中文   |   English   |   Email Alert

手性组装材料及其在对映体分离中的应用

段小丽, 付雁, 张金利, 李韡*

化学进展 ›› 2013, Vol. 25 ›› Issue (08) :1272-1282

PDF (1240KB)
化学进展 ›› 2013, Vol. 25 ›› Issue (08) :1272-1282 DOI: 10.7536/PC121242
综述与评论
扫码查看或转发全文

手性组装材料及其在对映体分离中的应用

    段小丽, 付雁, 张金利, 李韡*
作者信息 +

Chiral Assembled Materials and Their Application in Enantiomeric Resolution

  • Duan Xiaoli, Fu Yan, Zhang Jinli, Li Wei*
Author information +
文章历史 +

摘要

手性组装材料作为一种新型功能复合材料,已经引起众多科学研究领域的广泛关注,尤其是其在对映体分离方面的潜在应用成为当前的研究热点。本文首先从手性来源角度对手性组装材料的构建机制进行了分类探讨,包括手性诱导、手性放大、手性传递和手性转录4个主要途径,其中具有手性的多孔金属有机骨架、纳米笼是基于手性诱导和手性传递机制构建的组装材料,手性凝胶的形成是基于手性放大机制,而手性转录机制主要用于手性多孔无机材料、螺旋纳米结构的构建。其次,介绍了手性组装材料的对映体识别功能,主要针对金属有机骨架化合物 (MOFs)、手性凝胶和纳米笼三类手性组装材料在对映体分离中的应用进行了综述。阐述了天然生物大分子DNA的手性自组装特性及其对对映体的立体选择性识别功能, 并介绍了DNA螺旋组装结构在手性等离子材料、非对称催化剂设计等方面的应用。最后,归纳了金属有机骨架化合物、手性凝胶、纳米笼和DNA等手性组装材料各自的优势,并对DNA在手性拆分领域的应用前景进行了展望。

Abstract

Chiral assembled materials have received increasing attention in many research areas as new functional composite materials, especially focusing on their potential application in enantiomeric resolution. In this paper, the formation mechanisms of chiral assembled materials are firstly discussed from the origin of chirality, which include four main ways: chiral induction, chiral amplification, chiral transfer and chiral transcription. The formation of chiral porous metal-organic frameworks and nanocages are based on the mechanisms of chiral induction and chiral transfer, while chiral gels are formed on the basis of chiral amplification mechanism. Chiral transcription mechanism is mainly utilized to construct chiral porous inorganic materials and helical nanostructures. Secondly, stereoselective recognition of chiral assembled materials towards optical enantiomers, including metal-organic frameworks (MOFs), chiral gels, nanocages, and their applications on enantioselective separation are reviewed. Thirdly, the chiral self-assembly and stereoselective recognition of natural DNAs, as well as the applications of DNA helical structures in the fields of chiral plasmon materials and asymmetric catalysts are introduced. Finally, the unique advantages of metal-organic frameworks, chiral gels, nanocages and DNA are summerized, and the application prospects of DNAs in chiral separation are outlooked. Contents
1 Introduction
2 Formation mechanisms of chiral assembled materials
2.1 Chiral induction
2.2 Chiral amplification
2.3 Chiral transfer
2.4 Chiral transcription
3 Application of chiral assembled materials in enantioselective recognition
3.1 Metal-organic frameworks(MOFs)
3.2 Chiral gels
3.3 Nanocages
4 Application of natural DNAs in chiral separation
4.1 Chiral assembly
4.2 Enantioseparation
5 Conclusion and outlook

关键词

手性 / 分子组装 / 对映体分离 / DNA

Key words

chirality / molecular assembly / enantiomeric resolution / DNA

引用本文

引用格式 ▾
段小丽, 付雁, 张金利, 李韡. 手性组装材料及其在对映体分离中的应用[J]. 化学进展, 2013, 25(08): 1272-1282 DOI:10.7536/PC121242
Duan Xiaoli, Fu Yan, Zhang Jinli, Li Wei. Chiral Assembled Materials and Their Application in Enantiomeric Resolution[J]. Progress in Chemistry, 2013, 25(08): 1272-1282 DOI:10.7536/PC121242

