M.; Ding, Z. J.; Liu, Y. Org. Lett. 2010, 12, 1728.
[21] Li, S. J.; Weng, G. H.; Zheng, B.; Yan, X. Z.; Wu, J.; Lin, W.; Chen, H. X.; Zhang, X. C. Eur. J. Org. Chem. 2012, 33, 6570.
[22] Bissell, R. A.; Cordova, E.; Kaifer, A. E.; Stoddart, J. F. Nature 1994, 369, 133.
[23] Leigh, D. A.; Thomson, A. R. Org. Lett. 2006, 8, 5377.
[24] Yen, M.; Li, W. S.; Lai, C. C.; Chao, I.; Chiu, S. H. Org. Lett. 2006, 8, 3223.
[25] Zhou, W.; Li, J.; He, X.; Li, C.; Lv, J.; Li, Y.; Wang, S.; Liu, H.; Zhu, D. Chem. Eur. J. 2008, 14, 754.
[26] Zheng, H. Y.; Zhou, W. D.; Lv, J.; Yin, X. D.; Li, Y. J.; Liu, H. B.; Li, Y. L. Chem. Eur. J. 2009, 15, 13253.
[27] Zhao, Y. J.; Li, Y. J.; Lai, S. W.; Yang, J.; Liu, C.; Liu, H. B.; Che, C. M.; Li, Y. L. Org. Biomol. Chem. 2011, 9, 7500.
[28] Huang, F. H.; Switek, K. A.; Gibson, H. W. Chem. Commun. 2005, 9, 3655.
[29] Zhang, Z. J.; Zhang, Y. M.; Liu, Y. J. Org. Chem. 2011, 76, 4682.
[30] iang, Y.; Guo, J.; Chen, C. Org. Lett. 2010, 12, 4248.
[31] Hu, S. Z.; Chen, C. F. Chem. Eur. J. 2011, 17, 5424.
[32] Khashab, N. M.; Trabolsi, A.; Lau, Y. A.; Ambrogio, M. W.; Friedman, D. C.; Khatib, H. A.; Zink, J. I.; Stoddart, J. F. Eur. J. Org. Chem. 2009, 11, 1669.
[33] Khashab, N. M.; Belowich, M. E.; Trabolsi, A.; Friedman, D. C.; Valente, C.; Lau, Y.; Khatib, H. A.; Zink, J. I.; Stoddart, J. F. Chem. Commun. 2009, 36, 5371.
[34] Angelos, S.; Khashab, N. M.; Yang, Y. W.; Trabolsi, A.; Khatib, H. A.; Stoddart, J. F.; Zink, J. I. J. Am. Chem. Soc. 2009, 131, 12912.
[35] Thomas, C. R.; Ferris, D. P.; Lee, J. H.; Choi, E.; Cho, M. H.; Kim, E. S.; Stoddart, J. F.; Shin, J. S.; Cheon, J.; Zink, J. I. J. Am. Chem. Soc. 2009, 132, 10623.
[36] Zhao, Y. L.; Li, Z.; Kabehie, S.; Botros, Y. Y.; Stoddart, J. F.; Zink, J. I. J. Am. Chem. Soc. 2009, 132, 13016.
[37] Meng, H.; Xue, M.; Xia, T.; Zhao, Y. L.; Tamanoi, F.; Stoddart, J. F.; Zink, J. I.; Nel, A. E. J. Am. Chem. Soc. 2010, 132, 12690.
[38] Boyle, M. M.; Smaldone, R. A.; Whalley, A. C.; Ambrogio, M. W.; Botros, Y. Y.; Stoddart, J. F. Chem. Sci. 2011, 2, 204.
[39] Ambrogio, M. W.; Thomas, C. R.; Zhao, Y. L.; Zink, J. I.; Stoddart, J. F. Acc. Chem. Res. 2011, 44, 903.
[40] (a) Yan, X.; Wang, F.; Zheng, B.; Huang, F. Chem. Soc. Rev. 2012, 41, 6042.
(b) Yan, X.; Li, S.; Pollock, B. J.; Cook, T. R.; Chen, J.; Zhang, Y.; Ji, X.; Yu, Y.; Huang, F.; Stang, P. J. Proc. Natl. Acad. Sci. U. S. A. 2013, 110, 15585.
(c) Li, S.; Weng, G.-H.; Lin, W.; Sun, Z.-B.; Zhou, M.; Zhu, B.; Ye, Y.; Wu, J. Polym. Chem. 2014, 5, 3994.
(d) Wei, P.; Li, S.; Zhang, Y.; Yu, Y.; Yan, X. Polym. Chem. 2014, 5, 3972.
[41] Fahrenbach, A. C.; Warren, S. C.; Incorvati, J. T.; Avestro, A. J.; Barnes, J. C.; Stoddart, J. F.; Grzybowski, B. A. Adv. Mater. 2013, 25, 331.
[42] Wang, F.; Zhang, J. Q.; Ding, X.; Dong, S. Y.; Liu, M.; Zheng, B.; Li, S. J.; Wu, L.; Yu, Y. H.; Gibson, H. W.; Huang, F. H. Angew. Chem., Int. Ed. 2010, 49, 1090.
[43] Ji, X. F.; Yao, Y.; Li, J. Y.; Yan, X. Z.; Huang, F. H. J. Am. Chem. Soc. 2013, 135, 74.
/
〈 |
|
〉 |