Citation: Shi Haixiong, Cheng Xiaobin, Lin Qi, Yao Hong, Zhang Youming, Wei Taibao. Study on the Effect of Host-Guest Based on the Dimethoxy-pillar[5]arene and Benzazole Heterocyclic Compounds[J]. Chinese Journal of Organic Chemistry, ;2018, 38(7): 1718-1724. doi: 10.6023/cjoc201712037 shu

Study on the Effect of Host-Guest Based on the Dimethoxy-pillar[5]arene and Benzazole Heterocyclic Compounds

Shi Haixiong ^a,b ,
Cheng Xiaobin ^a ,
Lin Qi ^a ,
Yao Hong ^a ,
Zhang Youming ^a ,
Wei Taibao ^a,,

a.
Key Laboratory of Eco-Environment-Related Polymer Materials, Ministry of Education, Key Laboratory of Polymer Materials of Gansu Province, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070
b.
College of Chemical Engineering, Lanzhou University of Arts and Science, Lanzhou 730000

Corresponding author: Wei Taibao, weitaibao@126.com
Received Date: 26 December 2017
Revised Date: 14 March 2018
Available Online: 29 July 2018
Fund Project: the National Natural Science Foundation of China 21661018the National Natural Science Foundation of China 21574104Project supported by the National Natural Science Foundation of China (Nos. 21661018, 21662031, 21574104)the National Natural Science Foundation of China 21662031

Figures(5)

