β-环糊精与18-冠-6超分子包合物的形成、结构和热降解

doi:10.3866/PKU.WHXB20110727

Abstract

Abstract:

The formation of a 1:1 supramolecular complex between β-cyclodextrin (β-CD) and 18- crown-6 (18C6) by simply mixing them was confirmed by elemental analysis, ¹H nuclear magnetic resonance (¹H NMR) and electrospray ionization mass spectrometry. The probable interaction sites between these species were determined by two-dimensional rotating frame nuclear Overhauser effect spectroscopy (ROESY), which showed that 18C6 tended to be located on the narrow end of the cavity of β-CD. Also, the degradation process including the degree of degradation and the degradation products of the complex was carefully compared with those of β-CD and 18C6 through thermogravimetric analysis and gas chromatography coupled to time-of-flight mass spectrometry. The experimental data indicated that the presence of 18C6 resulted in an earlier degradation of β-CD. Furthermore, the relative abundance of larger fragments from the degradation process of the two components was reduced drastically because of an intermolecular interaction. These results strongly indicate that a supramolecular complex can be constructed using the flexible macrocyclic molecule 18C6 as a guest and the rigid macrocyclic molecule β-CD as the host via molecular assembly between them.

Key words: β-Cyclodextrin, 18-crown-6, Nclusion complex, Intermolecular interaction, Supramolecule, Molecular assembly

Click here to download Supporting Info

ZHU Lin-Hong, SONG Le-Xin, CHEN Jie, YANG Jing, WANG Mang. Formation, Structure and Thermal Degradation of the Supramolecular Complex between β-Cyclodextrin and 18-Crown-6[J].Acta Phys. -Chim. Sin., 2011, 27(07): 1579-1586.

