Electrosynthesis of highly conducting poly(1,5-dihydroxynaphthalene) in BF3·Et2O

European Polymer Journal

Volumn 45, Issue 8, 2009, Pages 2279-2287

  Lu, Baoyang ^a   Zeng, Liqiang ^a,b   Xu, Jingkun ^a   Le, Zhanggao ^b   Rao, Huoyu ^b  

^a Nanchang Normal University   (China)

^b EAST CHINA UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

Boron trifluoride diethyl etherate; Conducting polymers; Electrochemical polymerization; Fluorescence properties; Poly(1,5 dihydroxynaphthalene)

Indexed keywords

BLUE LIGHT; BORON TRIFLUORIDE DIETHYL ETHERATE; CHEMICAL METHOD; DIHYDROXYNAPHTHALENE; ELECTRICAL CONDUCTIVITY; ELECTRICAL TESTS; ELECTROCHEMICAL POLYMERIZATION; ELECTROCHROMIC PROPERTIES; FLUORESCENCE PROPERTIES; FLUORESCENCE QUANTUM YIELD; FTIR; HIGH QUALITY; OXIDATION POTENTIALS; POLY(1,5-DIHYDROXYNAPHTHALENE); QUANTUM CHEMISTRY CALCULATIONS; REDOX ACTIVITY; SPECTRAL STUDIES; STRUCTURAL CHARACTERIZATION; TETRABUTYLAMMONIUM TETRAFLUOROBORATE; THERMAL ANALYSIS; THERMAL STABILITY;

ACETONITRILE; ANODIC OXIDATION; CHEMICAL STABILITY; CONDUCTIVE PLASTICS; ELECTRIC CONDUCTIVITY; ELECTROCHEMICAL PROPERTIES; FLUORESCENCE; FOURIER TRANSFORM INFRARED SPECTROSCOPY; NAPHTHALENE; ORGANIC CONDUCTORS; POLYMERIZATION; REDOX REACTIONS; SEMICONDUCTING BORON; SPECTROSCOPIC ANALYSIS; STAINLESS STEEL; STEEL SHEET; THERMOANALYSIS;

CONDUCTING POLYMERS;

EID: 67650391359     PISSN: 00143057     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.eurpolymj.2009.05.005     Document Type: Article

References (43)