登录浏览全文

4963

注册一个新账户 忘记密码

参考文献

[1] Pieraccini S, Masiero S, Ferrarini A, Spada G P. Chem. Soc. Rev., 2011, 40(1): 258-271
[2] Strzelecka T E, Davidson M W, Rill R L. Nature, 1988, 331(6155): 457-460
[3] Ma L Q, Falkowski J M, Abney C, Lin W B. Nat. Chem., 2010, 2(10): 838-846
[4] Xu H, Zuend S J, Woll M G, Tao Y, Jacobsen E N. Science, 2010, 327(5968): 986-990
[5] Ito H. Nat. Chem., 2012, 4 (6): 438-439
[6] Phipps R J, Hamilton G L, Toste F D. Nat. Chem., 2012, 4(8): 603-614
[7] Wu X W, Starnes S D. Org. Lett., 2012, 14(14): 3652-3655
[8] Miao W G, Zhang L, Wang X F, Gao H, Jin Q X, Liu M H. Chem. Eur. J., 2013, 19(9): 3209-3036
[9] Lim I S, Mott D, Engelhard M H, Pan Y, Kamodia S, Luo J, Njoki P N, Zhou S Q, Wang L C, Zhong C J. Anal. Chem., 2009, 81(2): 689-698
[10] Xia Y S, Zhou Y L, Tang Z Y. Nanoscale, 2011, 3(4): 1374-1382
[11] Ruiz U, Pagliusi P, Provenzano C, Shibaev V P, Cipparrone G. Adv. Funct. Mater., 2012, 22(14): 2964-2970
[12] Kopp V I, Genack A Z. Nat. Photonics, 2011, 5(8): 470-472
[13] Zhou Y L, Yang M, Sun K, Tang Z Y, Kotov N A. J. Am. Chem. Soc., 2010, 132(17): 6006-6013
[14] Masini F, Kalashnyk N, Knudsen M M, Cramer J R, Lgsgaard E, Besenbacher F, Gothelf K V, Linderoth T R. J. Am. Chem. Soc., 2011, 133(35): 13910-13913
[15] Guo Z, Du Y, Chen Y T, Ng S C, Yang Y H. J. Phys. Chem. C, 2010, 114(34): 14353-14361
[16] Asefa T. Angew. Chem. Int. Ed., 2012, 51(9): 2008-2010
[17] Ishi-i T, Kuwahara R, Takata A, Jeong Y, Sakurai K, Mataka S. Chem. Eur. J., 2006, 12(3): 763-776
[18] Li C H, Chang K C, Tsou C C, Lan Y, Yang H C, Sun S S. J. Org. Chem., 2011, 76(14): 5524-5530
[19] Qiu H B, Inoue Y, Che S A. Angew. Chem. Int. Ed., 2009, 48(17): 3069-3072
[20] Pandeeswar M, Avinash M B, Govindaraju T. Chem. Eur. J., 2012, 18(16): 4818-4822
[21] Wang Y, Li Q. Adv. Mater., 2012, 24(15): 1926-1945
[22] Zhu Z N, Liu W J, Li Z T, Han B, Zhou Y L, Gao Y, Tang Z Y. ACS Nano, 2012, 6(3): 2326-2332
[23] Gibaud T, Barry E, Zakhary M J, Henglin M, Ward A, Yang Y S, Berciu C, Oldenbourg R, Hagan M F, Nicastro D, Meyer R B, Dogic Z. Nature, 2012, 481(7381): 348-353
[24] Chung W J, Oh J W, Kwak K, Lee B Y, Meyer J, Wang E, Hexemer A, Lee S W. Nature, 2011, 478(7369): 364-368
[25] Cai Y G, Bernasek S L. J. Phys. Chem. B, 2005, 109(10): 4514-4519
[26] 袁菁(Yuan J), 张莉(Zhang L), 黄昕(Huang X), 姜思光(Jiang S G), 刘鸣华(Liu M H). 化学进展(Progress in Chemistry), 2005, 17(5): 780-788
[27] Kaiser T E, Stepanenko V, Würthner F. J. Am. Chem. Soc., 2009, 131(19): 6719-6732