References

(1) Liu,Y.;You, C. C.; Zhang, H.Y. Supramolecular Chemistry— Molecular Recognition and Assembly of Synthetic Receptor; Nankai University Publishers: Tianjin, 2000; pp 191-239. [刘育, 尤长城, 张衡益. 超分子化学—合成受体的分子识别与组装. 天津: 南开大学出版社, 2000: 191-239.]
(2) Tong, L. H.; Shen, B. J. Physical Methods in Supramolecular Chemistry Study; Science Press: Beijing, 2004; pp 10-14. [童林荟, 申宝剑. 超分子化学研究中的物理方法. 北京: 科学出版社, 2004: 10-14.]
(3) Jiang, B. P.; Guo, D. S.; Liu, Y. J. Org. Chem. 2010, 75, 7258.
(4) Song, L. X.; Bai, L.; Xu, X. M.; He, J.; Pan, S. Z. Coord. Chem. Rev. 2009, 253, 1276.
(5) Chen, Y.; Li, F.; Liu, B.W.; Jiang, B. P.; Zhang, H. Y.;Wang, L. H.; Liu, Y. J. Phys. Chem. B 2010, 114, 16147.
(6) Farruggia, G.; Lotti, S.; Lombardo, M.; Marraccini, C.; Petruzziello, D.; Prodi, L.; Sgarzi, M.; Trombini, C.; Zaccheroni, N. J. Org. Chem. 2010, 75, 6275.
(7) Xu, P.; Song, L. X. Acta Phys.- Chim. Sin. 2008, 24, 2214. [徐鹏, 宋乐新. 物理化学学报, 2008, 24, 2214.]
(8) Song, L. X.;Wang, H. M.; Guo, X. Q.; Bai, L. J. Org. Chem. 2008, 73, 8305.
(9) Wang, T.; Chipot, C.; Shao, X. G.; Cai,W. S. Langmuir 2011, 27, 91.
(10) Wu, Q. H.; Zhu, M. Z.;Wei, S. J.; Song, K. S.; Liu, L.; Guo, Q. X. J. Incl. Phenom. Macrocycl. Chem. 2005, 52, 93.
(11) Wang, T.; Cai,W. S.; Shao, X. G. Prog. Chem. 2010, 22, 803.
(12) Song, L. X.; Yang, J.; Bai, L.; Du, F. Y.; Chen, J.;Wang, M. Inorg. Chem. 2011, 50, 1682.
(13) Liu, P.; Zhang, D. J.; Zhan, J. H. J. Phys. Chem. A 2010, 114, 13122.
(14) Hu, J.; Shao, D. D.; Chen, C. L.; Sheng, G. D.; Li, J. X.;Wang, X. K.; Nagatsu, M. J. Phys. Chem. B 2010, 114, 6679.
(15) Yu, M. A.; Chen, Y.; Zhang, N.; Liu, Y. Org. Biomol. Chem. 2010, 8, 4148.
(16) Hao, A. Y.; Tong, L. H.; Gao, X. M.; Zhang, F. S. Acta Phys.- Chim. Sin. 1995, 11, 202. [郝爱友, 童林荟, 高兴明, 张复升. 物理化学学报, 1995, 11, 202.]
(17) Terekhova, I. V.; Romanova, A. O.; Kumeev, R. S.; Fedorov, M. V. J. Phys. Chem. B 2010, 114, 12607.
(18) Jin, Y.; Kim, H. J.; Lee, J. Y.; Lee, S. Y.; Shim,W. J.; Hong, S. H.; Lee, S. S. Inorg. Chem. 2010, 49, 10241.
(19) Wang, S.W.; Gao, B. J.; Gao, X. C.;Wang, L. Acta Phys.- Chim. Sin. 2010, 26, 927. [王世伟, 高保娇, 高学超, 王玲. 物理化学学报, 2010, 26, 927.]
(20) Moorthy, J. N.; Natarajan, P. Chem.-Eur. J. 2010, 16, 7796.
(21) Huang, K.; Zhang, X. T.; Armstrong, D.W. J. Chromatogr. A 2010, 1217, 5261.
(22) Gong, X. Y.; Dobrunz, D.; Kumin, M.;Wiesner, M.; Revell, J. D.; Wennemers, H.; Hauser, P. C. J. Sep. Sci. 2008, 31, 565.
(23) V?gtle, F.; Müller,W. M. Angew. Chem. Int. Edit. Engl. 1979, 18, 623.
(24) Kamitori, S.; Hirotsu, K.; Higuchi, T. J. Am. Chem. Soc. 1987, 109, 2409.
(25) Gierczyk, B.; Nowak-Wydra, B.; Schroeder, G.; Pankiewicz, R. Magn. Reson. Chem. 2010, 48, 471.
(26) Song, L. X.; Xu, P. J. Phys. Chem. A 2008, 112, 11341.
(27) Marreto, R. N.; Almeida, E. E. C. V.; Alves, P. B.; Niculau, E. S.; Nunes, R. S.; Matos, C. R. S.; Araujo, A. A. S. Thermochim. Acta 2008, 475, 53.
(28) Song, L. X.; Du, F. Y.; Guo, X. Q.; Pan, S. Z. J. Phys. Chem. B 2010, 114, 1738.
(29) Gabelica, V.; Galic, N.; De Pauw, E. J. Am. Soc. Mass Spectrom. 2002, 13, 946.
(30) Arakawa, R.; Yamaguchi, T.; Takahashi, A. J. Am. Soc. Mass Spectrom. 2003, 14, 1116.
(31) Yu, Z.; Cui, M.; Yan, C. Y.; Song, F. R.; Liu, Z. Q.; Liu, S. Y. Rapid Commun. Mass Spectrom. 2007, 21, 683.
(32) Bai, L.; Song, L. X.;Wang, M.; Zhu, L. H. Chin. J. Chem. Phys. 2010, 23, 117. [柏雷, 宋乐新, 王莽, 朱林红. 化学物理学报, 2010, 23, 117.]
(33) Song, L. X.;Wang, M.; Dang, Z.; Du, F. Y. J. Phys. Chem. B 2010, 114, 3404.
(34) Wang, Y. H.; Zhu, M. Z.; Ding, X. Y.; Ye, J. P.; Liu, L.; Guo, Q. X. J. Phys. Chem. B 2003, 107, 14087.
(35) Akutagawa, T.; Sato, D.; Ye, Q.; Endo, T.; Noro, S. I.; Takeda, S.; Nakamura, T. Dalton T. 2010, 39, 8219.
(36) Perez-Tejeda, P.; Conejero, S.; Burgos, F. S.; Marchena, M. J. Phys. Chem. B 2010, 114, 9094.
(37) Xu, P.; Song, L. X.;Wang, H. M. Thermochim. Acta 2008, 469, 36.

