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Progress in Chemistry 2010, Vol. 22 Issue (01): 113-118 Previous Articles   Next Articles

• Invited Article •

Synthesis and Photoelectric Device of Polynaphthalene

Huang Meirong; Gao Peng; Li Xingui**   

  1. (Institute of Materials Chemistry, Key Laboratory of Advanced Civil Engineering Materials of the Ministry of Education, College of Materials Science and Engineering, Tongji University, Shanghai 200092,China)
  • Received: Revised: Online: Published:
  • Contact: Li Xingui E-mail:adamxgli@yahoo.com
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The development progress and the achievements in chemical preparation of polynaphthalene are systematically reviewed and summarized, including oxidative polycondensation of naphthalene monomer by Lewis acid catalysts developed in the last century and Yamamoto and Suzuki methods of naphthalene derivatives developed recently. It is pointed out that naphthalene-based Grignard metathesis is the effective way to obtain polynaphthalene having definite structure with high yield, while plasma deposition can directly form film which accordingly avoids the intractability arising from difficult dissolution and melting of polynaphthalene. Especially through Yamamoto and Suzuki methods, polynaphthalene derivatives with excellent solubility and high PL quantum efficiency up to 0.96 can be obtained. Polynaphthalene with one-dimensional graphite structure can be produced by coupling naphthalene unit at 1,4- and 5,8- simultaneously. The kind of polynaphthalene possesses high densities of both phenanthrene-edge carbon and edge carbon, which could be expected a higher Li doping capacity. Together with the strong blue fluorescence emitting characteristics and high thermal stability, the polymer reveals the promising future in fields of electrode material for Li-ion rechargeable battery, polymer light-emitting diode and high-temperature-resistant materials.

Contents
1 Introduction
2 Synthesis of polynaphthalene
2.1 Oxidative polycondensation of naphthalene by Lewis acid catalysts
2.2 Dehalogenation polycondensation of dihalogenated naphthalene catalysed by sodium
2.3 Grignard metathesis catalysed by Ni(Ⅱ)-complex
2.4 Plasma polymerization
2.5 Yamamoto and Suzuki polymerizations
3 Performance of polynaphthalene
3.1 High thermal stability of polynaphthalene
3.2 Fluorescence of polynaphthalene
4 Application of polynaphthalene
4.1 Polynaphthalene light-emitting diode
4.2 Polynaphthalene Li-ion rechargeable battery
5 Outlook

CLC Number: 

[ 1 ]  Yamamoto T, Koizumi T1 Polymer, 2007, 48 ( 19 ) :5449—5472
[ 2 ]  Bargon J, Mohmand S, Waltman R J. J. Res. Develop. , 1983,27 (4) : 330—341
[ 3 ]  Nêll G, Lambert C, LynchM, et al. J. Phys. Chem. C, 2008,112 (6) : 2156—2164
[ 4 ]  Dias J R. J. Phys. Org. Chem. , 2007, 20: 395—409
[ 5 ]  Kovacic P, Wu C. J. Polym. Sci. , 1960, 47: 45—54
[ 6 ]  Kovacic P, Koch FW. J. Org. Chem. , 1963, 28 (7) : 1864—1867
[ 7 ]  Kovacic P, Lange R M. J. Org. Chem. , 1963, 28 ( 4 ) :968—972
[ 8 ]  Kovacic P, KyriakisA. J. Am. Chem. Soc. , 1963, 85: 454—458
[ 9 ]  Kovacic P, Oziomek J. J. Org. Chem. , 1964, 29 ( 1 ) :100—104
[ 10 ]  Kovacic P, Koch FW. J. Org. Chem. , 1965, 30: 3176—3181
[ 11 ]  Hara S, Toshima N. J. Electroanal. Chem. , 1994, 379:181—190
[ 12 ]  Huang ZM, Qu L T, Shi G Q, et al. J. Electroanal. Chem. ,2003, 556: 159—165
[ 13 ]  Hara S, Toshima N. Chem. Lett. , 1990, 19: 269—272
[ 14 ]  Zhang L J, Wan M X, Wen Y. Macromol. Rap id Commun. ,2006, 27 (5) : 366—371
[ 15 ]  BardeW S, Pakade S V, Yawale S P. J. Non-Cryst. Solids,2007, 353 (13 /15) : 1460—1465
[ 16 ]  Karim M R, Lee C J, LeeM S. J. Polym. Sci. PartA: Polym.Chem. , 2006, 44 (18) : 5283—5290
[ 17 ]  Li X G, Li J, HuangM R. Chem. Eur. J. , 2009, 15: 6446—6455
[ 18 ]  Hsing C F, Jones M B, Kovacic P. J. Polym. Sci. Part A:Polym. Chem. , 1981, 19: 973—984.
[ 19 ]  Arnautov S A, Kobryanskii V M. Macromol. Chem. Phys. ,2000, 201: 809—814
[ 20 ]  李新贵(Li X G) , 黄美荣(HuangM R) , 廖耀祖(Liao Y Z) .CN101328255, 2009
[ 21 ]  Erwin H, Wharton N J. US3431221, 1969
[ 22 ]  SatoM A, Kaeriyama K, Someno K. Makromol. Chem. , 1983,184: 2241—2249
[ 23 ]  Shi G Q, Xue G, Li C, et al. Polym. Bull. , 1994, 33: 325—329
[ 24 ]  Zecchin S, Tomat R, Schiavon G, et al. Synth. Met. , 1988,25: 393—399
[ 25 ]  马於光(Ma Y G) , 唐建国( Tang J G) , 张海峰( Zhang H F)等. 高等学校化学学报(Chem. J. Chin. Univ. ) , 1994, 15:1095—1096
[ 26 ]  Mori T, KijimaM. Op t. Mater. , 2007, 30 (4) : 545—552
[ 27 ]  Mori T, Kijima M. J. Polym. Sci. Part A: Polym. Chem. ,2008, 46: 4258—4263
[ 28 ]  Zhang J X, Liu C, Shi G Q, et al. J. Polym. Sci. Part B:Polym. Phys. , 2005, 43: 241—251
[ 29 ]  祖革( Zu G) , 罗维克(LuoW K) , 吴浩青(Wu H Q) . 化学学报(Acta Chimica Sinica) , 1999, 57: 465—471
[ 30 ]  Nishio S, Fukumura H, Tamura K, et al. J. Laser App l. ,2003, 15 (3) : 179—183
[ 31 ]  Yamabe T, Yata S, Wang S. Synth. Met. , 2003, 137:949—951
[ 32 ]  Wang S, Yata S, Nagano J, et al. J. Electrochem. Soc. , 2000,147 (7) : 2498—2502
[ 33 ]  Yata S, Hata Y, Kinoshita H, et al. Synth. Met. , 1995, 73:273—277

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