Study on the Complexation Properties of Promellitic Diimide- Extended Pillar[6]aren and Carboxylate Guests

doi:10.6023/cjoc202206018

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (1): 352-356.DOI: 10.6023/cjoc202206018 Previous Articles Next Articles

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均苯四甲酸二酰亚胺拓展柱[6]芳烃与羧酸盐客体分子的络合性能研究

程璐^a, 曾飞^b^,^*(), 王小峰^a^,^*()

a 南华大学化学化工学院湖南衡阳 421001
b 湖南科技学院化学与生物工程学院湖南永州 425199

收稿日期:2022-06-13 修回日期:2022-07-22 发布日期:2022-08-17
通讯作者: 曾飞, 王小峰
基金资助:
国家自然科学基金(21602055)

Study on the Complexation Properties of Promellitic Diimide- Extended Pillar[6]aren and Carboxylate Guests

Lu Cheng^a, Fei Zeng^b(), Xiaofeng Wang^a()

a School of Chemistry and Chemical Engineering, University of South China, Hengyang, Hunan 421001
b College of Chemical and Biological Engineering, Hunan University of Science and Engineering, Yongzhou, Hunan 425199

Received:2022-06-13 Revised:2022-07-22 Published:2022-08-17
Contact: Fei Zeng, Xiaofeng Wang
Supported by:
National Natural Science Foundation of China(21602055)

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Abstract

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.

Key words: pillararen, pyromellitic diimide, acid-base controlled, host-guest chemistry

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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.

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Fig. & Tab. 6

Figure 1. Chemical structures and proton designations of host 1 and guests G1~G5, and calculated potential profile of 1

Figure 2. Partial 1H NMR spectra (400 MHz, 298 K) in CDCl3 (a) Free 1, (b) 1 and 2.0 equiv. of G1, and (c) free G1. [1]0=4.0 mmol/L

Figure 3. Partial 1H NMR spectra (400 MHz, 298 K) in CDCl3 (a) Free 1, (b) 1 and 2.0 equiv. of G4, and (c) free G4. [1]0=4.0 mmol/L

Complex	Stoichiometry (H/G)	K_a1/(L•mol^–1)	K_a2/(L•mol^–1)	Cooperativity factor α^a
1•2G₁	1∶2	(2.68±0.04)×10⁴	(0.08±0.05)×10²	0.001
1•2G₂	1∶2	(2.33±0.09)×10⁴	(0.38±0.09)×10²	0.007
1•2G₃	1∶2	(3.26±0.03)×10³	(0.18±0.02)×10²	0.022
1•2G₄	1∶2	(8.20±0.58)×10²	(1.10±0.11)×10²	0.537
1•2G₅	1∶2	(3.78±0.25)×10³	(2.68±0.05)×10³	2.836

Table 1. Summary of the stoichiometries and association constants of the complexes

Figure 4. Partial 1H NMR spectra (400 MHz, 298 K) in CDCl3 (a) 1 and 2.0 equiv. of G1, (b) after addition of 2.0 μL of DCl (w=20%) to a, and (c) after addition of 1.0 μL of NaOD (w=40%) to b. [1]0=4.0 mmol/L