A host-guest system was successfully constructed from dimethoxypillar[5]arene (DMP5) and six guest molecules benzoazolidazole (G2), benzimidazole (G3) and benzothiazole (G1, G4, G5 and G6) via host-guest interactions and characterized by various techniques, including HRMS and ¹H NMR spectra. The result shows that heterocyclic compound was threaded into the cavity of pillar[5]arene to obtain host-guest system between DMpillar[5]arene and benzazole, forming inclusion complexes. Interestingly, the corresponding guest containing benzazole formed a stable host-guest complex with the same host. Moreover, the addition of guest compounds led to the effective reinforcement of the fluorescence intensity compared with the original guest species and the host (DMP5) that giving an additional support for the host-guest interaction based supramolecular assembly nature of the present system.
- pillar[5]arenes,
- host-guest chemistry,
- assembly,
- benzazole heterocyclic compounds
1. [1]
  Ogoshi, T.; Kanai, S.; Fujinami, S.; Yamagishi, T. A.; Nakamoto, Y. J. Am. Chem. Soc. 2008, 130, 5022. doi: 10.1021/ja711260m
2. [2]
  Cao, D.; Kou, Y.; Liang, J.; Chen, Z.; Wang, L.; Meier H. Angew. Chem., Int. Ed. 2009, 48, 9721. doi: 10.1002/anie.200904765
3. [3]
  Ma, Y.; Zhang, Z.; Ji, X.; Han, C.; He, J.; Abliz, Z.; Chen, W.; Huang, F. Eur. J. Org. Chem. 2011, 2011, 5331. doi: 10.1002/ejoc.201100698
4. [4]
  Han, C.; Zhang, Z.; Chi, X.; Zhang, M.; Yu, G.; Huang, F. Acta Chim. Sinica 2012, 70, 1775 (in Chinese).
5. [5]
  Yue, S.; Zhou, Y.; Yao, Y.; Xue, M. Acta Chim. Sinica 2014, 72, 1053 (in Chinese). doi: 10.3969/j.issn.0253-2409.2014.09.005
6. [6]
  Yang, Y. W.; Sun, Y. L.; Song, N. Acc. Chem. Res. 2014, 47, 1950. doi: 10.1021/ar500022f
7. [7]
  Zhang, H.; Liu, Z.; Xin, F.; Hao, A. Chin. J. Org. Chem. 2012, 32, 219 (in Chinese).
8. [8]
  Su, G.; Wu, D.; Li, Q.; Hou, J. Chin. J. Org. Chem. 2016, 36, 2130 (in Chinese).
9. [9]
  Li, C. Chem. Commun. 2014, 50, 12420. doi: 10.1039/C4CC03170A
10. [10]
  Yao, Y.; Xue, M.; Chen, J.; Zhang, M.; Huang, F. J. Am. Chem. Soc. 2012, 134, 15712. doi: 10.1021/ja3076617
11. [11]
  Si, W.; Chen, L.; Hu, X.-B.; Tang, G.; Chen, Z.; Hou, J.-L.; Li, Z.-T. Angew. Chem. 2011, 123, 12772. doi: 10.1002/ange.201106857
12. [12]
  Duan, Q.; Cao, Y.; Li, Y.; Hu, X.; Xiao, T.; Lin, C.; Pan, Y.; Wang, L. J. Am. Chem. Soc. 2013, 135, 10542. doi: 10.1021/ja405014r
13. [13]
  Jiang, B.; Wang, W.; Zhang, Y.; Lu, Y.; Zhang, C.-W.; Yin, G.-Q.; Zhao, X.-L.; Xu, L.; Tan, H.; Li, X.; Jin, G.-X.; Yang, H.-B. Angew. Chem., Int. Ed. 2017, 56, 14438. doi: 10.1002/anie.201707209
14. [14]
  Jiang, L.; Huang, X.; Chen, D.; Yan, H.; Li, X.; Du, X. Angew. Chem., Int. Ed. 2017, 56, 2655. doi: 10.1002/anie.201611973
15. [15]
  Wei, T.-B.; Chen, J.-F. Cheng, X.-B.; Li, H.; Han, B.-B.; Zhang, Y.-M.; Yao, H.; Lin, Q. Org. Chem. Front. 2017, 4, 210. doi: 10.1039/C6QO00569A
16. [16]
  Lin, Q.; Mao, P.-P.; Fan, Y.-Q.; Liu, L.; Liu, J.; Zhang, Y.-M.; Yao, H.; Wei, T.-B. Soft Matter 2017, 13, 7085. doi: 10.1039/C7SM01447C
17. [17]
  Wei, T.-B.; Chen, J.-F.; Cheng, X.-B.; Li, H.; Han, B.-B.; Yao, H.; Zhang, Y.-M.; Lin, Q. Polym. Chem. 2017, 8, 2005. doi: 10.1039/C7PY00335H
18. [18]
  Zhang, Y. M.; Shi, B. B.; Li, H.; Qu, W. J.; Gao, G. Y.; Lin, Q.; Yao, H.; Wei, T. B. Polym. Chem. 2014, 5, 4722. doi: 10.1039/C4PY00186A
