中文
Earlier issues
Announcement
More
Progress in Chemistry Previous Articles   Next Articles

• Review •

Optoelectronic Properties of Silole-Containing Polymers

Liu Zhitian1*, Hu Zhao1, Shen Zhi1, Hu Shuangqiang1, Wang Zixing2, Qi Xin1   

  1. 1. School of Materials Science and Engineering, Wuhan Institute of Technology, Wuhan 430074, China;
    2. Key Laboratory for Advanced Displays and System Application, Ministry of Education, Shanghai University, Shanghai 200072, China
  • Received: Revised: Online: Published:
PDF ( 1056 ) Cited
Export

EndNote

Ris

BibTeX

Siloles are a group of five-membered silacyclics, which have drawn much attention due to its unique electronic structures, molecule diversity and designability recently. High performance OLED can be made using small silole molecules as emitting materials or electron transfer materials. Silole-containing polymers have also attracted much attention of a number of chemists. Besides the high conductivity, many new properties have been found, such as highly efficient power conversion efficiency in plastic solar cells, fast carrier mobility in field-effect transistors (FET), high efficiency in polymeric light-emitting diodes (PLEDs), etc. Thus siloles are promising optoelectronic functional materials. In this review, the optoelectronic properties of silole-containing polymers are described according to the different structures of their parent compounds. Contents
1 Introduction
2 Substituted silole
2.1 Poly(1,1-silole)s
2.2 Poly(2,5-silole)s
2.3 Poly(3,4-silole)s
3 Dibenzosilole
4 Dithienosilole
5 Bis-silicon-bridged stilbene
6 Conclusion
Key words: silole, conjugated polymer, optoelectronic properties

CLC Number: 

