葫芦脲作为超分子纳米反应器/催化剂的研究

龚晚君; 赵智勇; 刘思敏*

doi:10.7536/PC160936

化学进展 ›› 2016, Vol. 28 ›› Issue (12) :1732-1742 DOI: 10.7536/PC160936

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葫芦脲作为超分子纳米反应器/催化剂的研究

龚晚君, 赵智勇, 刘思敏*

作者信息 +

Cucurbituril-Based Supramolecular Nanoreactors/Catalysts

Gong Wanjun, Zhao Zhiyong, Liu Simin*

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文章历史 +

摘要

葫芦脲是近年来获得广泛关注和长足发展的一种新型超分子主体化合物，其刚性的结构、疏水性的空腔及电负性的端口赋予其极为特殊的识别性质——对有机阳离子客体的高选择性和高亲合性。过去的十几年里，学者们利用其独特的性质将其应用在包括从基本的分子识别与组装到复杂的三维材料的制备以及药物传输及缓释等各个领域中。此外，创造性地将葫芦脲分子用于控制化学反应进程则成为了葫芦脲化学又一备受瞩目的研究方向。本文介绍了葫芦脲及其衍生物作为超分子纳米反应器/催化剂的研究工作，重点介绍了近年来国际国内在此领域取得的部分研究成果，主要包括葫芦脲通过主客体作用对反应底物的反应活性的影响，希望能给对葫芦脲介入的化学反应感兴趣的研究人员提供参考。

Abstract

Cucurbit[n] urils (CB[n] s), as a kind of rapidly developing supramolecular hosts, have been attracting more and more attentions. With their rigid structures, hydrophobic cavities and electronegative carbonyl groups on the portals, CB[n] s show their unique recognition properties——high selectivity and high binding affinity toward organic cations. In the past decade, CB[n] s have been utilized not only in basic recognition research but also in the construction of complicated three-dimensional materials and even in drug delivery systems. Besides, CB[n] s have been creatively used to control the reaction process and have obtained numerous successes. Herein, this review mainly describes the use of cucurbiturils as supramolecular nanoreactors/catalysts to accelerate or control the reaction process in thermal reactions as well as photoreactions. Moreover, the inhibition effect on guest's activity caused by the encapsulation inside cucurbiturils is also discussed.

Contents
1 Introduction
2 CB[n]s used as supramolecular nanoreactors/catalysts in thermal reactions
2.1 [3+2] cycloaddition reactions
2.2 Solvolysis reactions
2.3 Oxidation reactions
2.4 Other thermal reactions
3 [n]s used as supramolecular nanoreactors/catalysts in photoreactions
3.1 [2+2] cycloaddition reactions
3.2 [4+4] cycloaddition reactions
3.3 Other photoreactions
4 CB[n]s used as inhibiting agents
4.1 Protective agents
4.2 Toxicity inhibitors
4.3 Reaction inhibitors
5 Conclusion

Graphical abstract

关键词

葫芦脲 / 超分子主体 / 纳米反应器 / 催化

Key words

cucurbit[n] urils / supramolecular host / nanoreactors / catalysis

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龚晚君, 赵智勇, 刘思敏*. 葫芦脲作为超分子纳米反应器/催化剂的研究[J]. 化学进展, 2016, 28(12): 1732-1742 DOI:10.7536/PC160936

Gong Wanjun, Zhao Zhiyong, Liu Simin*. Cucurbituril-Based Supramolecular Nanoreactors/Catalysts[J]. Progress in Chemistry, 2016, 28(12): 1732-1742 DOI:10.7536/PC160936

