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Progress in Chemistry DOI: 10.7536/PC121241 Previous Articles   Next Articles

• Review •

Synthesis and Applications of 1,8-Functionalized Heterofluorenes for Organic Electronics

Cao Jinzhu1, Wang Zhixiang1, Chen Runfeng*1,2, Li Huanhuan1, Zheng Chao1, Huang Wei*2   

  1. 1. Key Laboratory for Organic Electronics & Information Displays and Institute of Advanced Materials, Nanjing University of Posts & Telecommunications, Nanjing 210023, China;
    2. Jiangsu-Singapore Joint Research Center for Organic/Bio- Electronics & Information Displays and Institute of Advanced Materials, Nanjing University of Technology, Nanjing 211816, China
  • Received: Revised: Online: Published:
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Heterofluorenes, achieved by substituting the sp3-hybridized carbon of fluorene with oxygen, sulfur, silicon, nitrogen, phosphor etc., are a series of very interesting optoelectronic materials. They have not only many highly effective ways to modify the electronic structures and properties through the particular interactions between the heteroatom and the π-conjugated system, but also show different modification properties at different substitution positions due to the influence of the heteroatoms. 1,8-Functionalization inspires new properties from widely used materials although the synthesis is always difficult. Owing to the wide spread progress of heterofluorenes and the 1,8-functionalization strategy, 1,8-functionalized heterofluorenes have received increasing attention in organic optical and electronic materials and devices recently. Herein, we summarized the basic principles of the molecular design, material synthesis, structure-property relations, and optoelectronic device applications of 1,8-functionalized heterofluorenes. The different synthetic methods of various 1,8-functionalized heterofluorenes are reviewed and presented according to different effects of different heteroatoms. Besides, the applications of 1,8-functionalized heterofluorenes as host materials for phosphorescent organic light emitting diodes, as electroluminescent materials for organic light emitting diodes, as photovoltaic materials for solar cells, and as functional ligands for organic metals are discussed in detail. Finally, the existing key problems and the future development of 1,8-functionalized heterofluorenes are also outlined and suggested. Contents
1 Introduction
2 Synthesis of 1,8-functionalized heterofluorenes
2.1 Direct synthetic methods
2.2 Indirect synthetic methods
3 Applications of 1,8-functionalized heterofluorenes
3.1 Organic electroluminescent materials
3.2 Photovoltaic materials
3.3 Ligands
4 Conclusion and outlook

Key words: fluorene, heterofluorene, 1,8-functionalization, synthesis, organic optoelectronic materials

