Chinese Journal of Organic Chemistry >
Study on the Complexation Properties of Promellitic Diimide- Extended Pillar[6]aren and Carboxylate Guests
Received date: 2022-06-13
Revised date: 2022-07-22
Online published: 2022-08-18
Supported by
National Natural Science Foundation of China(21602055)
The complexation between the pyromellitic diimide-extended pillar[6]aren host and carboxylate guests in solution was investigated in detail. It was found that the host could form 1∶2 complexes with carboxylate salts in solution. Interestingly, the complexation and decomplexation of the complexes between the host and the guest could be achieved by changing the pH of the solution, and the process could also be observed by naked eye.
Lu Cheng , Fei Zeng , Xiaofeng Wang . Study on the Complexation Properties of Promellitic Diimide- Extended Pillar[6]aren and Carboxylate Guests[J]. Chinese Journal of Organic Chemistry, 2023 , 43(1) : 352 -356 . DOI: 10.6023/cjoc202206018
| [1] | (a) Schrader, T.; Hamilton, A. D. Functional Synthetic Receptors, Wiley-VCH, Weinheim, Germany, 2005. |
| [1] | (b) Liu, Y.; You, C. C.; Zhang, H. Y. Supramolecular Chemistry, Nankai University Publication, Tianjin, 2001. (in Chinese) |
| [1] | (刘育, 尤长城, 张衡益, 超分子化学, 南开大学出版社, 天津, 2001.) |
| [2] | Gloe, K. Macrocyclic Chemistry: Current Trends and Future Perspectives, Springer, Berlin, Germany, 2005. |
| [3] | (a) Wang, M.-X. Sci. China: Chem. 2018, 61, 993. |
| [3] | (b) Han, Y.; Meng, Z.; Ma, Y.-X.; Chen, C.-F. Acc. Chem. Res. 2014, 47, 2026. |
| [3] | (c) Liu, Z.; Nalluri, S. K. M.; Stoddart, J. F. Chem. Soc. Rev. 2017, 46, 2459. |
| [3] | (d) Wu, J.-R.; Yang, Y.-W. Chem. Commun. 2019, 55, 1533. |
| [3] | (e) Wu, J.-R.; Yang, Y.-W. Angew. Chem., Int. Ed. 2020, 60, 1690. |
| [4] | (a) Ogoshi, T.; Kanai, S.; Fujinami, S.; Yamagishi, T.-A.; Nakamoto, Y. J. Am. Chem. Soc. 2008, 130, 5022. |
| [4] | (b) Cao, D.; Kou, Y.; Liang, J.; Chen, Z.; Wang, L.; Meier, H. Angew. Chem., Int. Ed. 2009, 48, 9721. |
| [4] | (c) Ogoshi, T.; Yamagishi, T. A.; Nakamoto, Y. Chem. Rev. 2016, 116, 7937. |
| [4] | (d) Kakuta, T.; Yamagishi, T.-A.; Ogoshi, T. Acc. Chem. Res. 2018, 51, 1656. |
| [4] | (e) Wang, J.-H.; Feng, H. T.; Zheng, Y.-S. Chem. Commun. 2014, 50, 11407. |
| [5] | Della Sala, P.; Del Regno, R.; Talotta, C.; Capobianco, A.; Hickey, N.; Geremia, S.; De Rosa, M.; Spinella, A.; Soriente, A.; Neri, P.; Gaeta, C. J. Am. Chem. Soc. 2020, 142, 1752. |
| [6] | (a) Han, X.-N.; Han, Y.; Chen, C.-F. J. Am. Chem. Soc. 2020, 142, 8262. |
| [6] | (b) Han, X.-N.; Zong, Q.-S.; Han, Y.; Chen, C.-F. CCS Chem. 2022, 4, 318. |
| [7] | (a) Chen, H.; Fan, J.; Hu, X.; Ma, J.; Wang, S.; Li, J.; Yu, Y.; Jia, X.; Li, C. Chem. Sci. 2015, 6, 197. |
| [7] | (b) Wang, Y.; Xu, K.; Li, B.; Cui, L.; Li, J.; Jia, X.; Zhao, H.; Fang, J.; Li, C. Angew. Chem., Int. Ed. 2019, 58, 10281. |