[1]	Yu HE,Yi-Bo WANG. B972-PFD: A High Accuracy Density Functional Method for Dispersion Correction [J]. Acta Phys. -Chim. Sin., 2017, 33(6): 1149-1159.
[2]	Rui GUO,Jialin ZHANG,Songtao ZHAO,Xiaojiang YU,Shu ZHONG,Shuo SUN,Zhenyu LI,Wei CHEN. LT-STM Investigation of the Self-Assembled F₁₆CuPc-Corannulene Binary System on Ag (111) and Grap [J]. Acta Phys. -Chim. Sin., 2017, 33(3): 627-632.
[3]	Yue-Hong WANG,Xiao-Yan LI,Yan-Li ZENG,Ling-Peng MENG,Xue-Ying ZHANG. Topological Analyses of Electron Density on π-hole Pnicogen Bonds in PO₂X…PX₃/PH₂X (X = F, Cl, Br, CH₃, NH₂) Complexes [J]. Acta Phys. -Chim. Sin., 2016, 32(3): 671-682.
[4]	WANG Ying, YI Hai-Bo, LI Hui-Ji, DAI Qian, CAO Zhi-Wei, LU Yang. Effects of Interactions between Ions and Alanine Polar Groups on Alanine Associations in Saline Solution: Density Functional Theory and Molecular Dynamics Simulation [J]. Acta Phys. -Chim. Sin., 2015, 31(6): 1035-1044.
[5]	QIAN Hai-Cheng, KANWAL Shahid, JIA Qing-Zhu, WANG Qiang, JI Hui-Fen, ZHU Zhi-Chen, XIA Shu-Qian, MA Pei-Sheng. Norm Index-Based Quantitative Structure-Activity Relationship to Predict β-Cyclodextrin Complex Binding Constants [J]. Acta Phys. -Chim. Sin., 2015, 31(5): 893-898.
[6]	TAO Sha, YU Li-Juan, WU De-Yin, TIAN Zhong-Qun. Raman Spectra of Amino Wagging Vibrational Modes in p-π-Conjugated Molecules [J]. Acta Phys. -Chim. Sin., 2013, 29(08): 1609-1617.
[7]	LOU Peng-Xiao, WANG Yu-Jie, BAI Guang-Yue, FAN Chao-Ying, Wang Yi-Lin. Direct Evidence for the Energy of Weak Interactions between Surfactant Molecules Using High Sensitivity Isothermal Titration Calorimetry [J]. Acta Phys. -Chim. Sin., 2013, 29(07): 1401-1407.
[8]	SHAO Zhi-Cheng, SONG Le-Xin, TENG Yue, DANG Zheng, XIA Juan. Increased Water Solubility of Molybdenum Trioxide Induced by β-Cyclodextrin [J]. Acta Phys. -Chim. Sin., 2013, 29(03): 460-466.
[9]	ZHOU Liang-Chun, MENG Xiang-Guang, LI Jian-Mei, HU Wei, LIU Bo, DU Juan. Kinetics and Thermodynamics of Adsorption of Chlorophenols onto β-Cyclodextrin Modified Chitosan [J]. Acta Phys. -Chim. Sin., 2012, 28(07): 1615-1622.
[10]	SUN Tao, WANG Yi-Bo. Calculation of the Binding Energies of Different Types of Hydrogen Bonds Using GGA Density Functional and Its Long-Range, Empirical Dispersion Correction Methods [J]. Acta Phys. -Chim. Sin., 2011, 27(11): 2553-2558.
[11]	JIANG Jin-Qiang, JIANG Tao, ZHANG Cheng-Bang, CHENG Hao, LIU Xiao-Ya, ZHANG Sheng-Wen, CHEN Ming-Qing. Inclusion Behavior of β-Cyclodextrin and Amphiphilic Telechelic Polymer C-PDMAEMA [J]. Acta Phys. -Chim. Sin., 2011, 27(11): 2691-2696.
[12]	WU Ping-Fan, ZHANG Jin, WEI Yong-Ge. Controlled Assembly of Organoimido Derivatized Polyoxometalates [J]. Acta Phys. -Chim. Sin., 2010, 26(07): 1801-1810.
[13]	WANG Shi-Wei, GAO Bao-Jiao, GAO Xue-Chao, WANG Ling. Phase Transfer Catalytic Activity of Immobilized Dibenzo-18-Crown-6 for Butyl Benzoate Synthesis [J]. Acta Phys. -Chim. Sin., 2010, 26(04): 927-932.
[14]	GAO Yun-Yan, LIU Li-Hua, OU Zhi-Ze, LI Yi, YANG Guo-Qiang, WANG Xue-Song. Biological Activity of a Cholesterol Modified Fullerene/γ-Cyclodextrin Inclusion Complex [J]. Acta Phys. -Chim. Sin., 2010, 26(02): 495-501.
[15]	ZHANG Li, NIU Shu-Yun, JIN Jing, SUN Li-Ping, SHI Zhong-Feng, LI Lei. Preparation and Light-Induced Surface Electron Behavior of Ni(II) Based on Aromatic Polycarboxyl Acids [J]. Acta Phys. -Chim. Sin., 2009, 25(06): 1161-1166.

Formation, Structure and Thermal Degradation of the Supramolecular Complex between β-Cyclodextrin and 18-Crown-6

PDF

Like

Knowledge

Abstract

Supporting Info

Cite this article

share this article

References

Related Articles 15

Metrics

Recommended 0