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化学进展 2013, Vol. 25 Issue (06): 869-880 DOI: 10.7536/PC121264 前一篇   后一篇

• Mini Accounts •

苝酰亚胺和大环化合物的超分子组装

蒋邦平, 郭东升, 刘育*   

  1. 南开大学化学系 元素有机化学国家重点实验室 天津 300071
  • 收稿日期:2012-12-28 出版日期:2013-06-25 发布日期:2013-05-02
  • 通讯作者: 刘育 E-mail:yuliu@nankai.edu.cn

Self-Assemblies Based on Perylene Bisimides and Macrocyclic Hosts

Jiang Bangping, Guo Dongsheng, Liu Yu*   

  1. Department of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China
  • Received:2012-12-28 Online:2013-06-25 Published:2013-05-02

苝酰亚胺及其衍生物是一类具有良好的π…π堆积能力和优良的光电性能的n型半导体材料,通过该类化合物与大环化合物构筑纳米超分子组装体是近年来化学、材料科学和纳米科学等领域备受关注的研究之一。本文主要论述了近年来以共价或非共价的方法将超分子大环化合物引入到苝酰亚胺体系构筑出各种纳米功能超分子组装体的研究进展,可以认为超分子大环化合物与苝酰亚胺的组装不仅可以调节苝酰亚胺的光物理行为,而且还可以赋予超分子组装体很多新颖的物理化学特性,使其在传感材料和光电器件等方面展现出很大的潜在应用价值。这些研究极大地拓展了构筑新颖苝酰亚胺纳米超分子组装体的方法。我们相信本文对于进一步构筑具有特定结构和功能的苝酰亚胺大环化合物超分子组装体将起到积极的促进作用。

Perplene bisimides (PBIs) and its derivatives, a rohust class of n-type organic materials, have attracted intense interest because of their intriguing π…π stacking and outstanding optoelectronic properties. The construction of well-defined nanoscopic supramolecular architectures through combining macrocyclic hosts and PBIs is a fascinating topic of interdisciplinary researches on chemistry, materials science, and nanotechnology, which is expected to gain new nano-materials with unique electronic and photonic properties in this mini review, we mainly summarize our recent progresses in directing the formation of the desirable PBI superstructures through introducing macrocyclic hosts into PBI systems by covalent or non-covalent methods. The combination of macrocyclic hosts and PBIs may not only modulate photophysical behaviors of PBIs but also endow corresponding assemblies with novel physicochemical properties, which show a wide range of intriguing applications in sensory materials and optoelectronic devices. Thus, these researches extend the construction of desired functional supramolecular architectures from PBI building blocks, it is hopeful that this review can provide a sophisticated pathway for further designing fascinating PBI-macrocyclic systems.

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[1] Ajayaghosh A, Praveen V K. Acc. Chem. Res., 2007, 40: 644-656

[2] Grimsdale A C, Müllen K. Angew. Chem. Int. Ed., 2005, 44: 5592-5629

[3] Lee C C, Grenier C, Meijer E W, Schenning A P H. J. Chem. Soc. Rev., 2009, 38: 671-683

[4] Ryu J H, Hong D J, Lee M. Chem. Commun., 2008, 1043-1054

[5] Würthner F. Chem. Commun., 2004, 1564-1579

[6] Elemans J A A W, van Hameren R, Nolte R J M, Rowan A E. Adv. Mater., 2006, 18: 1251-1266

[7] Wasielewski M R. J. Org. Chem., 2006, 71: 5051-5066

[8] Zang L, Che Y, Moore J S. Acc. Chem. Res., 2008, 41: 1596-1608

[9] Görl D, Zhang X, Würthner F. Angew. Chem. Int. Ed., 2012, 51: 6328-6348

[10] Ehli C, Oelsner C, MateoAlonso A, Prato M, Schmidt C, Backes C, Hauke F, Hirsch A, Guldi D M. Nat. Chem., 2009, 1: 243-249