[1] Yamaguchi S, Tamao K. Bull. Chem. Soc. Jpn., 1996, 69 :2327-2334
[2] Tamao K, Uchida M, Izumizawa T, Furukawa K, Yamaguchi S. J.Am. Chem. Soc., 1996, 118: 11974-11975
[3] Colomer E, Corriu R J P, Lheureux M. Chem. Rev., 1990, 90: 265-282
[4] Dubac J, Guerin C, Meunier P. The Chemistry of Organic Silicon Compounds, Vol. 2 (Eds. Rappoport Z, Apeloig Y). John Wiley & Sons, 1999. Chapter 34
[5] Yamaguchi S, Endo T, Uchida M, Izumizawa T, Furukawa K, Tamao K. Chem. Eur. J., 2000, 6: 1683-1692
[6] Sohn H, Huddleston R, Powell D R, West R, Oka K, Xu Y H. J. Am. Chem. Soc., 1999, 121: 2935-2936
[7] Chen J, Peng H, Law C C W, Dong Y, Lam J W Y, Williams I D, Tang B Z. Macromolecules, 2003, 36: 4319-4327
[8] Hermanns J, Schmidt B. J. Chem. Soc. Perkin Trans., 1998, (1): 2209-2230
[9] Wang E G, Li C, Mo Y, Zhang Y, Ma G, Shi W, Peng J B, Yang W, Cao Y. J. Mater. Chem., 2006, 16: 4133-4140
[10] Braye E H, Hubel W. Chem. Ind. (Lond.), 1959, 1250-1251
[11] Chen J W, Cao Y. Macromol. Rapid Commun., 2007, 28: 1714-1742
[12] Chen J W, Cao Y. Accounts of Chemical Research, 2009, 11:1709-1718
[13] Li Z, Dong Y Q, Lam J W Y, Sun J X, Qin A J, Haubler M, Dong Y P, Sung H H Y, Williams H S K, Tang B Z. Adv. Funct. Mater., 2009, 19: 905-917
[14] Murata H, Malliaras G G, Uchida M, Shen Y, Kafafi Z H. Chem. Phys. Lett. 2001, 339, 161-166
[15] 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
[16] Li Z, Dong Y Q, Mi B X, Tang Y H, Haussler M, Tong H, Dong Y P, Lam J W Y, Ren Y, Sung H H Y, Wong K S, Gao P, Williams L D, Kwok H S, Tang B Z.J. Phys. Chem. B, 2005, 109: 10061-10066
[17] Hong Y N, Lam J W Y, Tang B Z. Chem. Commun., 2009, (29): 4332-4353
[18] Palilis L C, Makinen A J, Uchida M, Kafafi Z H. Appl. Phys. Lett., 2003, 82(14): 2209-2211
[19] Oshita J, Kai H, Takata A, Iida T, Kunai A, Ohta N, Komaguchi K, Shiotani M, Adachi A, Sakamaki K, Okita K. Organometallics, 2001, 20: 4800-4805
[20] Chen J W, Xu B, Yang K X, Cao Y, Sung H H Y, Williams L D, Tang B Z.J. Phys. Chem. B, 2005,109: 17086-17093
[21] Lee J, Yuan YY, Kang Y J, Jia W L, Lu Z H, Wang S N. Adv. Func. Mater., 2006, 16: 681-686
[22] Tamao K, Yamaguchi S, Shiozaki M, Nakagawa Y, Ito Y. J. Am. Chem. Soc.,1992, 114 : 5867-5869
[23] Chen J, Law C C W, Lam J W Y, Dong Y, Lo S M F, Williams I D, Zhu D, Tang B Z. Chem. Mater., 2003, 15: 1535-1546
[24] Liu Z T, Lei G T, Yu Z B, Yuan W, Pei Q B, Chen J W, Cao Y. PMSE Preprints, 2009, 101: 958-959
[25] Mo Y Q, Tian R Y, Shi W, Cao Y. Chem. Commun., 2005, 4925-4926
[26] Liu M S, Luo J, Jen A K Y. Chem. Mater., 2003,15: 3496-3500
[27] Huo L J, Chen H Y, Hou J H, Chen T L, Yang Y. Chem. Commun, 2009, 5570-5572
[28] Chu T Y, Lu J P, Beaupre S,Zhang Y U, Pouliot J R, Wakim S,Zhou J Y, Leclerc M, Li Z, Ding J F, Tao Y. J.Am. Chem. Soc., 2011, 133(12): 4250-4253
[29] Du X B, Wang Z Y. Chem.Commun., 2011, 47: 4276-4278
[30] Sohn H, Calhoun R W, Sailor M J, Trogler W C. Angew. Chem. Int. Ed., 2001, 40: 2104-2015
[31] Usta H, Lu G, Facchetti A, Marks T J. J. Am. Chem. Soc., 2006, 128: 9034-9035
[32] Yamaguchi S, Jin R Z, Tamao K. J. Am. Chem. Soc., 1999, 121: 2937-2938
[33] Chen J W, Xie Z L, Lam J W K, Law C C W, Tang B Z. Macromolecules, 2003, 36: 1108-1117