| [7] | (c) Ma, J.; Deng, H.; Ma, S.; Li, J.; Jia, X.; Li, C. Chem. Commun. 2015, 51, 6621. |
| [8] | (a) Huang, G.-B.; Wang, S.-H.; Ke, H.; Yang, L.-P.; Jiang, W. J. Am. Chem. Soc. 2016, 138, 14550. |
| [8] | (b) Wang, L.-L.; Chen, Z.; Liu, W.-E.; Ke, H.; Wang, S.-H.; Jiang, W. J. Am. Chem. Soc. 2017, 139, 8436. |
| [8] | (c) He, Z.; Yang, X.; Jiang, W. Org. Lett. 2015, 17, 3880. |
| [9] | (a) Guo, Q.-H.; Zhao, L.; Wang, M.-X. Angew. Chem., Int. Ed. 2015, 54, 8386. |
| [9] | (b) Guo, S.-Y.; Guo, Q.-H.; Tong, S.; Wang, M.-X. Angew. Chem., Int. Ed. 2020, 59, 8078. |
| [9] | (c) Guo, Q.-H.; Fu, Z.-D.; Zhao, L.; Wang, M.-X. Angew. Chem., Int. Ed. 2014, 53, 13548. |
| [10] | (a) Shi, Q.; Chen, C.-F. Org. Lett. 2017, 19, 3175. |
| [10] | (b) Zhang, G.-W.; Li, P.-F.; Meng, Z.; Wang, H.-X.; Han, Y.; Chen, C.-F. Angew. Chem., Int. Ed. 2016, 55, 5304. |
| [10] | (c) Shi, Q.; Chen, C.-F. Chem. Sci. 2019, 10, 2529. |
| [11] | (a) Lei, S.-N.; Xiao, H.; Zeng, Y.; Tung, C.-H.; Wu, L.-Z.; Cong, H. Angew. Chem., Int. Ed. 2020, 59, 10059. |
| [11] | (b) Yang, W.; Samanta, K.; Wan, X.; Thikekar, T. U.; Chao, Y.; Li, S.; Du, K.; Xu, J.; Gao, Y.; Zuilhof, H.; Sue, A. C.-H. Angew. Chem., Int. Ed. 2020, 59, 3994. |
| [11] | (c) Wang, J. Q.; Han, Y.; Chen, C.-F. Chem. Commun. 2021, 57, 3987. |
| [11] | (d) Li, J.; Zhou, H.-Y.; Han, Y.; Chen, C.-F. Angew. Chem., Int. Ed. 2021, 60, 21927. |
| [11] | (e) Wu, J.-R.; Mu, A. U.; Li, B.; Wang, C. Y.; Fang, L.; Yang, Y.-W. Angew. Chem., Int. Ed. 2018, 57, 9853. |
| [11] | (f) Wu, J.-R.; Yang, Y.-W. CCS Chem. 2020, 2, 836. |
| [11] | (g) Wu, J.-R.; Yang, Y.-W. J. Am. Chem. Soc. 2019, 141, 12280. |
| [11] | (h) Wu, J.-R.; Cai, Z.; Wu, G.; Dai, D.; Liu, Y.-Q.; Yang, Y.-W. J. Am. Chem. Soc. 2021, 143, 20395. |
| [11] | (i) Yang, J.; Yang, Y.-W. Small 2020 16, 2003490. |
| [11] | (j) Wu, J.-R.; Wu, G.; Li, D.; Dai, D.; Yang, Y.-W. Sci. Adv. 2022, 8, eabo2255. |
| [12] | Gong, H.-Y.; Rambo, B. M.; Karnas, E.; Lynch, V. M.; Sessler, J. L. Nat. Chem. 2010, 2, 406. |
| [13] | (a) Gao, B.; Tan, L.-L.; Song, N.; Li, K.; Yang, Y.-W. Chem. Commun. 2016, 52, 5804. |
| [13] | (b) Wu, J.-R.; Wang, C.-Y.; Tao, Y.-C.; Wang, Y.; Li, C.; Yang, Y.-W. Eur. J. Org. Chem. 2018, 2018, 1321. |
| [13] | (c) Dai, D.; Li, Z.; Yang, J.; Wang, C.; Wu, J.-R.; Wang, Y.; Zhang, D.; Yang, Y.-W. J. Am. Chem. Soc. 2019, 141, 4756. |
| [13] | (d) Yang, J.; Dai, D.; Ma, L.; Yang, Y.-W. Chin. Chem. Lett. 2021, 32, 729. |
| [13] | (e) Dai, D.; Yang, J.; Zou, Y.-C.; Wu, J.-R.; Tan, L. L.; Wang, Y.; Li, B.; Lu, T.; Wang, B.; Yang, Y.-W. Angew. Chem., Int. Ed. 2021, 60, 8967. |
| [14] | Zeng, F.; Chen, L.; Ou, G. C.; Tang, L. L.; Ding, M. H. J. Org. Chem. 2022, 87, 3863. |
| [15] | http://supramolecular.org./. |
/
| 〈 |
|
〉 |
