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化学进展  2014 

三重和四重氢键体系:设计、结构和应用

DOI: 10.7536/PC131051, PP. 706-726

Keywords: 氢键,三重氢键体系,四重氢键体系,超分子聚合物,超分子化学

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Abstract:

氢键是超分子化学领域具有特别重要地位的一种非共价作用。近年来,通过氢键自组装制备超分子聚合物已经成为超分子化学的一个热门研究领域。构筑性能优良的多重氢键体系奠定了这个领域的研究基础。其中,三重和四重氢键体系在构筑超分子组装体方面得到了广泛应用。本文综述了三重氢键、四重氢键组装体系的研究进展及其应用,重点介绍了各种三重氢键、四重氢键体系的设计思路和影响其稳定性的各种因素。

References

[1]  Steed J W, Atwood J L. Supramolecular Chemistry. 2nd ed. NY: John Wiley-Sons Ltd., 2008.
[2]  Pranata J, Wierschke S G, Jorgensen W L. J. Am. Chem. Soc., 1991, 113: 2810.
[3]  Murray T J, Zimmerman S C. J. Am. Chem. Soc., 1992, 114: 4010.
[4]  Sijbesma R P, Meijer E W. Chem. Commun., 2003, 5.
[5]  Zimmerman S C, Corbin P S. in Structure and Bonding (Berlin), 2000, 96: 63.
[6]  黄飞鹤(Huang F H), 翟春熙(Zhai C X), 郑波(Zheng B), 李世军(Li S J). 超分子聚合物(Supramolecular Polymers). 杭州: 浙江大学出版社(Hangzhou: Zhejiang University Press), 2012.
[7]  Zheng B, Wang F, Dong S, Huang F. Chem. Soc. Rev., 2012, 41: 1621.
[8]  Aida T, Meijer E W, Stupp S I. Science, 2012, 335: 813.
[9]  Hamilton A D, van Engen D. J. Am. Chem. Soc., 1987, 109: 5035.
[10]  Beijer F H, Sijbesma R P, Vekemans J A J M, Meijer E W, Kooijman H, Spek A L. J. Org. Chem., 1996, 61: 6371.
[11]  Fouquey C, Lehn J M, Levelut A M. Adv. Mater., 1990, 2: 254.
[12]  Lehn J M. Makromol. Chem. Macromol. Symp., 1993, 69: 1.
[13]  Gulik-Krzywicki T, Fouquey C, Lehn J M. Proc. Natl. Acad. Sci. U. S. A., 1993, 90: 163.
[14]  Kotera M, Lehn J M, Vigneron J P. J. Chem. Soc. Chem. Commun., 1994, 2: 197.
[15]  Kotera M, Lehn J M, Vigneron J P. Tetrahedron, 1995, 51: 1953.
[16]  Chang S K, Hamilton A D. J. Am. Chem. Soc., 1988, 110: 1318.
[17]  Chang S K, Ungen D V, Hamilton A D. J. Am. Chem. Soc., 1991, 113: 7640.
[18]  Kelly T R, Zhao C, Bridger G J. J. Am. Chem. Soc., 1989, 111: 3744.
[19]  McGhee A M, Kilner C, Wilson A J. Chem. Commun., 2008, 344.
[20]  Bell D A, Anslyn E V. Tetrahedron Lett., 1995, 51: 7161.
[21]  Wang H B, Mudraboyina B P, Li J X, Wisner J A. Chem. Commun., 2010, 46: 7343.
[22]  Ducharme Y, Wuest J D. J. Org. Chem., 1988, 53: 5787.
[23]  Wash P L, Maverick E, Chiefari J, Lightner D A. J. Am. Chem. Soc., 1997, 119: 3802.
[24]  Griffin R J, Lowe P R. J. Chem. Soc. Perkin Trans. 1, 1992: 1811.
[25]  Beijer F H, Kooijman H, Spek A L, Sijbesma R P, Meijer E W. Angew. Chem. Int. Ed., 1998, 37: 75.
[26]  Hirschberg J H K K, Brunsveld L, Ramzi A, Vekemans J A J M, Sijbesma R P, Meijer E W. Nature, 2000, 407: 167.
[27]  Brunsveld L, Vekemans J A J M, Hirschberg J H K K, Sijbesma R P, Meijer E W. Proc. Natl. Acad. Sci. U. S. A., 2002, 99: 4977.
[28]  Li J, Wisner J A, Jennings M C. Org. Lett., 2007, 9: 3267.
