Host-Guest Interactions of Cyclopentanocucurbit[6]uril with Alkyl Imidazolium Hydrochlorides

Abstract

The host-guest interactions between cyclopentanocucurbit-[6]uril(CyP₆Q[6]) as host and six alkyl imidazolium hydrochloride as guests(g1, g2, g3, g4, g5, and g6) have been studied by various techniques, such as ¹H NMR spectroscopy, isothermal titration calorimetry, mass spectrometry, and single-crystal X-ray diffraction analysis. The experimental results showed that CyP₆Q[6] formed 1:1 inclusion complexes with each of guests g1–g6. The part of the guest entered the cavity of CyP₆Q[6] changes as the alkyl chain increases in length. It can be seen that the length of the alkyl chain plays a key role in determining the mode of host-guest interactions.

Keywords

Host-guest chemistry / Cucurbituril / Alkyl imidazolium salt / Inclusion complex

References

[1] Freeman W A, Mock W L, Shih N Y. J. Am. Chem. Soc., 1981, 103: 7367.

[2] Yang J, Shao L, Yuan J, Huang F. Chem. Commun., 201, 52: 12510.

[3] Li Q, Sun J, Zhou J, Hua B, Shao L, Huang F. Org. Chem. Front., 2018, 5: 1940.

[4] Li Q, Jie K, Huang F. Angew. Chem. Int. Ed., 2020, 59: 5355.

[5] Dong S, Zheng B, Wang F, Huang F. Acc. Chem. Res., 2014, 47: 1982.

[6] Kim K, Selvapalam N, Oh D H. J. Incl. Phenom. Macro., 2004, 50: 31.

[7] Day A, Arnold A P, Blanch R J, Snushall B. J. Org. Chem., 2001, 66: 8094.

[8] Day A I, Blanch R J, Arnold A P, Lorenzo S, Lewis G R, Dance I. Angew. Chem., 2002, 41: 275.

[9] Liu S, Zavalij P Y, Isaacs L. J. Am. Chem. Soc., 2005, 127: 16798.

[10] Xue S F, Zhu Q J, Ni X L, Tao Z. Angew. Chem. Int. Ed., 2013, 52: 7252.

[11] Flinn A, Hough G C, Stoddart J F, Williams D J. Angew. Chem. Int. Ed., 1992, 31: 1475.

[12] Zhao J H, Kim H J, Oh J H, Kim S Y, Lee J W, Sakamoto S, Yamaguchi K, Kim K. Angew. Chem., 2001, 113: 4363.

[13] Wu F, Wu L H, Xiao X, Zhang Y Q, Xue S F, Tao Z, Day A I. J. Org. Chem., 2012, 77: 606.

[14] Wu L H, Ni X L, Wu F, Zhang Y Q, Zhu Q J, Xue S F, Tao Z. J. Mol. Struct., 2009, 920: 183.

[15] Jon S Y, Selvapalam N, Oh D H, Kang J K, Kim S Y, Jeon Y J, Lee J W, Kim K. J. Am. Chem. Soc., 2003, 125: 10186.

[16] Isobe H, Sato S, Nakamura E. Org. Lett., 2002, 4: 1287.

[17] Ni X L, Xiao X, Cong H, Zhu Q J, Xue S F, Tao Z. Acc. Chem. Res., 2014, 47: 1386.

[18] Nikolova V, Velinova A, Dobrev S, Kircheva N, Angelova S, Dudev T. J. Phys. Chem. A, 2021, 125: 536.

[19] Prabodh A, Sinn S, Grimm L, Miskolczy Z, Megyesi M, Biczók L, Bräse S, Biedermann F. ChemComm, 2020, 56: 12327.

[20] Sowa A, Voskuhl J. Int. J. Pharm., 2020, 586: 119595.

[21] Ai Q, Jin L, Gong Z, Liang F. ACS Omega, 2020, 5: 10581.

[22] Mao W, Liao Y, Ma D. ChemComm, 2020, 56: 4192.

[23] Qu Y X, Lin R L, Zhang Y Q, Zhou K Z, Zhou Q D, Zhu Q J, Tao Z, Ma P H, Liu J X, Wei G. Org. Chem. Front., 2017, 4: 1799.

[24] Sojka M, Fojtu M, Fialova J, Masarik M, Necas M, Marek R. Inorg. Chem., 2019, 58: 10861.

[25] Feng X, Du H, Chen K, Xiao X, Luo S X, Xue S F, Zhang Y Q, Zhu Q J, Tao Z, Zhang X Y, Wei G. Cryst. Growth Des., 2010, 10: 2901.

[26] Lei W, Jiang G, Zhou Q, Hou Y, Zhang B, Cheng X, Wang X. Chemphyschem, 2013, 14: 1003.

[27] Hu Z, Sun D, Han X, Liu S. Chinese J. Org. Chem., 2020, 40(5): 1361.

[28] Sadhu B, Bandyopadhyay T, Sundararajan M. Inorg. Chem., 201, 55: 598.

[29] Qu Y X, Zhou K Z, Chen K, Zhang Y Q, Xiao X, Zhou Q D, Tao Z, Ma P H, Wei G. Inorg. Chem., 2018, 57: 7412.

[30] Cheng R X, Tian F Y, Zhang Y Q, Chen K, Zhu Q J, Tao Z. J. Mater. Sci., 2020, 55: 1.

[31] Jin Y M, Huang T H, Zhao W W, Yang X N, Meng Y, Ma P H. RSC Adv., 2020, 10: 37369.

[32] Mei L, Li F Z, Lan J H, Wang C Z, Xu C, Deng H, Wu Q Y, Hu K Q, Wang L, Chai Z F, Chen J, Gibson J K, Shi W Q. Nat. Commun., 2019, 10: 1532.

[33] Meng Y, Zhao W W, Zheng J, Jiang D F, Gao J, Jin Y M, Ma P H. RSC Adv., 2021, 11: 3470.

[34] Basiuk V A, Chuiko A A. J. Chromatogr. A, 1990, 521: 29.

[35] Daghir-Wojtkowiak E, Sylwia S, Buszewski B, Kaliszan R, Markuszewski M J. Anal. Methods, 2013, 6: 1189.

[36] Vicente F A, Lario L D, Pessoa A, Ventura S P M. Process Biochem., 201, 51: 528.

[37] Lívia N, Gyetvai G, László K, GézaNagy J. Biochem. Bioph. Meth., 200, 69: 121.

[38] Song S, Li H, Yang J, Guan S, Zhao S. J. Funct. Mater., 2018, 49: 1033.

[39] Tong J, Zhang D, Li K, Chen X, Qu Y. J. Chem. Thermodyn., 201, 101: 356.

[40] Gerasko O A, Samsonenko D G, Fedin V P. Russ. Chem. Rev., 2002, 71: 741.

[41] Lee J W, Samal S, Selvapalam N, Kim H J, Kim K. Acc. Chem. Res., 2003, 36: 621.

[42] Zhang X, Sun T, Ni X L. Org. Chem. Front., 2021, 8: 32.