Figure 5. Structure of 1?2G2 optimized by Gaussian 09

References 15

[1]	(a) Schrader, T.; Hamilton, A. D. Functional Synthetic Receptors, Wiley-VCH, Weinheim, Germany, 2005.
	(b) Liu, Y.; You, C. C.; Zhang, H. Y. Supramolecular Chemistry, Nankai University Publication, Tianjin, 2001. (in Chinese)
	(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. doi: 10.1007/s11425-017-9089-8
	(b) Han, Y.; Meng, Z.; Ma, Y.-X.; Chen, C.-F. Acc. Chem. Res. 2014, 47, 2026. doi: 10.1021/ar5000677
	(c) Liu, Z.; Nalluri, S. K. M.; Stoddart, J. F. Chem. Soc. Rev. 2017, 46, 2459. doi: 10.1039/C7CS00185A
	(d) Wu, J.-R.; Yang, Y.-W. Chem. Commun. 2019, 55, 1533. doi: 10.1039/C8CC09374A
	(e) Wu, J.-R.; Yang, Y.-W. Angew. Chem., Int. Ed. 2020, 60, 1690. doi: 10.1002/anie.202006999
[4]	(a) Ogoshi, T.; Kanai, S.; Fujinami, S.; Yamagishi, T.-A.; Nakamoto, Y. J. Am. Chem. Soc. 2008, 130, 5022. doi: 10.1021/ja711260m
	(b) Cao, D.; Kou, Y.; Liang, J.; Chen, Z.; Wang, L.; Meier, H. Angew. Chem., Int. Ed. 2009, 48, 9721. doi: 10.1002/anie.200904765
	(c) Ogoshi, T.; Yamagishi, T. A.; Nakamoto, Y. Chem. Rev. 2016, 116, 7937. doi: 10.1021/acs.chemrev.5b00765
	(d) Kakuta, T.; Yamagishi, T.-A.; Ogoshi, T. Acc. Chem. Res. 2018, 51, 1656. doi: 10.1021/acs.accounts.8b00157
	(e) Wang, J.-H.; Feng, H. T.; Zheng, Y.-S. Chem. Commun. 2014, 50, 11407. doi: 10.1039/C4CC05189K
[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. doi: 10.1021/jacs.9b12216
[6]	(a) Han, X.-N.; Han, Y.; Chen, C.-F. J. Am. Chem. Soc. 2020, 142, 8262. doi: 10.1021/jacs.0c00624
	(b) Han, X.-N.; Zong, Q.-S.; Han, Y.; Chen, C.-F. CCS Chem. 2022, 4, 318. doi: 10.31635/ccschem.021.202100870
[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. doi: 10.1039/C4SC02422B
	(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. doi: 10.1002/anie.201905563
	(c) Ma, J.; Deng, H.; Ma, S.; Li, J.; Jia, X.; Li, C. Chem. Commun. 2015, 51, 6621. doi: 10.1039/C5CC01470K
[8]	(a) Huang, G.-B.; Wang, S.-H.; Ke, H.; Yang, L.-P.; Jiang, W. J. Am. Chem. Soc. 2016, 138, 14550. doi: 10.1021/jacs.6b09472 pmid: 28609613
	(b) Wang, L.-L.; Chen, Z.; Liu, W.-E.; Ke, H.; Wang, S.-H.; Jiang, W. J. Am. Chem. Soc. 2017, 139, 8436. doi: 10.1021/jacs.7b05021 pmid: 28609613
	(c) He, Z.; Yang, X.; Jiang, W. Org. Lett. 2015, 17, 3880. doi: 10.1021/acs.orglett.5b01871 pmid: 28609613
[9]	(a) Guo, Q.-H.; Zhao, L.; Wang, M.-X. Angew. Chem., Int. Ed. 2015, 54, 8386. doi: 10.1002/anie.201503179
	(b) Guo, S.-Y.; Guo, Q.-H.; Tong, S.; Wang, M.-X. Angew. Chem., Int. Ed. 2020, 59, 8078. doi: 10.1002/anie.201915839
	(c) Guo, Q.-H.; Fu, Z.-D.; Zhao, L.; Wang, M.-X. Angew. Chem., Int. Ed. 2014, 53, 13548. doi: 10.1002/anie.201407670
[10]	(a) Shi, Q.; Chen, C.-F. Org. Lett. 2017, 19, 3175. doi: 10.1021/acs.orglett.7b01296
	(b) Zhang, G.-W.; Li, P.-F.; Meng, Z.; Wang, H.-X.; Han, Y.; Chen, C.-F. Angew. Chem., Int. Ed. 2016, 55, 5304. doi: 10.1002/anie.201600911
	(c) Shi, Q.; Chen, C.-F. Chem. Sci. 2019, 10, 2529. doi: 10.1039/C8SC05469J
[11]	(a) Lei, S.-N.; Xiao, H.; Zeng, Y.; Tung, C.-H.; Wu, L.-Z.; Cong, H. Angew. Chem., Int. Ed. 2020, 59, 10059. doi: 10.1002/anie.201913340
	(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. doi: 10.1002/anie.201913055
	(c) Wang, J. Q.; Han, Y.; Chen, C.-F. Chem. Commun. 2021, 57, 3987. doi: 10.1039/D1CC00916H
	(d) Li, J.; Zhou, H.-Y.; Han, Y.; Chen, C.-F. Angew. Chem., Int. Ed. 2021, 60, 21927. doi: 10.1002/anie.202108209
	(e) Wu, J.-R.; Mu, A. U.; Li, B.; Wang, C. Y.; Fang, L.; Yang, Y.-W. Angew. Chem., Int. Ed. 2018, 57, 9853. doi: 10.1002/anie.201805980
	(f) Wu, J.-R.; Yang, Y.-W. CCS Chem. 2020, 2, 836.
	(g) Wu, J.-R.; Yang, Y.-W. J. Am. Chem. Soc. 2019, 141, 12280. doi: 10.1021/jacs.9b03559
	(h) Wu, J.-R.; Cai, Z.; Wu, G.; Dai, D.; Liu, Y.-Q.; Yang, Y.-W. J. Am. Chem. Soc. 2021, 143, 20395. doi: 10.1021/jacs.1c10139
	(i) Yang, J.; Yang, Y.-W. Small 2020 16, 2003490.
	(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. doi: 10.1038/nchem.597
[13]	(a) Gao, B.; Tan, L.-L.; Song, N.; Li, K.; Yang, Y.-W. Chem. Commun. 2016, 52, 5804. doi: 10.1039/C6CC01892K
	(b) Wu, J.-R.; Wang, C.-Y.; Tao, Y.-C.; Wang, Y.; Li, C.; Yang, Y.-W. Eur. J. Org. Chem. 2018, 2018, 1321. doi: 10.1002/ejoc.201800112
	(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. doi: 10.1021/jacs.9b01546
	(d) Yang, J.; Dai, D.; Ma, L.; Yang, Y.-W. Chin. Chem. Lett. 2021, 32, 729. doi: 10.1016/j.cclet.2020.08.035
	(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. doi: 10.1002/anie.202015162
[14]	Zeng, F.; Chen, L.; Ou, G. C.; Tang, L. L.; Ding, M. H. J. Org. Chem. 2022, 87, 3863. doi: 10.1021/acs.joc.1c03096
[15]	http://supramolecular.org./.

均苯四甲酸二酰亚胺拓展柱[6]芳烃与羧酸盐客体分子的络合性能研究

Study on the Complexation Properties of Promellitic Diimide- Extended Pillar[6]aren and Carboxylate Guests

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