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原文顺序 | 出版日期 | 本文引用

[1] Breslow R. J. Biol. Chem., 2009, 284:1337.
[2] Turro N J. Proc. Natl. Acad. Sci. U.S.A., 2005, 102:10766.
[3] Vriezema D M, Comellas A M, Elemans J A, Cornelissen J J, Rowan A E, Nolte R J. Chem. Rev., 2005, 105:1445.
[4] Davis A V, Yeh R M, Raymond K N. Proc. Natl. Acad. Sci. U.S.A., 2002, 99:4793.
[5] Tabushi I. Acc. Chem. Res., 1982, 15:66.
[6] Breslow R. Acc. Chem. Res., 1995, 28:146.
[7] Garcia H, Ferrer B. Metal Organic Frameworks as Heterogeneous Catalysts. 2013. 365.
[8] Cram D J, Cram J M. Container Molecules and Their Guests. Cambridge:The Royal Society of Chemistry, 1994.
[9] Zarra S, Wood D M, Roberts D A, Nitschke J R. Chem. Soc. Rev., 2015, 44:419.
[10] Yang Z, Ji H. ACS Sustain. Chem. Eng., 2013, 1:1172.
[11] Jiang H, Yang Z, Zhou X, Fang Y, Ji H. Chin. J. Chem. Eng., 2012, 20:784.
[12] Doyagüez E G, Rodríguez-Hernández J, Corrales G, Fernández-Mayoralas A, Gallardo A. Macromolecules, 2012, 45:7676.
[13] Lembo D, Swaminathan S, Donalisio M, Civra A, Pastero L, Aquilano D, Vavia P, Trotta F, Cavalli R. Int. J. Pharm., 2013, 443:262.
[14] Crupi V, Fontana A, Majolino D, Mele A, Melone L, Punta C, Rossi B, Rossi F, Trotta F, Venuti V. J. Inclusion Phenom.Macrocyclic Chem., 2014, 80:69.
[15] Crupi V, Fontana A, Giarola M, Longeville S, Majolino D, Mariotto G, Mele A, Paciaroni A, Rossi B, Trotta F, Venuti V. J. Phys. Chem. B, 2014, 118:624.
[16] Tejashri G, Amrita B, Darshana J. Acta Pharmaceutica, 2013, 63:335.
[17] Kang J, Rebek J. Nature, 1997, 385:50.
[18] Conn M M, Rebek J. Chem. Rev., 1997, 97:1647.
[19] Rebek J. Chem. Soc. Rev., 1996, 25:255.
[20] Yoshizawa M, Tamura M, Fujita M. J. Am. Chem. Soc., 2004, 126:6846.
[21] Pluth M D, Bergman R G, Raymond K N. Science, 2007, 316:85.
[22] Brown C J, Bergman R G, Raymond K N. J. Am. Chem. Soc., 2009, 131:17530.
[23] Wang Z J, Brown C J, Bergman R G, Raymond K N, Toste F D. J. Am. Chem. Soc., 2011, 133:7358.
[24] Wang Z J, Clary K N, Bergman R G, Raymond K N, Toste F D. Nat. Chem., 2013, 5:100.
[25] Kaphan D M, Levin M D, Bergman R G, Raymond K N, Toste F D. Science, 2015, 350:1235.
[26] Freeman W A, Mock W L, Shih N Y. J. Am. Chem. Soc., 1981, 103:2.
[27] Kim J, Jung I S, Kim S Y, Lee E, Kang J K, Sakamoto S, Yamaguchi K, Kim K. J. Am. Chem. Soc., 2000, 122:540.
[28] Liu S, Zavalij P Y, Isaacs L. J. Am. Chem. Soc., 2005, 127:16798.
[29] Cheng X J, Liang L L, Chen K, Ji N N, Xiao X, Zhang J X, Zhang Y Q, Xue S F, Zhu Q J, Ni X L, Tao Z. Angew. Chem. Int. Ed., 2013, 52:7252.
[30] Li Q, Qiu S C, Zhang J, Chen K, Huang Y, Xiao X, Zhang Y, Li F, Zhang Y Q, Xue S F, Zhu Q J, Tao Z, Lindoy L F, Wei G. Org. Lett., 2016, 18:4020.
[31] Cao L, Sekutor M, Zavalij P Y, Mlinaric-Majerski K, Glaser R, Isaacs L. Angew. Chem. Int. Ed., 2014, 53:988.
[32] Han B H, Liu Y. Chin. J. Org. Chem., 2003, 23:139.
[33] Lagona J, Mukhopadhyay P, Chakrabarti S, Isaacs L. Angew. Chem. Int. Ed., 2005, 44:4844.
[34] Isaacs L. Chem. Commun., 2009, 619.
[35] Pemberton B C, Raghunathan R, Volla S, Sivaguru J. Chem.-Eur. J., 2012, 18:12178.
[36] Masson E, Ling X, Joseph R, Kyeremeh-Mensah L, Lu X. RSC Adv., 2012, 2:1213.