[28] Xu H L, Wang W Z. Angew. Chem. Int. Ed., 2007, 46(9): 1489-1492
[29] George S J, Tomovi Dc' Ž, Schenning A P H J, Meijer E W. Chem. Commun., 2011, 47: 3451-3453
[30] Wolffs M, George S J, Tomovi Dc' Ž, Meskers S C J, Schenning A P H J, Meijer E W. Angew. Chem. Int. Ed., 2007,46(43): 8203-8205
[31] Molla M R, Das A, Ghosh S. Chem. Commun., 2011, 47(31): 8934-8936
[32] Morris R E, Bu X H. Nat. Chem., 2010, 2(5): 353-361
[33] Sun C Y, Qin C, Wang C G, Su Z M, Wang S, Wang X L, Yang G S, Shao K Z, Lan Y Q, Wang E B. Adv. Mater., 2011, 23(47): 5629-5632
[34] Lan Y Q, Li S L, Wang X L, Shao K Z, Du D Y, Su Z M, Wang E B. Chem. Eur. J., 2008, 14(32): 9999-10006
[35] Palmans A R A, Meijer E W. Angew. Chem. Int. Ed., 2007, 46(47): 8948-8968
[36] Freire F, Seco J M, Quiñoá E, Riguera R. Angew. Chem. Int. Ed., 2011, 50(49): 11692-11696
[37] Danila I, Pop F, Escudero C, Feldborg L N, Luis J P, Riobe F, Avarvari N, Amabilino D B. Chem. Commun., 2012, 48(38): 4552-4554
[38] Debnath S, Bergamini J F, Artzner F, Mériadec C, Camerel F, Fourmigué M. Chem. Commun., 2012, 48(17): 2283-2285
[39] García F, Sánchez L. J. Am. Chem. Soc., 2012, 134(1): 734-742
[40] Crassous J. Chem. Soc. Rev., 2009, 38(3): 830-845
[41] Yang H, Wang F, Kang Y, Li T H, Zhang J. Chem. Commun., 2012, 48: 9424-9426
[42] Kaczorowski T, Justyniak I, Lipińska T, Lipkowski J, Lewiński J. J. Am. Chem. Soc., 2009, 131(15): 5393-5395
[43] Ho R M, Li M C, Lin S C, Wang H F, Lee Y D, Hasegawa H, Thomas E L. J. Am. Chem. Soc., 2012, 134(26): 10974-10986
[44] Revol J F, Godbout L, Gray D G. J. Pulp Pap. Sci., 1998, 24(5): 146-149
[45] Shopsowitz K E, Qi H, Hamad W Y, MacLachlan M J. Nature, 2010, 468(7322): 422-426
[46] Shopsowitz K E, Hamad W Y, MacLachlan M J. J. Am. Chem. Soc., 2012, 134(2): 867-870
[47] Herault C A, Banu A, Barboiu M, Michau M, Lee A V D. Angew. Chem. Int. Ed., 2007, 46(23): 4268-4272
[48] Li C, Deng K, Tang Z Y, Jiang L. J. Am. Chem. Soc., 2010, 132(23): 8202-8209
[49] Liu B, Han L, Che S A. Angew. Chem. Int. Ed., 2012, 51(4): 923-927
[50] Paik P, Gedanken A, Mastai Y. J. Mater. Chem., 2010, 20(20): 4085-4093
[51] Fireman-Shoresh S, Marx S, Avnir D. Adv. Mater., 2007, 19(16): 2145-2150
[52] Kim B H, Lee S U, Moon D C. Chirality, 2012, 24(12): 1037-1046
[53] Bragg W, Shamsi S A. J. Chromatogr. A, 2012, 1267: 144-155
[54] Pfaunmiller E L, Hartmann M, Dupper C M, Soman S, Hage D S. J. Chromatogr. A, 2012, 1269: 198-207
