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

  • 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.
  • 加载中
    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

  • 加载中
    1. [1]

      LIU Zhi-LianYANG Xiao-FengZHENG Lu-YiCUI YuWANG 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 JianZhu TaoFu Xiao-YiLiu 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]

      MA MingguangWEI Yunxia . Fabrication of Solid Phase Microextraction Fibers of Titanium Wires and Its Application. Chinese Journal of Applied Chemistry, 2020, 37(2): 218-226. doi: 10.11944/j.issn.1000-0518.2020.02.190235

    4. [4]

      Qian XinmingDu HuiLÜ HonghuiLiu FengqiBai YubaiLi TiejinTang 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]

      FAN Zhong-XiangHUANG Jian-Hua . Dissipative Particle Dynamics Simulation on Aggregation of Rod-Coil-Rod Triblock Copolymer in Dilute Solution. Acta Physico-Chimica Sinica, 2014, 30(3): 408-412. doi: 10.3866/PKU.WHXB201312271

    6. [6]

      Li JingHan YingChen Chuanfeng . Recent Advances in Novel Macrocyclic Arenes. Chinese Journal of Organic Chemistry, 2020, 40(11): 3714-3737. doi: 10.6023/cjoc202005007

    7. [7]

      Zhang RunmiaoWang ChenweiSun JingYan ChaoguoYao Yong . Design and Construction of Pillar[5]arene-Based Bis-[1]rotaxane. Chinese Journal of Organic Chemistry, 2019, 39(12): 3483-3489. doi: 10.6023/cjoc201906006

    8. [8]

      Chen JinfaLiu XiHan BingbingDing JindongZhang YoumingLin QiYao HongWei Taibao . Preparation and Properties of Supramolecular Organogel Based on Iodine-Functionalized Pillar[5]arene. Chinese Journal of Organic Chemistry, 2018, 38(10): 2741-2746. doi: 10.6023/cjoc201805003

    9. [9]

      Qingqing ZhouWengui DuanLuzhi LiuYan Huang . Construction and Antitumor Activity of Supramolecular Nano Drug Delivery System Based on Amphiphilic Pillar[5]arene. Chemistry, 2021, 84(5): 460-466.

    10. [10]

      CHENG LinWANG 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-YuQIN Chuan-GuangZHANG Qiu-YuZHAO WenZHANG Rui-JieLI 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 ShaoyanLU YaoHUANG 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-YanWANG JunPENG Chun-YunSUN De-HuiSUN Li-NingGUO Jun-FangZHANG 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-TangHu Rui-ShengZhu Zi-HuaZhu TaoLiu 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]

      CAI HongWU Guang-WeiLAI Jia-LiCHEN Jin-PingCHEN Yan-FeiLI Dan . Selective Adsorption of CO2 by Biological Metal-Organic Framework ZnBTCA. Chinese Journal of Inorganic Chemistry, 2019, 35(11): 2083-2088. doi: 10.11862/CJIC.2019.236

    19. [19]

      Yao HuanSun JiaonanKe HuaYang LiupanLi JiarongJiang 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 JianZhu TaoZhang XuLiu 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

Metrics
  • PDF Downloads(13)
  • Abstract views(815)
  • HTML views(98)

通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return