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Progress in Chemistry 2013, Vol. 25 Issue (07): 1079-1089 DOI: 10.7536/PC130116 Previous Articles   Next Articles

• Review •

9,10-Distyrylanthracene Derivatives: Aggregation Induced Emission, Mechanism and Their Applications

Xu Bin, Zhang Jibo, Ma Suqian, Chen Jinlong, Dong Yujie, Tian Wenjing*   

  1. State Key Laboratory of Supramolecular Structure and Materials, Jilin University, Changchun 130012, China
  • Received: Revised: Online: Published:
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Comparing the conventional luminescent molecules, whose fluorescence is quenched once they aggregate, molecules with aggregation-induced emission properties exhibit significantly enhanced emission in solid state or aggregates due to their unique molecular structures and stacking modes, showing potential applications in optoelectronic devices, biochemical sensors and bioimaging. This paper mainly focus on the AIE properties of 9,10-distyrylanthracene (DSA) derivatives, and the AIE mechanism such as the restriction of intramolecular rotation, the twisted conformation of molecules and the packing structures. Also, the applications of DSA derivatives in solid state emitters, stimuli-responsive materials, biochemical sensors and bioimaging are introduced. Contents
1 Introduction
2 AIE molecules based on 9,10-distyrylanthracene
2.1 Small molecules
2.2 Macromolecules
3 The AIE mechanism of 9,10-distyrylanthracene based molecules
4 Applications of AIE luminogens based on 9,10-distyrylanthracene derivatives
4.1 High efficiency solid emitter
4.2 Piezallochromy
4.3 Fluorescent sensor
4.4 Bioimaging
5 Conclusion and outlook

Key words: distyrylanthracene, aggregation-induced emission, high efficiency solid state emitters