[55] Dang D B, Wu P Y, He C, Xie Z, Duan C Y. J. Am. Chem. Soc., 2010, 132(41): 14321-14323
[56] Liu Y, Xuan W M, Cui Y. Adv. Mater., 2010, 22(37): 4112-4135
[57] Liu B, Shekhah O, Arslan H K, Liu J X, Woell C, Fischer R A. Angew. Chem. Int. Ed., 2012, 51(3): 807-810
[58] Botas J A, Calleja G, Sanchez-Sanchez M, Orcajo M G. Langmuir, 2010, 26(8): 5300-5303
[59] 贾超(Jia C), 原鲜霞(Yuan X X), 马紫峰(Ma Z F). 化学进展(Progress in Chemistry), 2009, 21(9): 1954-1962
[60] Wu Y N, Li F T, Zhu W, Cui J C, Tao C A, Lin C X, Hannam P M, Li G T. Angew. Chem. Int. Ed., 2011, 50(52): 12518-12522
[61] He J, Yee K K, Xu Z T, Zeller M, Hunter A D, Chui S S Y, Che C M. Chem. Mater., 2011, 23(11): 2940-2947
[62] Ke F, Yuan Y P, Qiu L G, Shen Y H, Xie A J, Zhu J F, Tian X Y, Zhang L D. J. Mater. Chem., 2011, 21(11): 3843-3848
[63] Horcajada P, Serre C, Maurin G, Ramsahye N A, Balas F, Vallet-Regí M, Sebban M, Taulelle F, Férey G. J. Am. Chem. Soc., 2008, 130(21): 6774-6780
[64] Li J R, Tao Y, Yu Q, Bu X H, Sakamoto H, Kitagawa S. Chem. Eur. J., 2008, 14(9): 2771-2776
[65] Jiang J W, Babarao R, Hu Z Q. Chem. Soc. Rev., 2011, 40(7): 3599-3612
[66] Li G, Yu W B, Ni J, Liu T F, Liu Y, Sheng E, Cui Y. Angew. Chem., 2008, 120(7): 1265-1269
[67] Padmanaban M, Müller P, Lieder C, Gedrich K, Grünker R, Bon V, Senkovska I, Baumgärtner S, Opelt S, Paasch S, Brunner E, Glorius F, Klemm E, Kaskel S. Chem. Commun., 2011, 47(44): 12089-12091
[68] Yuan G Z, Zhu C F, Xuan W M, Cui Y. Chem. Eur. J., 2009, 15(26): 6428-6434
[69] Suh K, Yutkin M P, Dybtsev D N, Fedin V P, Kim K. Chem. Commun., 2012, 48(4): 513-515
[70] Wanderley M M, Wang C, Wu C D, Lin W B. J. Am. Chem. Soc., 2012, 134(22): 9050-9053
[71] Li G, Yu W B, Cui Y. J. Am. Chem. Soc., 2008, 130(14): 4582-4583
[72] Wang W J, Dong X L, Nan J P, Jin W Q, Hu Z Q, Chen Y F, Jiang J W. Chem. Commun., 2012, 48(56): 7022-7024
[73] Kosal M E, Chou J H, Wilson S R, Suslick K S. Nat. Mater., 2002, 1(2): 118-121
[74] Das M C, Xiang S C, Zhang Z J, Chen B L. Angew. Chem. Int. Ed., 2011, 50(45): 10510-10520
[75] Das M C, Guo Q S, He Y B, Kim J, Zhao C G, Hong K L, Xiang S C, Zhang Z J, Thomas K M, Krishna R, Chen B L. J. Am. Chem. Soc., 2012, 134(20): 8703-8710
[76] Hirst A R, Smith D K. Chem. Eur. J., 2005, 11(19): 5496-5508
[77] Yang Z M, Liang G L, Xu B. Acc. Chem. Res., 2008, 41(2): 315-326
[78] Ajayaghosh A, Praveen V K, Vijayakumar C. Chem. Soc. Rev., 2008, 37(1): 109-122
[79] George M, Weiss R G. Acc. Chem. Res., 2006, 39(8): 489-497
