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Progress in Chemistry 2009, Vol. 21 Issue (12): 2605-2612 Previous Articles   Next Articles

• Review •

Optoelectronic Materials of Organoboron π-Conjugated Systems

Zhao Cuihua**;  Zhao Yihong;  Lin Jimao   

  1. (School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, China)
  • Received: Revised: Online: Published:
  • Contact: Zhao Cuihua E-mail:chzhao@sdu.edu.cn
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The boron-containing π-conjugated materials have attracted considerable research interest in recent years due to their unique optoelectronic properties, which stem from the characteristic features of boron element, such as the p-π* conjugation between the vacant p orbital on the boron atom with π* orbital of the π-conjugated framework, the high Lewis acidity to coordinate with Lewis bases, as well the steric bulk arising from the aryl substituent on the boron atom to get enough kinetic stability. It has been demonstrated that this kind of materials are applicable in a wide range fields, such as nonlinear optics, two-photon absorption and emission materials, electron-transporting and emissive materials in organic light-emitting devices as well as chemosensors. Research progress in the oganoboron π-conjugated materials are reviewed in this paper, in terms of the molecular structures of the π-conjugated systems, including the linear π-conjugated systems with boryl groups at the terminal positions, the starburst π-conjugated systems containing boron atoms at the center, the polymeric π-conjugated systems containing boron atoms in the main chain, the boron-bridged ring-fused π-conjugated systems, as well as the π-conjugated systems with boryl groups at the side positions. The further development tendency of this field is also prospected.

Contents
1 Introduction
2 Research progress in the optoelectronic materials of organoboron π-conjugated systems
2.1 Linear π-conjugated systems with boryl groups at the terminal positions
2.2 The starburst π-conjugated systems containing boron atoms at the center
2.3 The polymeric π-conjugated systems containing boron atoms in the main chain
2.4 The boron-bridged ring-fused π-conjugated systems
2.5 The π-conjugated systems containing boryl groups at the side positions
3 Prospects