[29]  Li J, Pandelieva A T, Rowley C N, Woo T K, Wisner J A. Org. Lett., 2012, 14: 5772.
[30]  Taylor A, Berryman V E J, Boyd R J. J. Phys. Chem. A, 2012, 116: 7965.
[31]  Sijbesma R P, Beijer F H, Brunsveld L, Folmer B J B, Hirschberg J H K K, Meijer E W. Science, 1997, 278: 1601.
[32]  Beijer F H, Sijbesma R P, Kooijman H, Spek A L, Meijer E W. J. Am. Chem. Soc., 1998, 120: 6761.
[33]  Keizer H M, Sijbesma R P, Meijer E W. Eur. J. Org., 2004, 12: 2553.
[34]  Soentjens S H M, Sijbesma R P, van Genderen M H P, Meijer E W. J. Am. Chem. Soc., 2000, 122: 7487.
[35]  Sánchez L, Rispens M T, Hummelen J C. Angew. Chem. Int. Ed., 2002, 41: 838.
[36]  Xu J F, Chen Y Z, Wu D Y, Wu L Z, Tung C H, Yang Q Z. Angew. Chem. Int. Ed., 2013, 52: 9738.
[37]  Yan X, Li S, Pollock J B, Cook T R, Chen J, Zhang Y, Ji X, Yu Y, Huang F, Stang P J. Proc. Natl. Acad. Sci. U. S. A., 2013, 110: 15585.
[38]  Corbin P S, Zimmerman S C. J. Am. Chem. Soc., 1998, 120: 9710.
[39]  Corbin P S, Lawless L J, Li Z T, Ma Y G, Witmer M J, Zimmerman S C. Proc. Natl. Acad. Sci. U. S. A., 2002, 99: 5099.
[40]  Baruah P K, Gonnade R, Phalgune U D, Sanjayan G J. J. Org. Chem., 2005, 70: 6461.
[41]  Sun H, Steeb J, Kaifer A E. J. Am. Chem. Soc., 2006, 128: 2820.
[42]  Cui L, Gadde S, Shukla A D, Sun H, Mague J T, Kaifer A E. Chem. Commun., 2008, 1446.
[43]  Corbin P S, Zimmerman S C, Thiessen P A, Hawryluk N A, Murray T J. J. Am. Chem. Soc., 2001, 123: 10475.
[44]  Chien C H, Leung M M, Su J K, Li G H, Liu Y H, Wang Y. J. Org. Chem., 2004, 69: 1866.
[45]  Hisamatsu Y, Shirai N, Ikeda S I, Odashima K. Org. Lett., 2009, 11: 4342.
[46]  Prabhakaran P, Puranik V G, Sanjayan G J. J. Org. Chem., 2005, 70: 10067.
[47]  Mudraboyina B P, Wisner J A. Chem. Eur. J., 2012, 18: 14157.
[48]  Ligthart G B W L, Ohkawa H, Sijbesma R P, Meijer E W. J. Org. Chem., 2006, 71: 375.
[49]  Anderson C A, Taylor P G, Zeller M A, Zimmerman S C. J. Org. Chem., 2010, 75: 4848
[50]  Park T, Zimmerman S C, Nakashima S. J. Am. Chem. Soc., 2005, 127: 6520.
[51]  Park T, Todd E M, Nakashima S, Zimmerman S C. J. Am. Chem. Soc., 2005, 127: 18133.
[52]  Ong H C, Zimmerman S C. Org. Lett., 2006, 8: 1589.
[53]  Kuykendall D W, Anderson C A, Zimmerman S C. Org. Lett., 2009, 11: 61.
[54]  Park T, Zimmerman S C. J. Am. Chem. Soc., 2006, 128: 11582.
[55]  Park T, Zimmerman S C. J. Am. Chem. Soc., 2006, 128: 13986.
[56]  Quinn J R, Zimmerman S C. Org. Lett., 2004, 6: 1649.
[57]  Hisamatsu Y, Shirai N, Ikeda S I. Odashima K. Org. Lett., 2010, 12: 1776.
[58]  Pellizzaro M L, Barrett S A, Fisher J, Wilson A J. Org. Biomol. Chem., 2012, 10: 4899.
[59]  Yang Y, Yang Z Y, Yi Y P, Xiang J F, Chen C F, Wan L J, Shuai Z G. J. Org. Chem., 2007, 72: 4936.