[11] Hahn U, Engmann S, Oelsner C, Ehli C, Guldi D M, Torres T. J. Am. Chem. Soc., 2010, 132: 6392-6401

[12] Krieg E, Shirman E, Weissman H, Shimoni E, Wolf S G, Pinkas I, Rybtchinski B. J. Am. Chem. Soc., 2009, 131: 14365-14373

[13] Ryu J H, Jang C J, Yoo Y S, Lim S G, Lee M. J. Org. Chem., 2005, 70: 8956-8962

[14] Osswald P, Leusser D, Stalke D, Würthner F. Angew. Chem. Int. Ed., 2005, 44: 250-253

[15] Langhals H, Jona W, Einsiedl F, Wohnlich S. Adv. Mater., 1998, 10: 1022-1024

[16] Jeon Y M, Lim T H, Kim J G, Kim J S, Gong M S. Bull. Korean Chem. Soc., 2007, 28: 816-820

[17] Slater B J, Davies E S, Argent S P, Nowell H, Lewis W, Blake A J, Champness N R. Chem. Eur. J., 2011, 17: 14746-14751

[18] Jeon Y M, Lim T H, Kim J G, Gong M S. Macromol. Res., 2007, 15: 473-477

[19] Yao H Q, Zhang H Y, Han M, Ding Z J, Zhang Z J, Liu Y. Sci. China, Chem., 2010, 53: 1982-1986

[20] Liu Y, Wang K R, Guo D S, Jiang B P. Adv. Funct. Mater., 2009, 19: 2230-2235

[21] Jiang B P, Guo D S, Liu Y. J. Org. Chem., 2010, 75: 7258-7264

[22] Wang K R, Guo D S, Jiang B P, Sun Z H, Liu Y. J. Phys. Chem. B, 2010, 114: 101-106

[23] Jiang B P, Guo D S, Liu Y. J. Org. Chem., 2011, 76: 6101-6107

[24] Wang K R, Guo D S, Jiang B P, Liu Y. Chem. Commun., 2012, 48: 3644-3646

[25] Takashima Y, Fukui Y, Otsubo M, Hamada N, Yamaguchi H, Yamamoto H, Harada A. Polym J., 2012, 44: 278-285

[26] Zhu G, Zhang X, Gai P, Zhang X, Chen J. Nanoscale, 2012, 4: 5703-5709

[27] Vysotsky M O, Bohmer V, Würthner F, You C C, Rissanen K. Org. Lett., 2002, 4: 2901-2904

[28] Hippius C, Schlosser F, Vysotsky M O, Böhmer V, Würthner F. J. Am. Chem. Soc., 2006, 128: 3870-3871

[29] Hippius C, van Stokkum I H M, Zangrando E, Williams R M, Würthner F. J. Phys. Chem. C, 2007, 111: 13988-13996

[30] Hippius C, van Stokkum I H M, Gsänger M, Groeneveld M M, Williams R M, Würthner F. J. Phys. Chem. C, 2008, 112: 2476-2486

[31] Hippius C, van Stokkum I H M, Zangrando E, Williams R M, Wykes M, Beljonne D, Würthner F. J. Phys. Chem. C, 2008, 112: 14626-14638

[32] Anh N V, Schlosser F, Groeneveld M M, van Stokkum I H M, Würthner F, Williams R M. J. Phys. Chem. C, 2009, 113: 18358-18368

[33] Ernst D, Hildner R, Hippius C, Würthner F, Köhler J. Chem. Phys. Lett., 2009, 482: 93-98

[34] Siekierzycka J R, Hippius C, Würthner F, Williams R M, Brouwer A M. J. Am. Chem. Soc., 2010, 132: 1240-1242

[35] Guo D S, Jiang B P, Wang X, Liu Y. Org. Biomol. Chem., 2012, 10: 720-723

[36] Biedermann F, Elmalem E, Ghosh I, Nau W M, Scherman O A. Angew. Chem. Int. Ed., 2012, 51: 7739-7743