19. [19]
  Lin, Q.; Jiang, X.-M.; Liu, L.; Chen, J.-F.; Zhang, Y.-M.; Yao, H.; Wei, T.-B. Soft Matter. 2017, 13, 7222. doi: 10.1039/C7SM01576C
20. [20]
  Lin, Q.; Fan, Y.-Q.; Mao, P.-P.; Liu, L.; Liu, J.; Zhang, Y.-M.; Yao, H.; Wei, T.-B. Chem.-Eur. J. 2018, 24, 777. doi: 10.1002/chem.201705107
21. [21]
  Lin, Q.; Zhong, K.-P.; Zhu, J.-H.; Ding, L.; Su, J.-X.; Yao, H.; Wei, T.-B.; Zhang, Y.-M. Macromolecules 2017, 50, 7863. doi: 10.1021/acs.macromol.7b01835
22. [22]
  Li, Z.-Y.; Zhang, Y.; Zhang, C.-W.; Chen, L.-J. Wang, C.; Tan, H.; Yu, Y.; Li, X.; Yang, H.-B. J. Am. Chem. Soc. 2014, 136, 8577. doi: 10.1021/ja413047r
23. [23]
  Zhang, C.-W.; Ou, B.; Yin, G.-Q.; Chen, L.-J.; Yang, H.-B. Acta Polym. Sinica 2017, (1), 71 (in Chinese).
24. [24]
  Strutt, N. L.; Zhang, H.; Schneebeli, S. T.; Stoddart, J. F. Acc. Chem. Res. 2014, 47, 2631. doi: 10.1021/ar500177d
25. [25]
  Ogoshi, T.; Yamagishi, T.; Nakamoto, Y. Chem. Rev. 2016, 116, 7937. doi: 10.1021/acs.chemrev.5b00765
26. [26]
  Wu, X.; Duan, Q.-P.; Ni, M.-F.; Hu, X.-Y.; Wang, L.-Y. Chin. J. Org. Chem. 2014, 34, 437 (in Chinese).
27. [27]
  Wang, Q.; Cheng, M.; Cao, Y.; Jiang, J.; Wang, L. Acta Chim. Sinica 2016, 74, 9 (in Chinese).
28. [28]
  Bai, D.; Wang, X.; Gao, Z.; Qiu, S.; Tao, Z.; Zhang, J.; Xiao, X. Chin. J. Org. Chem. 2017, 37, 2022 (in Chinese).
29. [29]
  Ogoshi, T.; Hashizume, M.; Yamagishi, T. A.; Nakamoto, Y. Chem. Commun. 2010, 46, 3708. doi: 10.1039/c0cc00348d
30. [30]
  Ma, Y.; Ji, X.; Xiang, F.; Chi, X.; Han, C.; He, J.; Abliz, Z.; Chen, W.; Huang, F. Chem. Commun. 2011, 47, 12340. doi: 10.1039/c1cc15660h
31. [31]
  Han, C.; Ma, F.; Zhang, Z.; Xia, B.; Yu, Y.; Huang, F. Org. Lett. 2010, 12, 4360. doi: 10.1021/ol1018344
32. [32]
  Li, C.; Chen, S.; Li, J.; Han, K.; Xu, M.; Hu, B.; Yu, Y.; Jia, X. Chem. Commun. 2011, 47, 11294. doi: 10.1039/c1cc14829j
33. [33]
  Liu, L.; Cao, D.; Jin, Y.; Tao, H.; Kou, Y.; Meier, H. Org. Biomol. Chem. 2011, 9, 7007. doi: 10.1039/c1ob05871a
34. [34]
  Shu, X.; Chen, S.; Li, J.; Chen, Z.; Weng, L.; Jia, X.; Li, C. Chem. Commun. 2012, 48, 2967. doi: 10.1039/c2cc00153e
35. [35]
  Liu, L.; Duan, W.; Kou, Y.; Wang, L.; Meier, H.; Cao, D. Chin. J. Chem. 2015, 33, 346. doi: 10.1002/cjoc.201400879
36. [36]
  Wu, G.-Y.; Shi, B.-B.; Lin, Q.; Li, H.; Zhang, Y.-M.; Yao, H.; Wei, T.-B. RSC Adv. 2015, 5, 4958. doi: 10.1039/C4RA08592B
37. [37]
  Lin, Q.; Liu, L.; Zheng, F.; Mao, P.-P.; Liu, J.; Zhang, Y.-M.; Yao, H.; Wei, T.-B. Tetrahedron 2017, 73, 5307. doi: 10.1016/j.tet.2017.07.028
38. [38]
  Lin, Q.; Zheng, F.; Liu, L.; Mao, P.-P.; Zhang, Y.-M.; Yao, H.; Wei, T.-B. RSC Adv. 2016, 6, 111928. doi: 10.1039/C6RA23878E
39. [39]
  Lin, Q.; Mao, P.-P.; Zheng, F.; Liu, L.; Liu, J.; Zhang, Y.-M.; Yao, H.; Wei, T.-B. New J. Chem. 2017, 41, 12172. doi: 10.1039/C7NJ02581E
40. [40]
  Lin, Q.; Lu, T.-T.; Zhu, X.; Wei, T.-B.; Li, H.; Zhang, Y.-M. Chem. Sci. 2016, 7, 5341. doi: 10.1039/C6SC00955G
41. [41]
  Chen, J.-F.; Lin, Q.; Zhang, Y.-M.; Yao, H.; Wei, T.-B. Chem. Commun. 2017, 53, 13296. doi: 10.1039/C7CC08365C
42. [42]
  Wei, T.-B.; Cheng, X.-B.; Li, H.; Zheng, F.; Lin, Q.; Yao, H.; Zhang, Y.-M. RSC Adv. 2016, 6, 20987. doi: 10.1039/C5RA26240B