[60]  Taubitz J, Lüning U. Aust. J. Chem., 2009, 62: 1550.
[61]  Blight B A, Hunter C A, Leigh D A, McNab H, Thomson P I T. Nat. Chem., 2011, 3: 244.
[62]  Wilson A. Nat. Chem., 2011, 3: 193.
[63]  Leigh D A, Robertson C C, Slawin A M Z, Thomson P I T. J. Am. Chem. Soc., 2013, 135: 9939.
[64]  Gong B, Yan Y F, Zeng H Q, Skrzypczak-Jankunn E, Kim Y W, Zhu J, Ickes H. J. Am. Chem. Soc., 1999, 121: 5607.
[65]  Yang X W, Martinovic S, Smith R D, Gong B. J. Am. Chem. Soc., 2003, 125: 9932.
[66]  Yang X, Gong B. Angew. Chem. Int. Ed., 2005, 44: 1352.
[67]  Davis A P, Draper S M, Dunne G, Ashton P. Chem. Comm., 1999, 2265.
[68]  Schmuck C, Wienand W. J. Am. Chem. Soc., 2003, 125: 452.P, Hailes H C. J. Am. Chem. Soc., 2006, 128: 6544-6545.
[69]  Corbin P S, Zimmerman S C. J. Am. Chem. Soc., 2000, 122: 3779-3780
[70]  Chien C-H, Leung M-k, Su J-K, Li G-H, Liu Y-H, Wang Y. J. Org. Chem., 2004, 69: 1866-1871
[71]  Hisamatsu Y, Shirai N, Ikeda S I, Odashima K. Org. Lett., 2009, 11: 4342-4345
[72]  Prabhakaran P, Puranik V G, Sanjayan G J. J. Org. Chem., 2005, 70: 10067-10072
[73]  Park T, Zimmerman S C, Nakashima S. J. Am. Chem. Soc., 2005, 127: 6520-6521
[74]  Park T, Todd E M, Nakashima S, Zimmerman S C. J. Am. Chem. Soc., 2005, 127: 18133-18142
[75]  Park T, Zimmerman S C. J. Am. Chem. Soc., 2006, 128: 14236-14237
[76]  Anderson C A, Jones A R, Briggs E M, Novitsky E J, Kuykendall D W, Sottos N R., Zimmerman S C. J. Am. Chem. Soc., 2013, 135: 7288-7295
[77]  Zhang Y, Anderson C A, Zimmerman S C. Org. Lett., 2013, 15: 3506-3509
[78]  Taubitz J, Lüning U, Grotemeyer J. Chem. Commun., 2004,21: 2400–2401
[79]  Quinn J R, Zimmerman S C. Org. Lett., 2004, 6: 1649-1652
[80]  Hisamatsu Y, Shirai N, Ikeda S I. Odashima K. Org. Lett., 2010, 12: 1776-1779
[81]  Pellizzaro M L, Barrett S A, Fisher J, Wilson A J. Org. Biomol. Chem., 2012, 10: 4899-4906
[82]  Zhao X, Wang X Z, Jiang X-K, Chen Y-Q, Li Z T, Chen G-Ju. J. Am. Chem. Soc., 2003, 125: 15128-15139
[83]  Zhou Y X, Zhao X, Li Z T, Chen G-J, Liu R-Z. Acta Chim. Sin., 2003, 61: 963-969
[84]  Leigh D A, Robertson C C, Slawin A M Z, Thomson P I T. J. Am. Chem. Soc., 2013, 135: 9939-9943
[85]  Gong B, Yan Y F, Zeng H Q, Skrzypczak-Jankunn E, Kim, Y W, Zhu J, Ickes H. J. Am. Chem. Soc., 1999, 121: 5607-5608
[86]  Yang X, Gong B. Angew. Chem., Int. Ed., 2005, 44: 1352-1356
[87]  Roland J T, Guan Z. J. Am. Chem. Soc., 2004, 126: 14328-14329
[88]  Zhang P, Chu H-Z, Li X-H, Feng W, Deng P-C,Yuan L, Gong B. Org. Lett., 2011, 13: 54-57
[89]  Davis A P, Draper S M, Dunne G, Ashton P. Chem. Comm., 1999, 22: 2265-2266
[90]  Schmuck C, Wienand W. J. Am. Chem. Soc., 2003, 125: 452-459 ?
[91]  Prins L J, Reinhoudt D N, Timmerman P. Angew. Chem. Int. Ed., 2001, 40: 2382.