[37] Liu Y, Yang H, Wang Z, Zhang X. Chem.-Asian J., 2013, 8:1626.
[38] Ni X L, Xiao X, Cong H, Liang L L, Cheng K, Cheng X J, Ji N N, Zhu Q J, Xue S F, Tao Z. Chem. Soc. Rev., 2013, 42:9480.
[39] Barrow S J, Kasera S, Rowland M J, Del Barrio J, Scherman O A. Chem. Rev., 2015, 115:12320.
[40] Assaf K I, Nau W M. Chem. Soc. Rev., 2015, 44:394.
[41] Liu Y, Yang H, Wang Z, Zhang X. Chem.-Asian J., 2013, 8:1626.
[42] Liu S, Ruspic C, Mukhopadhyay P, Chakrabarti S, Zavalij P Y, Isaacs L. J. Am. Chem. Soc., 2005, 127:15959.
[43] Liu S, Zavalij P Y, Lam Y F, Isaacs L. J. Am. Chem. Soc., 2007, 129:11232.
[44] Liu S, Wu X, Huang Z, Yao J, Liang F, Wu C. J. Inclusion Phenom.Macrocyclic Chem., 2004, 50:203.
[45] Cong H, Tao Z, Xue S F, Zhu Q J. Curr. Org. Chem., 2011, 15:86.
[46] Mock W L, Irra T A, Wepsiec J P, Adhya M. J. Org. Chem., 1989, 54:5302.
[47] Tuncel D, Steinke J H. Chem. Commun., 2002, 496.
[48] Tuncel D, Cindir N, Koldemir U. J. Inclusion Phenom.Macrocyclic Chem., 2006, 55:373.
[49] Tuncel D, Oezsar O, Tiftik H B, Salih B. Chem. Commun., 2007, 1369.
[50] Krasia T C, Steinke J H. Chem. Commun., 2002, 22.
[51] Wang K, Yee C C, Au-Yeung H Y. Chem. Sci., 2016, 7:2787.
[52] Ke C, Smaldone R A, Kikuchi T, Li H, Davis A P, Stoddart J F. Angew. Chem. Int. Ed., 2013, 52:381.
[53] Ke C, Strutt N L, Li H, Hou X, Hartlieb K J, Mcgonigal P R, Ma Z, Iehl J, Stern C L, Cheng C, Zhu Z, Vermeulen N A, Meade T J, Botros Y Y, Stoddart J F. J. Am. Chem. Soc., 2013, 135:17019.
[54] Hou X, Ke C, Cheng C, Song N, Blackburn A K, Sarjeant A A, Botros Y Y, Yang Y W, Stoddart J F. Chem. Commun., 2014, 50:6196.
[55] Finbloom J A, Slack C C, Bruns C J, Jeong K, Wemmer D E, Pines A, Francis M B. Chem. Commun., 2016, 52:3119.
[56] Hou X S, Ke C F, Bruns C J, Mcgonigal P R, Pettman R B, Stoddart J F. Nat. Commun., 2015, 6:9.
[57] Basilio N, Garcia-Rio L, Moreira J A, Pessego M. J. Org. Chem., 2010, 75:848.
[58] Klock C, Dsouza R N, Nau W M. Org. Lett., 2009, 11:2595.
[59] Cong H, Zhao F F, Zhang J X, Zeng X, Tao Z, Xue S F, Zhu Q J. Catal. Commun., 2009, 11:167.
[60] Wang Y H, Cong H, Zhao F F, Xue S F, Tao Z, Zhu Q J, Wei G. Catal. Commun., 2011, 12:1127.
[61] Cong H, Li Z J, Wang Y H, Tao Z, Yamato T, Xue S F, Wei G. J. Mol. Catal. A:Chem., 2013, 374:32.
[62] Cong H, Chen Q, Geng Q, Tao Z, Yamato T. Chin. J. Chem., 2015, 33:545.
[63] Cong H, Yamato T, Tao Z. J. Mol. Catal. A:Chem., 2013, 379:287.
[64] Cong H, Yamato T, Tao Z. New J. Chem., 2013, 37:3778.
[65] Cao M, Lin J, Yang H, Cao R. Chem. Commun., 2010, 46:5088.
[66] Cao M, Wu D, Gao S, Cao R. Chem.-Eur. J., 2012, 18:12978.
[67] Zhao G, Wang Z, Wang R, Li J, Zou D P, Wu Y J. Tetrahedron Lett., 2014, 55:5319.
[68] Reddy K R K K, Cavallini T S, Demets G J F, Silva L F. New J. Chem., 2014, 38:2262.
[69] Bruno S M, Gomes A C, Oliveira T S M, Antunes M M, Lopes A D, Valente A A, Goncalves I S, Pillinger M. Org. Biomol. Chem., 2016, 14:3873.
[70] Zheng L, Sonzini S, Ambarwati M, Rosta E, Scherman O A, Herrmann A. Angew. Chem. Int. Ed., 2015, 54:13007.
[71] Sashuk V, Butkiewicz H, Fialkowski M, Danylyuk O. Chem. Commun., 2016, 52:4191.
[72] Jiao Y, Li W L, Xu J F, Wang G, Li J, Wang Z, Zhang X. Angew. Chem. Int. Ed., 2016, 55:8933.