[34] Shinar J, Ijadi-Maghsoodi S, Ni Q X, Pang Y, Barton T J. Synth. Met., 1989, 28: 593-598
[35] Barton T J, Ijadi-Maghsoodi S, Pang Y. Macromolecules, 1991, 24: 1257-1260
[36] Tamao K, Yamaguchi S, Shiro M. J. Am. Chem. Soc., 1994,116: 11715-11722
[37] Yamaguchi S, Jin R Z, Itami Y, Goto T, Tamao K. J. Am. Chem. Soc., 1999, 121: 10420-10421
[38] Wang F, Luo J, Yang K S, Chen J W, Huang F, Cao Y. Macromolecules, 2005, 38: 2253-2260
[39] Wang F, Luo J, Chen J W, Huang F, Cao Y. Polymer, 2005, 46: 8422-8429
[40] Wang Y, Hou L T, Yang K X, Chen J W, Wang F, Cao Y. Macromol. Chem. Phys., 2005, 206: 2190-2198
[41] Liu Z T, Wang L, Chen J W, Wang F, Ouyang X Y, Cao Y. J. Polym. Sci. Part A: Polym. Chem., 2007, 45: 756-767
[42] Liu Y Q, Chen Z, Chen J W, Wang F, Cao Y. Polymer Bulletin, 2007, 59: 31-44
[43] Liu Z T, Zou J H, Chen J W, Huang L, Peng J B, Cao Y. Polymer, 2008, 49: 1604-1610
[44] 刘治田(Liu Z T), 邹建华(Zou J H), 陈军武(Chen J W), 刘永强(Liu Y Q), 彭俊彪(Peng J B), 曹镛(Cao Y). 高分子学报(Acta Polymerica Sinica), 2009, 9: 845-851
[45] Horst S, Evans N R, Bronstein H A, Williams C K. J. Polym. Sci. Part A: Polym. Chem., 2009, 47: 5116-5125
[46] Gilman H, Gorsich R D. J. Am. Chem. Soc., 1955, 77: 6380-6381
[47] Chen R F, Fan Q L, Zheng C. Org. Lett., 2006, 8: 203-205
[48] Liu Y, Stringfellow T C, Ballweg D. J. Am. Chem. Soc., 2002, 124: 489-493
[49] Deerenberg S, Schakel M, de Keijzer A H J F, Kraneburg M, Lutz M, Spek A L, Lammertsma K. Chem. Commun., 2002, 348-349
[50] Chan K L, McKiernan M J, Towns C R, Holmes A B. J. Am. Chem. Soc., 2005, 127: 7662-7663
[51] 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, 5766-5768
[52] Zhang X, Jiang C, Mo Y, Xu Y, Shi H, Cao Y. Appl. Phys. Lett., 2006, 88: 629-633
[53] Chen R F, Fan Q L, Liu S J, Zhu R, Pu K Y, Huang W. Synth. Met., 2006, 156: 1161-1167
[54] Wang E G, Li C, Peng J B, Cao Y. J. Polym. Sci. Part A: Polym. Chem., 2007, 45 (21): 4941-4949
[55] Boudreault P L T, Alexandre M, Mario L. Macromol. Rapid Commun., 2007, 28(22): 2176-2179
[56] Lu G, Usta H, Risko C, Wang L, Facchetti A, Ratner M A, Marks T J. J. Am. Chem. Soc., 2008, 130(24): 7670-7685
[57] Li L C, Xu C H, Li S H. Tetrahedron Letters, 2010, 51(4): 622-624
[58] Ohshita J, Nodono M, Watanabe T, Ueno Y, Kunai A, Yamashita Y K, Ishikawa M. J. Organomet. Chem.,1998, 553: 487-491
[59] Usta H, Lu G, Facchetti A, Marks T J. J. Am. Chem. Soc., 2006, 128: 9034-9035
[60] Ohshita J, Hamamoto D, Kimura K, Kunai A. J. Organomet. Chem., 2005, 690: 3027-3032
[61] Chen W, Ijadi-Maghsoodi S, Barton T J. Polym. Prepr. Am. Chem. Soc., Div. Polym. Chem., 1997, 38: 189-190
[62] Zhang Z W, Li J, Huang B, Qin J G. Chemistry Letters, 2006, 35(8): 958-959
[63] Liao L, Cirpan A, Chu Q H, Karasz F E, Pang Y. J. Polym. Sci. Part A: Polym. Chem., 2007, 45(10): 2048-2058
[64] Ohshita J, Kimura K, Lee K H, Kunai A, Kwak Y W, Son E C, Kunugi Y. J. Polym. Sci. Part A: Polym. Chem., 2007, 45(20): 4588-4596
[65] Ohshita J J, Kai H, Kimura K, Lee K, Kunai A. Polymer Journal, 2009, 41(6): 482-485
[66] Kumar R, Wudl F. Abstracts of Papers, 239th ACS National Meeting, San Francisco, CA, United States, March 21-25, 2010