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[ 1 ]  Yamaguchi S , Wakamiya A. Pure Appl . Chem. , 2006 , 78 : 1413 — 1424
[ 2 ]  Entwistle C D , Marder T B. Angew. Chem. Int . Ed. , 2002 , 41 : 2927 —2931
[ 3 ]  Entwistle C D , Marder TB. Chem. Mater. , 2004 , 16 : 4574 —4585
[ 4 ]  J¾ kle F. Coord. Chem. Rev. , 2006 , 250 : 1107 —1121
[ 5 ]  Tamao K, Yamaguchi S , Uchida M, Izumizawa T, Furukawa K. Organosilicon Chemistry Ⅳ. From Molecules to Materials ( Eds. Auner N , Weis J ) . Weinheim: Wiley2VCH Verlag GmbH , 2000. 245 —251
[ 6 ]  Dyer P W, Réau R. Functional Organic Materials : Syntheses , Strategies and Applications ( Eds. Müller J J , Bunz U H F) . Weinheim: Wiley2VCH Verlag GmbH , 2007. 119 —177
[ 7 ]  Wittig G, Herwig W. Chem. Ber. , 1955 , 88 : 962 —976
[ 8 ]  Williams J L R , Grisdale P J , Doty J C. J . Org. Chem. , 1971 , 36 : 544 —549
[ 9 ]  Doty J C , Babb B , Grisdale P J , Glogowski M, Williams J L R. J . Organomet . Chem. , 1972 , 38 : 229 —236
[10 ]  Glogowski M E , Williams J L R. J . Organomet . Chem. , 1981 , 216 : 1 —8
[11 ]  Kaim W, Schultz A. Angew. Chem. Int . Ed. , 1984 , 23 : 615 — 616
[12 ]  Schutlz A , Kaim W. Chem. Ber. , 1989 , 122 : 1863 —1868
[13 ]  Yuan Z, Tailor NJ , Marder TB , Williams I D , Kurtz S K, ChengL T. J . Chem. Soc. Chem. Commun. , 1990 , 1489 —1492
[14 ]  Yuan Z, Collings J C , Taylor N J , Marder T B , Jardin C , Halet J F. J . Solid State Chem. , 2000 , 154 : 5 —12
[15 ]  Yuan Z, Taylor NJ , Sun Y, Marder TB , Williams I D , ChengL T. J . Organomet . Chem. , 1993 , 449 : 27 —37
[16 ]  Yuan Z, Taylor N J , Ramachandran R , Marder T B. Appl . Organomet . Chem. , 1996 , 10 : 305 —316
[17 ]  Lequan M, Lequan R M, Ching C K. J . Mater. Chem. , 1991 , 1 : 997 —999
[18 ]  Lequan M, Lequan R M, Ching K C , Barzoukas M, Fort A , Lahoucine H , Bravic B , Chasseau D , Gaultier J . J . Mater. Chem. , 1992 , 2 : 719 —725
[19 ]  Lequan M, Lequan R M, Ching K C , Callier A C , Barzoukas M, Fort A. Adv. Mater. Opt . Electron. , 1992 , 1 : 243 —247
[20 ]  Branger C , Lequan M, Lequan R M, Barzoukas M, Fort A. J . Mater. Chem. , 1996 , 6 : 555 —558
[21 ]  Parthenopoulos D A , Rentzepis P M. Science , 1989 , 245 : 843 — 845
[22 ]  Denk W, Strickler J H , Webb W W. Science , 1990 , 248 : 73 —76
[23 ]  Belfield KD , Ren XB , van Stryland E W, Hagan D J , Dubikovsky V , Misak E J . J . Am. Chem. Soc. , 2000 , 122 : 1217 —1218
[24 ]  Silly M G, Porrès L , Mongin O , Chollet P A , Blanchard2Desce M. Chem. Phys.Lett . , 2003 , 379 : 74 —80
[25 ]  Liu Z Q , Fang Q , Wang D , Xue G, Yu W T, Shao Z S , Jiang M H. Chem. Commun. , 2002 , 2900 —2901
[26 ]  Liu Z Q , Fang Q , Wang D , Cao D X, Xue G, Yu W T, Lei H. Chem. Eur. J . , 2003 , 9 : 5074 —5084
[27 ]  Liu Z Q , Fang Q , Cao D X, Wang D , Xu GB. Org. Lett . , 2004 , 6 : 2933 —2936
[28 ]  刘志强(Liu Z Q) , 方奇( Fang Q) , 王东(Wang D) , 薛刚(Xue G) , 曹笃霞(Cao D X) , 于文涛(Yu W T) , 夏光明(Xia GM) . 化学学报(Acta Chimica Sinica) , 2003 , 61 : 1449 —1454
[29 ]  刘志强(Liu Z Q) , 曹笃霞(Cao D X) , 方奇( Fang Q) , 刘国群 (Liu GQ) , 许贵宝(Xu GB) . 化学学报(Acta Chimica Sinica) , 2004 , 62 : 2103 —2108
[30 ]  曹笃霞(Cao D X) , 刘志强(Liu Z Q) , 王东(Wang D) , 方奇 (Fang Q) . 化学学报(Acta Chimica Sinica) , 2005 , 63 : 1415 — 1420
[31 ]  Liu Z Q , Shi M, Li F Y, Fang Q , Chen Z H , Yi T, Huang C H. Org. Lett . , 2005 , 7 : 5481 —5484
[32 ]  Noda T, Shirota Y. J . Am. Chem. Soc. , 1998 , 120 : 9714 —9715
[33 ]  Nota T, Ogawa H , Shirota Y. Adv. Mater. , 1999 , 11 : 283 —285
[34 ]  Mazzeo M, Vitale V , Sala F D , Anni M, Barbarella G, Favaretto L , Sotgiu G, Cingolani R , Gigli C. Adv. Mater. , 2005 , 17 : 34 —39
[35 ]  Shirota Y, Kinoshita M, Nota T, Okumoto K, Ohara T. J . Am. Chem. Soc. , 2000 , 122 : 11021 —11022
[36 ]  Doi H , Kinoshita M, Okumoto K, Shirota Y. Chem. Mater. , 2003 , 15 : 1080 —1089
[37 ]  Yamaguchi S , Akiyama S , Tamao K. J . Am. Chem. Soc. , 2000 , 122 : 6335 —6336
[38 ]  Yamaguchi S , Akiyama S , Tamao K. J . Am. Chem. Soc. , 2001 , 123 : 11372 —11375
[39 ]  Yamaguchi S , Shirasaka T, Tamao K. Org. Lett . , 2000 , 2 : 4129 — 4132
[40 ]  Jia WL , Song D , Wang S. J . Org. Chem. , 2003 , 68 : 701 —705
[41 ]  Matsumi N , Naka K, Chujo Y. J . Am. Chem. Soc. , 1998 , 120 : 5112 —5113
[42 ]  Matsumi N , Naka K, Chujo Y. J . Am. Chem. Soc. , 1998 , 120 : 10776 —10777
[43 ]  Sundaraman A , Victor M, Varughese R , J¾ kle F. J . Am. Chem. Soc. , 2005 , 127 : 13748 —13749
[44 ]  Yamaguchi S , Shirasaka T, Akiyama S , Tamao K. J . Am. Chem. Soc. , 2002 , 124 : 8816 —8817
[45 ]  Brière J F , CÉ tèM. J . Phy. Chem. B , 2004 , 108 : 3123 —3129
[46 ]  Wakamiya A , Mishima K, Ekawa K, Yamaguchi S. Chem. Commun. , 2008 , 579 —581
[47 ]  Kim S , Song K H , Kang S O , Ko J . Chem. Commun. , 2004 , 68 — 69
[48 ]  Elbing M, Bazan GC. Angew. Chem. Int . Ed. , 2008 , 47 : 834 — 838
[49 ]  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 , Brédas J L , LÊgdlund M, Salaneck W R. Nature , 1999 , 397 : 121 —128
[50 ]  Chen C T. Chem. Mater. , 2004 , 16 : 4389 —4400
[51 ]  Zhao C H , Wakamiya A , Inukai Y, Yamaguchi S. J . Am. Chem. Soc. , 2006 , 128 : 15934 —15935
[52 ]  Zhao C H , Wakamiya A , Yamaguchi S. Macromolecules , 2007 , 40 : 3898 —3900
[53 ]  Wakamiya A , Mori K, Yamaguchi S. Angew. Chem. Int . Ed. , 2007 , 119 : 4351 —4354
[54 ]  Li H , Sundaraman A , Venkatasubbaiah K, J¾ kle F. J . Am. Chem. Soc. , 2007 , 129 : 5792 —5793

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