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科学通报  2012 

一种改进的双费歇尔关环法合成吲哚[3,2-b]咔唑

DOI: 10.1360/972011-2194, PP. 510-513

Keywords: 咔唑,平面模块,共轭,半导体,聚合物

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Abstract:

含咔唑的共轭聚合物在聚合物发光二极管、聚合物太阳能电池、聚合物场效应晶体管等方面具有广泛的应用,已经成为光电功能材料研究领域的热点之一.具有平面结构的、含咔唑的共轭单体是构筑高载流子迁移率的聚合物的理想构筑基元.本文报道了一种改进的双费歇尔关环合成吲哚[3,2-b]咔唑的方法,提出了反应可能的机理,该方法将吲哚[3,2-b]咔唑的产率由文献报道的最高值26%提高到了51%.通过将吲哚[3,2-b]咔唑的5和11位进行烷基化,提高了其溶解性,使得该模块在普通溶剂中具有良好的溶解性.此外,采用一种简单有效的合成路线进一步制备了该模块2,8位的有机硼试剂,有望使其在合成共轭高分子半导体材料方面得到广泛的应用.

References

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[2]  Morin J F, Leclerc M, Adès D, et al. Polycarbazoles: 25 years of progress. Macromol Rapid Commun, 2005, 26: 761-778
[3]  Thomas K R, Lin J, Tao J T, et al. Light-Emitting carbazole derivatives: Potential electroluminescent materials. J Am Chem Soc, 2001,123: 9404-9411
[4]  Li J, Liu D, Li Y, et al. A high Tg carbazole-based hole-transporting material for organic light-emitting devices. Chem Mater, 2005, 17:1208-1212
[5]  Li Z A, Liu Y Q, Yu G, et al. A new carbazole-constructed hyperbranched polymer: Convenient one-pot synthesis, hole-transporting ability, and field-effect transistor properties. Adv Funct Mater, 2009, 19: 2677-2683
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[7]  Siove A, Adès D. Synthesis by oxidative polymerization with FeCl3 of a fully aromatic twisted poly(3,6-carbazole) with a blue-violet luminescence[J].Polymer.2004, 45:4045-4049
[8]  Iraqi A, Wataru I. Preparation of poly(9-alkylcarbazole-3,6-diyl)s via palladium catalysed cross-coupling reactions[J].Synth Met.2001, 119:159-160
[9]  Ostrauskaite J, Strohriegl P. Formation of macrocycles in the synthesis of Poly(N-(2-ethylhexyl)carbazol-3,6-diyl)[J].Macromol Chem Phys.2003, 204:1713-1718
[10]  Dong S, Li Z, Qin J. New carbazole-based fluorophores: Synthesis, characterization, and aggregation-induced emission enhancement. J Phys Chem B, 2009, 113: 434-441
[11]  Beaupré S, Boudreault P L T, Leclerc M. Solar-Energy production and energy-efficient lighting: Photovoltaic devices and white-lightemitting diodes using poly(2,7-fluorene), poly(2,7-carbazole), and poly(2,7-dibenzo silole) derivatives[J].Adv Mater.2010, 22:6-
[12]  Blouin N, Leclerc M. Poly(2,7-carbazole)s: Structure property relationships[J].Acc Chem Res.2008, 41:1110-1119
[13]  Boudreault P L T, Blouin N, Leclerc M. Poly(2,7-carbazole)s and related polymers. Adv Polym Sci, 2008, 212: 99
[14]  Li Y, Wu Y, Gardner S, et al. Novel peripherally substituted indolo[3,2-b]carbazoles for high-mobility organic thin-film transistors[J].Adv Mater.2005, 17:849-853
[15]  赵华平. 吲哚[3,2-b]咔唑衍生物的设计、合成和半导体性能. 博士学位论文. 济南: 山东大学, 2007. 45-51
[16]  何涛. 吲哚[3.[J].2-b]咔唑衍生物的设计、合成和薄膜场效应管性能的研究. 硕士学位论文. 济南: 山东大学.2009,:-
[17]  Nicolas B, Alexandre M, Salem W, et al. Optical, electrochemical, magnetic, and conductive properties of new polyindolocarbazoles and polydiindolocarbazoles. Macromol Chem Phys, 2006, 207: 166-174
[18]  Yu L, Yi W, Sandra G, et al. Novel peripherally substituted indolo[3,2-b]carbazoles for high-mobility organic thin-film transistors[J].Adv Mater.2005, 17:849-852
[19]  Larisa N Y, Jan B. Synthesis and alkylation of indolo[3,2-b]carbazoles[J].Tetrahedron.2003, 59:1265-1275

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