[67] He Y J, Zhao G J, Zhang M J, Min J, Li Y F. Synth. Met., 2010, 160(9/10): 1045-1049
[68] Zhang M J, Hai J, Guo X, He Y J, Zhang Z G, Min J, Zhang J, Zhao G J, Zhan X W, Li Y F. Macromolecules, 2010, 43(13): 5706-5712
[69] Ding J F, Song N H, Zhao L. Chem. Commun., 2010, 46:8668-8670
[70] Serby M, Ijadi-Maghsoodi S, Barton T J. 33rd Symposium on Organosilicon Chemistry, Saginaw, MI, 2000. PA-35
[71] Yamaguchi S, Xu C,Tamao K. J. Am. Chem. Soc., 2003, 125: 13662-13663
[72] Xu C H, Yamada H, Wakamiya A, Yamaguchi S, Tamao K. Macromolecules, 2004, 37(24): 8978-8983
[1] Jin Du, Rui Liao, Xinglin Zhang, Huibin Sun, Wei Huang. The Classification of Electrofluorochromism Materials and Color Change Mechanisms [J]. Progress in Chemistry, 2018, 30(2/3): 286-294.
[2] Honglei Wang, Wenzhen Lv, Xingxing Tang, Lingfeng Chen, Runfeng Chen, Wei Huang. Two-Dimensional Perovskites and Their Applications on Optoelectronic Devices [J]. Progress in Chemistry, 2017, 29(8): 859-869.
[3] Lu Xiaomei, Li Jie, Hu Wenbo, Deng Weixing, Fan Quli, Huang Wei. Recent Advances of the Water-Soluble Conjugated Polymer Brushes [J]. Progress in Chemistry, 2016, 28(4): 528-540.
[4] Sun Pengfei, Hou Huanzhi, Fan Quli, Huang Wei. Synthesis and Application of Water-Soluble Conjugated Glycopolymer [J]. Progress in Chemistry, 2016, 28(10): 1489-1500.
[5] Ma Yun, Zhou Yan, Du Wenqi, Miao Zhihui, Qi Zhengjian*. The Application of DNA Biosensor Based on Conjugated Polymers [J]. Progress in Chemistry, 2015, 27(12): 1799-1807.
[6] Chen Yun, Shao Ya, Fan Lijuan. Fluorescent Color Tuning of Conjugated Polymer Materials: Mechanisms and Methods [J]. Progress in Chemistry, 2014, 26(11): 1801-1810.
[7] Ren Xiaojie, Lu Xiaomei, Fan Quli, Huang Wei. Conjugated Polymers with Two-Photon Absorption for Bioimaging [J]. Progress in Chemistry, 2013, 25(10): 1739-1750.
[8] Chen Zhouqun, Ma Chang-Qi. Synthesis of Poly(3-Alkylthiophene)s [J]. Progress in Chemistry, 2013, 25(07): 1166-1176.
[9] Cai Xiaohui, Shi Lin, Liu Xingfen*, Huang Yanqin, Fan Quli, Huang Wei*. Functionalized Conjugated Polymers and Their Application in the Biological and/or Chemical Analysis [J]. Progress in Chemistry, 2013, 25(06): 975-989.
[10] Zhang Lihong, Yu Qingcai, Wan Junhua*. Silole-Containing Polymer Photovoltaic Donor Materials [J]. Progress in Chemistry, 2013, 25(05): 752-760.
[11] Zhang Huijing, Hou Xin. Development of Organic Polymer/Inorganic Semiconductor Hybrid Solar Cells [J]. Progress in Chemistry, 2012, 24(11): 2106-2115.
[12] Yang Zhenglong, Bu Yilong, Chen Qiuyun. High Efficiency Low Band Gap Conjugated Polymer Materials for Solar Cells [J]. Progress in Chemistry, 2011, 23(12): 2607-2616.
[13] Zhu Chunlei, Yang Qiong, Liu Libing, Wang Shu. Conjugated Polymers for Sensitive Chemical Sensors [J]. Progress in Chemistry, 2011, 23(10): 1993-2002.
[14] Liu Yong Shu Yuanjie Liu Xueyong Xiong Ying Zhong Fachun Sun Yi. Application of Molecular Imprinting and Fluorescence Analysis Techniques in Explosive Detection [J]. Progress in Chemistry, 2009, 21(12): 2712-2717.
[15] Li Di Zhang Long Fan Quli Huang Wei. Self-Assembly of Conjugated Rod-Coil Block Copolymers [J]. Progress in Chemistry, 2009, 21(12): 2660-2673.