[80] Li Y G, Wang T Y, Liu M H. Soft Matter, 2007, 3(10): 1312-1317
[81] Sangeetha N M, Maitra U. Chem. Soc. Rev., 2005, 34(10): 821-836
[82] 孔丽(Kong L), 孙涛(Sun T), 张峰(Zhang F),辛飞飞(Xin F F),郝爱友(Hao A Y). 化学进展(Progress in Chemistry), 2012, 24(5): 790-800
[83] Fu X J, Yang Y, Wang N X, Wang H, Yang Y J. J. Mol. Recognit., 2007, 20(4): 238-244
[84] Fages F. Angew. Chem. Int. Ed., 2006, 45(11): 1680-1682
[85] Jintoku H, Takafuji M, Oda R, Ihara H. Chem. Commun., 2012, 48(40): 4881-4883
[86] Jin Q X, Zhang L, Zhu X F, Duan P F, Liu M H. Chem. Eur. J., 2012, 18(16): 4916-4922
[87] Smith D K. Chem. Soc. Rev., 2009, 38(3): 684-694
[88] Jonkheijm P, van der Schoot P, Schenning A P H J, Meijer E W. Science, 2006, 313(5783): 80-83
[89] Naota T, Koori H. J. Am. Chem. Soc., 2005, 127(26): 9324-9325
[90] Chen X, Huang Z, Chen S Y, Li K, Yu X Q, Pu L. J. Am. Chem. Soc., 2010, 132(21): 7297-7299
[91] Tu T, Fang W W, Bao X L, Li X B, Dtz K H. Angew. Chem. Int. Ed., 2011, 50(29): 6601-6605
[92] Liu T F, Liu Y, Xuan W M, Cui Y. Angew. Chem. Int. Ed., 2010, 49(24): 4121-4124
[93] Xuan W M, Zhang M N, Liu Y, Chen Z J, Cui Y. J. Am. Chem. Soc., 2012, 134(16): 6904-6907
[94] Bren U, Lah J, Bren M, Martinek V, Florian J. J. Phys. Chem. B, 2010, 114(8): 2876-2885
[95] Arcella A, Portella G, Ruiz M L, Eritja R, Vilaseca M, Gabelica V, Orozco M. J. Am. Chem. Soc., 2012, 134(15): 6596-6606
[96] Lech C J, Li Z, Heddi B, Phan A T. Chem. Commun., 2012, 48(93): 11425-11427
[97] Choi J, Kim S, Tachikawa T, Fujitsuka M, Majima T. J. Am. Chem. Soc., 2011, 133(40): 16146-16153
[98] Saha S, Chakraborty K, Krishnan Y. Chem. Commun., 2012, 48(19): 2513-2515
[99] Campolongo M J, Kahn J S, Cheng W L, Yang D Y, Campolongo T G, Luo D. J. Mater. Chem., 2011, 21(17): 6113-6121
[100] Pinheiro A V, Han D R, Shih W M, Yan H. Nat. Nanotechnol., 2011, 6(12):763-772
[101] Howson S E, Bolhuis A, Brabec V, Clarkson G J, Malina J, Rodger A, Scott P. Nat. Chem., 2012, 4(1): 31-36
[102] 陈晓东(Chen X D), 姜思光(Jiang S G), 刘鸣华(Liu M H). 化学进展(Progress in Chemistry), 2003, 15(5): 367-373
[103] Mitchell J C, Harris J R, Malo J, Bath J, Turberfield A J. J. Am. Chem. Soc., 2004, 126(50): 16342-16343
[104] Goodman R P, Schaap I A T, Tardin C F, Erben C M, Berry R M, Schmidt C F, Turberfield A J. Science, 2005, 310(5754): 1661-1665
[105] Zhang C, Wu W M, Li X, Tian C, Qian H, Wang G S, Jiang W, Mao C D. Angew. Chem. Int. Ed., 2012, 51(32): 7999-8002