[92]  Jorgensen W L, Pranata J. J. Am. Chem. Soc., 1990, 112: 2008.
[93]  Zimmerman S C, Murray T J. Tetrahedron Lett., 1994, 35: 4077.
[94]  Sartorius J, Schneider H J. Chem. Eur. J., 1996, 2: 1446.
[95]  Yan X, Wang F, Zheng B, Huang F. Chem. Soc. Rev., 2012, 41: 6042.
[96]  De Greef T F A, Meijer E W. Nature, 2008, 453: 171.
[97]  De Greef T F A, Smulders M M J, Wolffs M, Schenning A P H J, Sijbesma R P, Meijer E W. Chem. Rev., 2009, 109: 5687.
[98]  Yang S K, Zimmerman S C. Isr. J. Chem., 2013, 53: 511.
[99]  Feibush B, Figueroa A, Charles R, Onan K D, Feibush P, Karger B L. J. Am. Chem. Soc., 1986, 108: 3310.
[100]  Kyogoku Y, Lord R C, Rich A. Proc. Natl. Acad. Sci. U. S. A., 1967, 57: 250.
[101]  Park T K, Schroeder J, Rebek J. J. Am. Chem. Soc., 1991, 113: 5125.
[102]  Kelly T R, Bridger G J, Zhao C. J. Am. Chem. Soc., 1990, 112: 8024.
[103]  Hisamatsu Y, Fukumi Y, Shirai N, Ikeda S I, Odashima K. Tetrahedron Lett., 2008, 49: 2005.
[104]  Gooch A, McGhee A M, Pellizzaro M L, Lindsay C I, Wilson A J. Org. Lett., 2011, 13: 240.
[105]  Gooch A, Barrett S, Fisher J, Lindsay C I, Wilson A J. Org. Biomol. Chem., 2011, 9: 5938.
[106]  Murray T J, Zimmerman S C, Kolotuchin S V. Tetrahedron Lett., 1995, 51: 635.
[107]  Djurdjevic S, Leigh D A, McNab H, Parsons S, Teobaldi G, Zerbetto F. J. Am. Chem. Soc., 2007, 129: 476.
[108]  Blight B A, Camara-Campos A, Djurdjevic S, Kaller M, Leigh D A, McMillan F M, McNab H, Slawin A M Z. J. Am. Chem. Soc., 2009, 131: 14116.
[109]  Wang H B, Mudraboyina B P, Wisner J A. Chem. Eur. J., 2012, 18: 1322.
[110]  齐志奇(Qi Z Q), 邵学斌(Shao X B), 赵新(Zhao X), 李晓强(Li X Q), 王晓钟(Wang X Z), 张未星(Zhang W X), 蒋锡夔(Jiang X K), 黎占亭(Li Z T). 有机化学(Organic Chemistry), 2003, 5: 403.
[111]  Yang Y, Yan H J, Chen C F, Wan L J. Org. Lett., 2007, 9: 4991.
[112]  Martin A M, Butler R S, Ghiviriga I, Giessert R E, Abboud K A, Castellano R K. Chem. Commun, 2006, 42: 4413.
[113]  Ikegami M, Arai T. Chem. Lett., 2001, 7: 694.
[114]  Ohshiro I, Ikegami M, Nishimura Y, Arai T. Bull. Chem. Soc. Jpn., 2006, 79: 1950.
[115]  Guo D, Sijbesma R P, Zuilhof H. Org. Lett., 2004, 6: 3667.
[116]  Wang X Z, Li X Q, Shao X B, Zhao X, Deng P, Jiang X K, Li Z T, Chen Y Q. Chem. Eur. J., 2003, 9: 2904.
[117]  Ligthart G B W L, Ohkawa H, Sijbesma R P, Meijer E W. J. Am. Chem. Soc., 2005, 127: 810.
[118]  Wang S, Wu L, Zhang L, Tung C. Chin. Sci. Bull., 2006, 51: 129.
[119]  Sánchez L, Martín N, Guldi D M. Angew. Chem. Int. Ed., 2005, 44: 5374.
[120]  Rispens M T, Sanchez L, Knol J, Hummelen J C. Chem. Commun., 2001, 2: 161.
[121]  Gonzalez J J, Gonzalez S, de Mendoza J, Priego E M, Martin N, Luo C P, Guldi D M. Chem. Commun., 2001, 163.