[73] Jon S Y, Ko Y H, Park S H, Kim H J, Kim K. Chem. Commun., 2001, 1938.
[74] Pattabiraman M, Natarajan A, Kaliappan R, Mague J T, Ramamurthy V. Chem. Commun., 2005, 4542.
[75] Pattabiraman M, Natarajan A, Kaanumalle L S, Ramamurthy V. Org. Lett., 2005, 7:529.
[76] Pattabiraman M, Kaanumalle L S, Natarajan A, Ramamurthy V. Langmuir, 2006, 22:7605.
[77] Maddipatla M V, Kaanumalle L S, Natarajan A, Pattabiraman M, Ramamurthy V. Langmuir, 2007, 23:7545.
[78] Maddipatla M V S N, Pattabiraman M, Natarajan A, Srivastav K, Mague J T, Ramamurthy V. Org. Biomol. Chem., 2012, 10:9219.
[79] Gromov S P, Vedernikov A I, Kuz'mina L G, Kondratuk D V, Sazonov S K, Strelenko Y A, Alfimov M V, Howard J a K. Eur. J. Org. Chem., 2010, 2010:2587.
[80] Barooah N, Pemberton B C, Johnson A C, Sivaguru J. Photochem. Photobiol. Sci., 2008, 7:1473.
[81] Wu X L, Luo L, Lei L, Liao G H, Wu L Z, Tung C H. J. Org. Chem., 2008, 73:491.
[82] Chen B, Cheng S F, Liao G H, Li X W, Zhang L P, Tung C H, Wu L Z. Photochem. Photobiol. Sci., 2011, 10:1441.
[83] Lei L, Luo L, Wu X L, Liao G H, Wu L Z, Tung C H. Tetrahedron Lett., 2008, 49:1502.
[84] Yang H, Ma Z, Wang Z, Zhang X. Polym. Chem., 2014, 5:1471.
[85] Yang H, Liu Y, Liu K, Yang L, Wang Z, Zhang X. Langmuir, 2013, 29:12909.
[86] Yang C, Mori T, Origane Y, Ko Y H, Selvapalam N, Kim K, Inoue Y. J. Am. Chem. Soc., 2008, 130:8574.
[87] Biedermann F, Ross I, Scherman O A. Polym. Chem., 2014, 5:5375.
[88] Wang R, Yuan L, Macartney D H. J. Org. Chem., 2006, 71:1237.
[89] Smitka J, Lemos A, Porel M, Jockusch S, Belderrain T R, Tesarova E, Da-Silva J P. Photochem. Photobiol. Sci., 2014, 13:310.
[90] Saleh N, Koner A L, Nau W M. Angew. Chem. Int. Ed., 2008, 47:5398.
[91] Cong H, Li C R, Xue S F, Tao Z, Zhu Q J, Wei G. Org. Biomol. Chem., 2011, 9:1041.
[92] Ren H, Huang Z, Yang H, Xu H, Zhang X. ChemPhysChem, 2015, 16:523.
[93] Berbeci L S, Wang W, Kaifer A E. Org. Lett., 2008, 10:3721.
[94] Oun R, Floriano R S, Isaacs L, Rowan E G, Wheate N J. Toxicol. Res., 2014, 3:447.
[95] Li S, Chen H, Yang X, Bardelang D, Wyman I W, Wan J, Lee S M Y, Wang R. ACS Med. Chem. Lett., 2015, 6:1174.
[96] Ma D, Zhang B, Hoffmann U, Sundrup M G, Eikermann M, Isaacs L. Angew. Chem. Int. Ed., 2012, 51:11358.
[97] Hoffmann U, Grosse-Sundrup M, Eikermann-Haerter K, Zaremba S, Ayata C, Zhang B, Ma D, Isaacs L, Eikermann M. Anesthesiology, 2013, 119:317.
[98] Miskolczy Z, Megyesi M, Tarkanyi G, Mizsei R, Biczok L. Org. Biomol. Chem., 2011, 9:1061.
[99] Masson E, Shaker Y M, Masson J P, Kordesch M E, Yuwono C. Org. Lett., 2011, 13:3872.
[100] Parente-Carvalho C, Norouzy A, Ribeiro V, Nau W M, Pischel U. Org. Biomol. Chem., 2015, 13:2866.
[101] Yang H, Liu Y, Yang L, Liu K, Wang Z, Zhang X. Chem. Commun., 2013, 49:3905.
[102] 董运红(Dong Y H), 曹利平(Cao L P). 化学进展(Progross in Chemistry), 2016, 28:1039.
[103] Li Q, Qiu S C, Chen K, Zhang Y, Wang R, Huang Y, Tao Z, Zhu Q J, Liu J X. Chem. Commun., 2016, 52:2589.
[104] Liu S, Shukla A D, Gadde S, Wagner B D, Kaifer A E, Isaacs L. Angew. Chem. Int. Ed., 2008, 47:2657.
[105] Gong W, Yang X, Zavali P Y, Isaacs L, Zhao Z, Liu S. Chem.-Eur.J., 2016, 22:17612.