[106] Qi H, Shopsowitz K E, Hamad W Y, MacLachlan M J. J. Am. Chem. Soc., 2011, 133(11): 3728-3731
[107] Douglas S M, Dietz H, Liedl T, Hogberg B, Graf F, Shih W M. Nature, 2009, 459(7250): 414-418
[108] Kuzyk A, Schreiber R, Fan Z Y, Pardatscher G, Roller E M, Hgele A, Simmel F C, Govorov A O, Liedl T. Nature, 2012, 483(7389): 311-314
[109] Li Z T, Zhu Z N, Liu W J, Zhou Y L, Han B, Gao Y, Tang Z Y. J. Am. Chem. Soc., 2012, 134(7): 3322-3325
[110] Aldaye F A, Palmer A L, Sleiman H F. Science, 2008, 321(5897): 1795-1799
[111] Tanaka K, Clever G H, Takezawa Y, Yamada Y, Kaul C, Shionoya M, Carell T. Nat. Nanotechnol., 2006, 1(3): 190-194
[112] Condon A. Nat. Rev. Genet., 2006, 7(7): 565-575
[113] Clever G H, Kaul C, Carell T. Angew. Chem. Int. Ed., 2007, 46(33): 6226-6236
[114] Qu X G, Trent J O, Fokt I, Priebe W, Chaires J B. PNAS, 2000, 97(22): 12032-12037
[115] Shoji A, Kuwahara M, Ozaki H, Sawai H. J. Am. Chem. Soc., 2007, 129(5): 1456-1464
[116] Yu H J, Wang X H, Fu M L, Ren J S, Qu X G. Nucleic Acids Res., 2008, 36(17): 5695-5703
[117] Zhao C Q, Geng J, Feng L Y, Ren J S, Qu X G. Chem. Eur. J., 2011, 17(29): 8209-8215
[118] Michaud M, Jourdan E, Villet A, Ravel A, Grosset C, Peyrin E. J. Am. Chem. Soc., 2003, 125(28): 8672-8679
[119] Michaud M, Jourdan E, Ravelet C, Villet A, Ravel A, Grosset C, Peyrin E. Anal. Chem., 2004, 76(4): 1015-1020
[120] Ravelet C, Boulkedid R, Ravel A, Grosset C, Villet A, Fize J, Reyrin E. J. Chromatogr. A, 2005, 1076: 62-70
[121] Zhao C Q, Ren J S, Gregoliński J, Lisowski J, Qu X G. Nucleic Acids Res., 2012, 40(16): 8186-8196
[122] Feng L Y, Zhao C Q, Xiao Y, Wu L, Ren J S, Qu X G. Chem. Commun., 2012, 48(55): 6900-6902
[123] Feng L Y, Xu B L, Ren J S, Zhao C Q, Qu X G. Chem. Commun., 2012, 48(72): 9068-9070
[124] Roelfes G, Boersma A J, Feringa B L. Chem. Commun., 2006, (6): 635-637
[125] Coquière D, Feringa B L, Roelfes G. Angew. Chem. Int. Ed., 2007, 46(48): 9308-9311
[126] Boersma A J, Feringa B L, Roelfes G. Angew. Chem. Int. Ed., 2009, 121(18): 3396-3398
[127] Tang Z, Goncalves D P N, Wieland M, Marx A, Hartig J S. ChemBioChem, 2008, 9(7): 1061-1064
[128] Boersma A J, Coquière D, Geerdink D, Rosati F, Feringa B L, Roelfes G. Nat. Chem., 2010, 2(11):991-995
[129] Wang C H, Jia G Q, Zhou J, Li Y H, Liu Y, Lu S M, Li C. Angew. Chem. Int. Ed., 2012, 51(37): 9352-9355
[130] Gu Z Y, Yang C X, Chang N, Yan X P. Acc. Chem. Res., 2012, 45(5): 734-745
PDF (1240KB)

5723

访问

0

被引

详细

导航
相关文章

/

〈 〉