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[1] Birks J B. Photophysics of Aromatic Molecules, Wiley, 1970
[2] Jenekhe S A, Osaheni J A. Science, 1994, 265: 765-768
[3] Friend R H, Gymer R W, Holmes A B, Burroughes J H, Marks R N, Taliani C, Bradley D D C, Dos Santos D A, Bredas J L, Logdlund M, Salaneck W R. Nature, 1999, 397: 121-128
[4] 钱立军(Qian L J), 支俊格(Zhi J G), 佟斌(Tong B), 杨帆(Yang F), 赵玮(Zhao W), 董宇平(Dong Y P). 化学进展(Progress in Chemistry), 2008, 20(5): 673-678
[5] 张双(Zhang S), 秦安军(Qin A J), 孙景志(Sun J Z), 唐本忠(Tang B Z). 化学进展(Progress in Chemistry), 2011, 23(4): 623-636
[6] Borisov S M, Wolfbeis O S. Chem. Rev., 2008, 108: 423-461
[7] Chen L, Xu S, McBranch D, Whitten D. J. Am. Chem. Soc., 2000, 122: 9302-9303
[8] Taylor P N, O’Connell M J, McNeill L A, Hall M J, Aplin R T, Anderson H L. Angew. Chem. Int. Ed., 2000, 39: 3456-3460
[9] Luo J, Xie Z, Lam J W Y, Cheng L, Chen H, Qiu C, Kwok H S, Zhan X, Liu Y, Zhu D, Tang B Z. Chem. Commun., 2001, 1740-1741
[10] Tang B Z, Zhan X, Yu G, Lee P P S, Liu Y, Zhu D. J. Mater. Chem., 2001, 11: 2974-2978
[11] Itami K, Ohashi Y, Yoshida J I. J. Org. Chem., 2005, 70: 2778-2792
[12] Nakatsuji S, Matsuda K, Uesugi Y, Nakashima K, Akiyama S, Katzer G, Fabian W. J. Chem. Soc., 1991, 6: 861-867
[13] Kim S, Zheng Q D, He G S, Bharali D J, Pudavar H E, Baev A, Prasad P N. Adv. Funct. Mater., 2006, 16: 2317-2323
[14] He J T, Xu B, Chen F P, Xia H J, Li K, Ye L, Tian W J. J. Phys. Chem. C, 2009, 113: 9892-9899
[15] Xu B, Fang H H, Dong Y J, Chen F P, Chen Q D, Sun H B, Tian W J. New J. Chem., 2010, 34: 1838-1842
[16] Dong Y J, Xu B, Zhang J B, Lu H G, Wen S P, Chen F P, He J T, Li B, Ye L, Tian W J. CrystEngComm, 2012, 14: 6593-6598
[17] Lu H G, Xu B, Dong Y J, Chen F P, Li Y W, Li Z F, He J T, Li H, Tian W J. Langmuir, 2010, 26: 6838-6844
[18] Dong Y J, Xu B, Zhang J B, Tan X, Wang L J, Chen J L, Lu H G, Wen S P, Li B, Ye L, Zou B, Tian W J. Angew. Chem. Int. Ed., 2012, 51: 10782-1078
[19] Xu B, He J T, Dong Y J, Chen F P, Yu W L, Tian W J. Chem. Commun., 2011, 47: 6602-6604
[20] Li H Y, Zhang X Q, Chi Z G, Xu B J, Zhou W, Liu S W, Zhang Y, Xu J R. Org. Lett., 2011, 13: 556-559
[21] Zhang X Q, Chi Z G, Zhang J Y, Li H Y, Xu B J, Li X F, Liu S W, Zhang Y, Xu J R. J. Phys. Chem. B, 2011, 115: 7606-7611
[22] Xu B, Zhang J B, Fang H H, Lu H G, Chen J L, Chen F P, Dong Y J, He J T, Xia H J, Chen Q D, Sun H B, Im C, Tian W J. unpublished result
[23] Lu H G, Su F Y, Mei Q, Zhou X F, Tian Y Q, Tian W J, Johnson R H. Polym. Chem., 2012, 50: 890-899
[24] Lu H G, Su F Y, Mei Q, Tian Y Q, Tian W J, Johnsona R H, Meldruma D R. J. Mater. Chem., 2012, 22: 9890-9900
[25] Hong Y N, Lam J W Y, Tang B Z. Chem. Soc. Rev., 2011, 40: 5361-5388
[26] Hong Y N, Lam J W Y, Tang B Z. Chem. Commun., 2009, 4332-4353
[27] Thomas S. Angew. Chem. Int. Ed., 2002, 41: 48-76
[28] Katharina R, Heike I S, Jürg H. Chem. Soc. Rev., 2005, 34: 22-30
[29] Robin T, Olga K. J. Am. Chem. Soc., 1982, 104: 5063-5070
[30] Hu R R, Lager E, Aguilar-Aguilar A, Liu J Z, Lam J W Y, Sung H H Y, Williams I D, Zhong Y C, Wong K S, Peña-Cabrera E, Tang B Z. J. Phys. Chem. C, 2009, 113: 15845-15853
[31] Cornil J, Beljonne D, Calbert J, Brédas J. Adv. Mater., 2001, 13: 1053-1067
[32] Kasha M, Rawls H R, Ashraf El-Bayoumi M. Pure Appl. Chem., 1965, 11: 371-392
[33] Michael D M, Alan J. H. Adv. Mater., 2000, 12: 1655-1668
[34] Kim S, Pudavar H E, Bonoiu A, Prasad P N. Adv. Mater., 2007, 19: 3791-3795
[35] Kim S, Ohulchanskyy T Y, Pudavar H E, Pandey R K, Prasad P N. J. Am. Chem. Soc., 2007, 129: 2669-2675
[37] Davis D A, Hamilton A, Yang J, Cremar L D, Gough D V, Potisek S L, Ong M T, Braun P V, Martínez T J, White S R, Moore J S, Sottos N R. Nature, 2009, 459: 68-72
[38] Wang Z L, Xu B, Zhang Lei, Zhang J B, Ma T H, Zhang J B, Fu X Q, Tian W J. Nanoscale, 2013, 5: 2065-2072
[39] Li X, Xu B, Lu H G, Wang Z L, Zhang J B, Zhang Y, Dong Y J, Ma K, Wen S P, Tian W J. Anal. Methods, 2013, 5: 438-441
[40] Wang L J, Xu B, Zhang J B, Dong Y J, Wen S P, Zhang H Y, Tian W J. Phys. Chem. Chem. Phys., 2013, 15: 2449-2458
[41] Yuan W Z, Gong Y, Chen S, Shen X Y, Lam J W Y, Lu P, Lu Y, Wang Z, Hu R, Xie N, Kwok H S, Zhang Y, Sun J Z, Tang B Z. Chem. Mater., 2012, 24: 1518-1528
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