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[1] Gross M, Müller D C, Nothofer H G, Scherf U, Neher D, Brauchle C, Meerholz K, Nothofer H G. Nature, 2000, 405: 661-665
[2] Sun Y R, Giebink N C, Kanno H, Ma B W, ThompsonM E, Forrest S R. Nature, 2006, 440(7086): 908-912
[3] Lewis N S. Science, 2007, 315(5813): 798-801
[4] Kim J Y, Lee K, Coates N E. Science, 2007, 317: 222-225
[5] Brabec C J, Sariciftci N S, Hummelen J C. Adv. Funct. Mater., 2001, 11: 15-26
[6] Coakley K M, McGehee M D. Chem. Mater., 2004, 16: 4533-4542
[7] 何有军(He Y J), 李永舫(Li Y F). 化学进展(Prog. Chem.), 2009, 21(11): 2303-2318
[8] Dimitrakopoulos C D, Malenfant P R L. Adv. Mater., 2002, 14: 99-117
[9] Liu Y, Miao Q, Zhang S W, Huang X B, Zheng L F, Cheng Y X. Macromol. Chem. Phys., 2008, 209: 685-694
[10] Zeng G, Yu W L, Chua S J, Huang W. Macromolecules, 2002, 35 (18): 6907-6914
[11] Chen P, Yang G Z, Huang W. Polym. Int., 2006, 55(5): 473-490
[12] Chen R F, Zheng C, Fan Q L, Huang W. J. Comput. Chem., 2007, 28(13): 2091-2101
[13] Chen R F, Zhu R, Fan Q L, Huang W. Org. Lett., 2008, 10(13): 2913-2916
[14] Brunner K, Dijken V A, Borner H, Bastiaansen J J A M, Kiggen N M M, Langeveld B M W. J. Am. Chem. Soc., 2004, 126 (19): 6035-6042
[15] Chan K L, McKiernan M J, Towns C R, Holmes A B. J. Am. Chem. Soc., 2005, 127 (21): 7662-7663
[16] Mak C S K, Hayer A, Pascu S I, Watkins S E, Holmes A B, Kohler A, Friend R H. Chem. Commun., 2005, (7): 4708-4710
[17] Mo Y Q, Tian R Y, Shi W, Cao Y. Chem. Commun., 2005, 4925-4926
[18] Chan K L, Watkins S E, Mak C S K, McKiernan M J, Towns C R, Pascu S I, Holmes A B. Chem. Commun., 2005, (46): 5766-5768
[19] Chen J W, Cao Y. Macromol. Rapid Commun., 2007, 28: 1714-1742
[20] Yan M K, Tao Y, Chen R F, Zheng C, An Z F, Huang W. RSC Advances, 2012, 2: 7860-7867
[21] Morin J F, Leclerc M, Ades D, Siove A. Macromol. Rapid Commun., 2005, 26: 761-778
[22] Dao L H, Leclerc M, Guay J, Chevalier J W. Synth. Met., 1989, 29: 377-382
[23] Morin J F, Leclerc M. Macromolecules, 2001, 34: 4680-4682
[24] Michinobu T, Osako H, Shigehara K. Macromolecules, 2009, 42: 8172-8180
[25] Chen R F, Xie G H, Zhao Y, Zhang S L, Yin J, Liu S Y, Huang W. Org. Electron., 2011, 12: 1619-1624
[26] 许运华(Xu Y H), 彭俊彪(Peng J B), 曹镛(Cao Y). 化学进展(Prog. Chem.), 2006, 18(4): 389-398
[27] Piatek P, Lynch V M, Sessler J L. J. Am. Chem. Soc., 2004, 126: 16073-16076
[28] Chmielewski M J, Charon M, Jurczak J. Org. Lett., 2004, 6: 3501-3504
[29] Thangadurai T D, Singh N J, Hwang I C. J. Org. Chem., 2007, 72: 5461-5464
[30] Chen R F, Liu L Y, Fu H, Zheng C, Xu H, Fan Q L, Huang W. J. Phys. Chem. B, 2011, 115(2): 242-248
[31] Schwartz E B, Knobler C B, Cram D J. J. Am. Chem. Soc., 1992, 114: 10775-10784
[32] Korang J, Grither W R, McCulla R D. J. Am. Chem. Soc., 2010, 132: 4466-4476
[33] Han C M, Xie G H, Xu H, Zhang Z S, Yu D H, Zhao Y, Yan P F, Deng Z P, Li Q, Liu S Y. Chem. Eur. J., 2011, 17: 445-449
[34] Han C M, Xie G H, Li J, Zhang Z S, Xu H, Deng Z P, Zhao Y, Yan P F, Liu S Y. Chem. Eur. J., 2011, 17: 8947-8956
[35] Ren Z J, Zhang R B, Yan S K. J. Mater. Chem., 2011, 21: 7777-7781
[36] Wang L, Wu Z Y, Wong W Y, Cheah K W, Huang H. Org. Electron., 2011, 12: 595-601
[37] Saito M, Tanikawa T, Tajima T, Guo J D, Nagase S. Tetrahedron Lett., 2010, 51: 672-675
[38] Britovsek G J P, Gibson V C, Hoarau O D, Spitzmesser S K, White A J P, Williams D J. Inorg. Chem., 2003, 42: 3454-3465