[122]  Yan X, Jiang B, Cook T R, Zhang Y, Li J, Yu Y, Huang F, Yang H B, Stang P J. J. Am. Chem. Soc., 2013, 135: 16813.
[123]  Lafitte V G H, Aliev A E, Horton P N, Hursthouse M B, Bala K, Golding P, Hailes H C. J. Am. Chem. Soc., 2006, 128: 6544.
[124]  Corbin P S, Zimmerman S C. J. Am. Chem. Soc., 2000, 122: 3779.
[125]  Park T, Zimmerman S C. J. Am. Chem. Soc., 2006, 128: 14236.
[126]  Anderson C A, Jones A R, Briggs E M, Novitsky E J, Kuykendall D W, Sottos N R, Zimmerman S C. J. Am. Chem. Soc., 2013, 135: 7288.
[127]  Zhang Y, Anderson C A, Zimmerman S C. Org. Lett., 2013, 15: 3506.
[128]  Li Y, Park T, Quansah J K, Zimmerman S C. J. Am. Chem. Soc., 2011, 133: 17118.
[129]  Lüning U, Kühl C. Tetrahedron Lett., 1998, 39: 5735.
[130]  Brammer S, Lüning U, Kühl C. Eur. J. Org. Chem., 2002, 23: 4054.
[131]  Lüning U, Kühl C, Uphoff A. Eur. J. Org. Chem., 2002, 23: 4063.
[132]  Taubitz J, Lüning U, Grotemeyer J. Chem. Commun., 2004, 2400.
[133]  Zhao X, Wang X Z, Jiang X K, Chen Y Q, Li Z T, Chen G J. J. Am. Chem. Soc., 2003, 125: 15128.
[134]  Zhou Y X, Zhao X, Li Z T, Chen G J, Liu R Z. Acta Chim. Sin., 2003, 61: 963.
[135]  Feng D J, Wang P, Li X Q, Li Z T. Chin. J. Chem., 2006, 24: 1200.
[136]  Roland J T, Guan Z. J. Am. Chem. Soc., 2004, 126: 14328.
[137]  Zhang P, Chu H Z, Li X H, Feng W, Deng P C, Yuan L, Gong B. Org. Lett., 2011, 13: 54.
[138]  Corbin P S, Zimmerman S C, Thiessen P A, Hawryluk N A, Murray T J. J. Am. Chem. Soc., 2001, 123: 10475-10488
[139]  Mudraboyina B P, Wisner J A. Chem. Eur. J., 2012, 18: 14157-14164
[140]  Ligthart G B W L, Ohkawa H, Sijbesma R P, Meijer E W. J. Org. Chem., 2006, 71: 375-378
[141]  Anderson C A, Taylor P G, Zeller M A, Zimmerman S C. J. Org. Chem., 2010, 75: 4848-4851
[142]  Ong H C, Zimmerman S C. Org. Lett., 2006, 8: 1589-1592
[143]  Kuykendall D W, Anderson C A, Zimmerman S C. Org. Lett., 2009, 11: 61-64
[144]  Park T, Zimmerman S C. J. Am. Chem. Soc., 2006, 128: 11582-11590
[145]  Park T, Zimmerman S C. J. Am. Chem. Soc., 2006, 128: 13986-13987
[146]  Li Y, Park T, Quansah J K, Zimmerman S C. J. Am. Chem. Soc., 2011, 133: 17118-17121
[147]  Lüning U, Kühl C. Tetrahedron Lett., 1998, 39: 5735-5738
[148]  Brammer S, Lüning U, Kühl C. Eur. J. Org. Chem., 2002, 23: 4054-4062
[149]  Lüning U, Kühl C, Uphoff A. Eur. J. Org. Chem., 2002, 23: 4063-4070
[150]  Feng D-J, Wang P, Li X-Q, Li Z T. Chin. J. Chem., 2006, 24: 1200-1208
[151]  Yang Y, Yang Z-Y, Yi Y-P, Xiang J-F, Chen C-F, Wan L-J, Shuai Z-G. J. Org. Chem., 2007, 72: 4936-4946
[152]  Taubitz J, Lüning U. Aust. J. Chem., 2009, 62: 1550-1555
[153]  Blight B A, Hunter C A, Leigh D A, McNab H, Thomson P I T. Nature Chem., 2011, 3: 244-248
[154]  Wilson A. Nature Chem., 2011, 3: 193-194
[155]  Yang X W, Martinovic S, Smith R D, Gong B. J. Am. Chem. Soc., 2003, 125: 9932-9933

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