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  LIU Zhi-Lian , YANG Xiao-Feng , ZHENG Lu-Yi , CUI Yu , WANG Zhi-Ling . Research Advances of Supramolecular Assemblies based on Pillar[5]arenes. Chinese Journal of Chemical Education, 2015, 36(2): 1-8. doi: 10.13884/j.1003-3807hxjy.2014040104
2. [2]
  Wang Jian , Zhu Tao , Fu Xiao-Yi , Liu Zhong-Fan . Study of Chemical Enhancement in SERS from Au Nanoparticles Assembly. Acta Physico-Chimica Sinica, 1998, 14(06): 485-489. doi: 10.3866/PKU.WHXB19980602
3. [3]
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4. [4]
  Qian Xinming , Du Hui , LÜ Honghui , Liu Fengqi , Bai Yubai , Li Tiejin , Tang Xinyi . Ordered Two-Dimensional Arrays from Nanometer Polymer Latex by Capillary Force Method. Chinese Journal of Applied Chemistry, 1999, 16(2): 51-55.
5. [5]
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6. [6]
  Li Jing , Han Ying , Chen Chuanfeng . Recent Advances in Novel Macrocyclic Arenes. Chinese Journal of Organic Chemistry, 2020, 40(11): 3714-3737. doi: 10.6023/cjoc202005007
7. [7]
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9. [9]
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10. [10]
  CHENG Lin , WANG Fengyang . Amphiphilic Mixed-Shell Polymeric Nanoparticles:Efficient Synthesis and Use as Template for Preparing Gold Nanoclusters. Chinese Journal of Applied Chemistry, 2011, 28(2): 149-153. doi: 10.3724/SP.J.1095.2011.00224
11. [11]
  WAGN Qiu-Yu , QIN Chuan-Guang , ZHANG Qiu-Yu , ZHAO Wen , ZHANG Rui-Jie , LI Yang . Immobilization of Papain by Layer-by-Layer Self-Assembly on Magnetic Polystyrene Microspheres. Chinese Journal of Applied Chemistry, 2009, 26(5): 557-561.
12. [12]
  Shasha Liu , Huixiang Li , Huizhi Fan , Jie Lei . Diversified Assembly and Application of Optical Fiber Spectrometer: An Instrumental Analysis Experiment. University Chemistry, 2020, 35(2): 64-69. doi: 10.3866/PKU.DXHX201906046
13. [13]
  MOU Shaoyan , LU Yao , HUANG Xiaoyi . Micro-fabrication of Nanosized SiO₂ Microspheres on Melamine-formaldehyde Resin. Chinese Journal of Applied Chemistry, 2011, 28(12): 1456-1458. doi: 10.3724/SP.J.1095.2011.00046
14. [14]
  GAO Shu-Yan , WANG Jun , PENG Chun-Yun , SUN De-Hui , SUN Li-Ning , GUO Jun-Fang , ZHANG Hong-Jie . Application of Langmuir-Blodgett Technique in Assembly of Nanoparticles. Chinese Journal of Applied Chemistry, 2005, 22(7): 697-702.
15. [15]
  Liu Shan-Tang , Hu Rui-Sheng , Zhu Zi-Hua , Zhu Tao , Liu Zhong-Fan . Reorganization of ld Nanoprticles in Self-Assembled Nanostructures. Acta Physico-Chimica Sinica, 2000, 16(04): 294-298. doi: 10.3866/PKU.WHXB20000402
16. [16]
  Peng Xiaoxia . Synthesis and Complexing Capacity of Two Triptycene-Based Molecular Tweezers. Chemistry, 2016, 79(5): 448-452.
17. [17]
  Peng Xiaoxia . Synthesis and Complexing Capacity of Two Triptycene-Based Molecular Tweezers. Chemistry, 2016, 79(5): 448-452.
18. [18]
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19. [19]
  Yao Huan , Sun Jiaonan , Ke Hua , Yang Liupan , Li Jiarong , Jiang Wei . Synthesis of Bis-naphthalene and Their Derivatives and Their Complexation with Organic Cation. Chinese Journal of Organic Chemistry, 2017, 37(3): 603-607. doi: 10.6023/cjoc201612033
20. [20]
  Wang Jian , Zhu Tao , Zhang Xu , Liu Zhong-Fan . The SERS Intensity vs the Size of Au Nanoparticles. Acta Physico-Chimica Sinica, 1999, 15(05): 476-480. doi: 10.3866/PKU.WHXB19990518

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