[39] Gibson V C, Spitzmesser S K, White A J P, Williams D J. Dalton Trans., 2003, 13: 2718-2727
[40] Mudadu M S, Singh A N, Thummel R P. J. Org. Chem., 2008, 73: 6513-6520
[41] Michinobu T, Osako H, Shigehara K. Macromol. Rapid Commun., 2008, 29: 111-116
[42] Fujita H, Michinobu T. Chem. Phys., 2012, 213: 447-457
[43] Widhalm M, Mereiter K. Tetrahedron: Asymmetry, 2006, 17: 1355-1369
[44] Thansandote P, Lautens M. Chem. Eur. J., 2009, 15: 5874-5883
[45] Wei Y, Yoshikai N. Org. Lett., 2011, 13: 5504-5507
[46] Xu H, Fan L L. Chem. Pharm. Bull., 2008, 56: 1496-1498
[47] Ogawa S, Tajiri Y, Furukawa N. Bull. Chem. Soc. Jpn., 1991, 64: 3182-3184
[48] Wehmschulte R J, Khan M A, Hossain S I. Inorg. Chem., 2001, 40: 2756-2762
[49] Diaz A A, Young J D, Khan M A, Wehmschulte R J. Inorg. Chem., 2006, 45: 5568-5575
[50] Diaz A A, Buster B, Schomlsch D, Khan M A, Baum J C, Wehmschulte R J. Inorg. Chem., 2008, 47: 2858-2863
[51] Geramita K, McBee J, Tilley T D. J. Org. Chem., 2009, 74: 820-829
[52] Li B J, Tian S L, Fang Z, Shi Z H. Angew. Chem. Int. Ed., 2008, 47: 1115-1118
[53] Li Z P, Li C J. J. Am. Chem. Soc., 2005, 127: 3672-3673
[54] Li Z P, Li C J. J. Am. Chem. Soc., 2005, 127: 6968-6969
[55] Zhang S L, Chen R F, Yin J, Liu F, Jiang H J, Shi N E, An Z F, Ma C, Liu B, Huang W. Org. Lett., 2010, 15(12): 3438-3441
[56] 陈润锋(Chen R F), 郑超(Zheng C), 范曲立(Fan Q L), 黄维(Huang W). 化学进展(Prog. Chem.), 2010, 22(4): 696-705
[57] Romero B, Schaer M, Leclerc M, Ades D, Siove A, Zuppiroli L. Synth. Met., 1996, 80: 271-277
[58] Jenekhe S A, Yi S J. Appl. Phys. Lett., 2000, 77: 2635- 2637
[59] Boudreault P L T, Blouin N, Leclerc M. Adv. Polym. Sci., 2008, 212: 99-124
[60] Blouin N, Leclerc M. Acc. Chem. Res., 2008, 41: 1110- 1119
[61] Yamaguchi S, Shirasaka T, Akiyama S, Tamao K. J. Am. Chem. Soc., 2002, 124 (30): 8816-8817
[62] Wakamiya A, Mishima K, Ekawa K, Yamaguchi S. Chem. Commun., 2008, (5): 579-581
[63] Mo Y Q, Tian R Y, Shi W, Cao Y. Chem. Commun., 2005, (39): 4925-4926
[64] Wang E, Li C, Pieng J, Cao Y. J. Polym. Sci. PartA: Polym. Chem., 2007, 45: 4941-4949
[65] Boudreault P L T, Michaud A, Leclerc M. Macromol. Rapid Commun., 2007, 28: 2176-2179
[66] Chen R F, Fan Q L, Liu S J, Zhu R, Pu K Y, Huang W. Synth. Met., 2006, 156: 1161-1167
[67] Kobayashi S, Noguchi T, Tsubata Y, Kitano M, Doi S, Ueoka T, Nakazono A. JP2003 231741
[68] Geramita K, McBee J, Tilley T D. J. Org. Chem., 2009, 74(2): 820-829
[69] Geramita K, McBee J, Tao Y F. Chem. Commun., 2008, (41): 5107-5109
[70] Makioka Y, Hayashi T, Tanaka M J. Chem. Lett., 2004, 33(1): 44-45
[71] Chen F C, Chang S C, He G F. J. Poly. Sci. Pol. Phys., 2003, 41: 2681-2690
[72] Yin J, Zhang S L, Chen R F, Ling Q D, Huang W. Phys. Chem. Chem. Phys., 2010, 12(47): 15448-15458
[73] Han C M, Zhang Z S, Xu H, Yue S Z, Li J, Yan P R, Deng Z P, Zhao Y, Yan P F, Liu S Y. J. Am. Chem. Soc., 2012, 134: 19179-19188
[74] Forrest S R. Nature, 2004, 428: 911-918
[75] Chen J W, Cao Y. Macromol. Rapid Commun., 2007, 28: 1714-1742
[76] Whittell G R, Manners I. Adv. Mater., 2007, 19(21): 3439-3468
[77] Mudadu M S, Singh A N, Thummel R P. J. Org. Chem., 2008, 73: 6513-6520
[78] Arnold L, Norouzi-Arasi H, Wagner M, Enkelmann V, Müllen K. Chem. Commun., 2010, 47: 970-972
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