[37] Pedersen C J. J. Am. Chem. Soc., 1967, 89: 7017-7036

[38] Christensen J J, Eatough D J, Izatt R M. Chem. Rev., 1974, 74: 351-384

[39] Bradshaw J S, Izatt R M. Acc. Chem. Res., 1997, 30: 338-345

[40] Gokel G W, Leevy W M, Weber M E. Chem. Rev., 2004, 104: 2723-2750

[41] Krakowiak K E, Bradshaw J S, ZameckaKrakowiak D J. Chem. Rev., 1989, 89: 929-972

[42] An H, Bradshaw J S, Izatt R M, Yan Z. Chem. Rev., 1994, 94: 939-991

[43] Zhang Z J, Zhang H Y, Wang H, Liu Y. Angew. Chem. Int. Ed., 2011, 50: 10834-10838

[44] Liu Y, Chen Y. Acc. Chem. Res., 2006, 39: 681-691

[45] Chen Y, Zhang Y M, Liu Y. Chem. Commun., 2010, 46: 5622-5633

[46] Chen Y, Liu Y. Chem. Soc. Rev., 2010, 39: 495-505

[47] Harada A, Hashidzume A, Yamaguchi H, Takashima Y. Chem. Rev., 2009, 109: 5974-6023

[48] Guo D S, Liu Y. Chem. Soc. Rev., 2012, 41: 5907-5921

[49] Guo D S, Wang K, Liu Y. J. Incl. Phenom. Macrocycl. Chem., 2008, 62: 1-21

[50] Wei A. Chem. Commun., 2006, 1581-1591

[51] Homden D M, Redshaw C. Chem. Rev., 2008, 108: 5086-5130

[52] Lagona J, Mukhopadhyay P, Chakrabarti S, Isaacs L. Angew. Chem. Int. Ed., 2005, 44: 4844-4870

[53] Ko Y H, Kim E, Hwang I, Kim K. Chem. Commun., 2007, 1305-1315

[54] Zheng B, Wang F, Dong S, Huang F. Chem. Soc. Rev., 2012, 41: 1621-1636

[55] Yan X, Wang F, Zheng B, Huang F. Chem. Soc. Rev., 2012, 41: 6042-6065

[56] Huang F, Gibson H W. Progress in Polymer Science, 2005, 30: 982-1018

[57] Che Y, Yang X, Loser S, Zang L. Nano Lett., 2008, 8: 2219-2223

[58] Guo X, Szoka F C. Acc. Chem. Res., 2003, 36: 335-341

[59] Park C, Lee I H, Lee S, Song Y, Rhue M, Kim C. Proc. Natl. Acad. Sci. U.S.A, 2006, 103: 1199-1203

[60] Wang C, Chen Q, Xu H, Wang Z, Zhang X. Adv. Mater., 2010, 22: 2553-2555

[61] Baram J, Shirman E, BenShitrit N, Ustinov A, Weissman H, Pinkas I, Wolf S G, Rybtchinski B. J. Am. Chem. Soc., 2008, 130: 14966-14967

[62] Kelley R F, Shin W S, Rybtchinski B, Sinks L E, Wasielewski M R. J. Am. Chem. Soc., 2007, 129: 3173-3181

[63] Kenis P J A, Noordman O F J, Houbrechts S, van Hummel G J, Harkema S, van Veggel F C J M, Clays K, Engbersen J F J, Persoons A, van Hulst N F, Reinhoudt D N. J. Am. Chem. Soc., 1998, 120: 7875-7883

[64] Schazmann B, Alhashimy N, Diamond D. J. Am. Chem. Soc., 2006, 128: 8607-8614

[65] Gadde S, Batchelor E K, Weiss J P, Ling Y, Kaifer A E. J. Am. Chem. Soc., 2008, 130: 17114-17119

[66] Jiao D, Biedermann F, Tian F, Scherman O A. J. Am. Chem. Soc., 2010, 132: 15734-15743

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