1. Ahuja T., Mir I.A., Kumar D., and Rajesh. Biomolecular immobilization on conducting polymers for biosensing applications. Biomaterials 28 (2007) 791-805
2. Wolf M.O. Recent advances in conjugated transition metal-containing polymers and materials. J Inorg Organomet Polym Mater 16 (2006) 189-199
3. Mortimer R.J., Dyer A.L., and Reynolds J.R. Electrochromic organic and polymeric materials for display applications. Displays 27 (2006) 2-18
4. Groenendaal L., Zotti G., Aubert P.H., Waybright S.M., and Reynolds J.R. Electrochemistry of poly(3,4-alkylenedioxythiophene) derivatives. Adv Mater 15 (2003) 855-879
5. Cosnier S. Biosensors based on electropolymerized films: new trends. Anal Bioanal Chem 377 (2003) 507-520
6. Tasch S., Grapner W., Leising G., Pu L., Wagaman M.P., and Grubbs R.H. Red-orange electroluminescence with new soluble and air-stable poly(naphthalene-vinylene)s. Adv Mater 7 (1995) 903-906
7. Susumu Hara, Naoki Toshima. Electrochemical polymerization of naphthalene using a composite electrolyte of aluminum chloride and copper(I) chloride. Chem Lett 1990;19:269-73.
8. Murakami M. Structural-properties of graphitized polyperinaphthalene fiber. J Appl Phys 67 (1990) 194-199
9. Hara S., and Toshima N. Electrochemical polymerization of aromatic-hydrocarbons on an ITO electrode using a composite electrolyte of aluminum-chloride and copper(I) chloride. J Electroanal Chem 379 (1994) 181-190
10. Huang M.R., Li X.G., and Li S.X. The synthesis of polydiaminonaphthalene and its highly reactive adsorption for heavy metal ions. Prog Chem 17 (2005) 299-309
11. Huang Z.M., Qu L.T., Shi G.Q., Chen F., and Hong X.Y. Electrochemical polymerization of naphthalene in the mixed electrolyte of boron trifluoride diethyl etherate containing trifluoroacetic acid and polyethylene glycol oligomer. J Electroanal Chem 556 (2003) 159-165
12. Zecchin S., Tomat R., Schiavon G., and Zotti G. Polynaphthalene films from anodic coupling of naphthalene. Synth Met 25 (1988) 393-399
13. Mori T., and Kijima M. Synthesis and optical properties of polynaphthalene derivatives. Opt Mater 30 (2007) 545-552
14. Won M.S., Yoon W.H., and Shim Y.B. Determination of selenium with a poly(1,8-diamino-naphthalene)-modified electrode. Electroanalysis 17 (2005) 1952-1958
15. Li X.G., Huang M.R., and Li S.X. Facile synthesis of poly(1,8-diaminonaphthalene) microparticles with a very high silver-ion adsorbability by a chemical oxidative polymerization. Acta Mater 52 (2004) 5363-5374
16. Nasalska A., and Skompska M. Removal of toxic chromate ions by the films of poly(1,8-diaminonaphthalene). J Appl Electrochem 33 (2003) 113-119
17. Shim Y.B., and Park J.H. Humidity sensor using chemically synthesized poly(1,5-diaminonaphthalene) doped with carbon. J Electrochem Soc 147 (2000) 381-385
18. Palys B.J., Skompska M., and Jackowska K. Sensitivity of poly 1,8-diaminonaphthalene to heavy metal ions-electrochemical and vibrational spectra studies. J Electroanal Chem 433 (1997) 41-48
19. Yamaguchi I., and Yamamoto T. Enzymatic polymerization to give poly(dihydroxynaphthalene)s and their photoluminescent aluminum complexes. React Funct Polym 61 (2004) 43-52
20. Shi G.Q., Jin S., Xue G., and Li C. A conducting polymer film stronger than aluminum. Science 267 (1995) 994-996
21. Li C., Shi G.Q., Liang Y.Q., Ye W., and Sha Z.L. High-quality poly(p-phenylene) film prepared by electrochemical polymerization of benzene at a stainless steel electrode. Polymer 38 (1997) 5023-5026
22. Xu J.K., Nie G.M., Zhang S.S., Han X.J., Hou J., and Pu S.Z. Electrosyntheses of freestanding polyindole films in boron trifluoride diethyl etherate. J Polym Sci Polym Chem 43 (2005) 1444-1453
23. Nie G.M., Xu J.K., Zhang S.S., and Han X.J. Electrodeposition of high-quality polycarbazole films in composite electrolytes of boron trifluoride diethyl etherate and ethyl ether. J Appl Electrochem 36 (2006) 937-944
24. Lu B.Y., Xu J.K., Fan C.L., Jiang F.X., and Miao H.M. Facile electrosynthesis of nitro-group-substituted oligopyrene with bicolored emission. Electrochim Acta 54 (2008) 334-340
25. Lu B.Y., Zeng L.Q., Xu J.K., Nie G.M., and Cai T. Electrochemical polymerization of 9,10-dihydrophenanthrene in boron trifluoride diethyl etherate containing concentrated sulfuric acid. Acta Chim Sin 66 13 (2008) 1593-1598
26. Lu B.Y., Xu J.K., Fan C.L., Miao H.M., and Shen L. Electrochemical polymerization of benzanthrone and characterization of its excellent green-light-emitting polymer. J Phys Chem B 113 (2009) 37-48
27. Huang Z.M., Shi G.Q., Qu L.T., and Hong X.Y. Electrochemical polymerization of β-naphthalene sulfonic acid in the mixed electrolyte of boron trifluoride diethyl etherate and trifluoroacetic acid. J Electroanal Chem 544 (2003) 41-46
28. Zimmermann C., Mohr M., Zipse H., Eichberger R., and Schnabel W. Photoionization of anthracene and anthracene derivatives. J Photochem Photobiol A Chem 125 (1999) 47-56
29. Tasi F.C., Chang C.C., Liu C.L., Chen W.C., and Jenekhe S.A. New thiophene-linked conjugated poly(azomethine)s: theoretical electronic structure, synthesis, and properties. Macromolecules 38 (2005) 1958-1966
30. Xu J.K., Shi G.Q., Qu L.T., and Zhang J.X. Electrosynthesis of high quality polypyrrole films in isopropyl alcohol solution of boron trifluoride diethyl etherate. Synth Met 135-6 (2003) 221-222
31. Otero T.F., and Larreta-Azelain E.D. Eelctrochemical generation of polythiophene films on platinum electrodes. Polymer 29 (1988) 1522-1526
32. Sonmez G., Schwendeman I., Schottland P., Zong K., and Reynolds J.R. N-substituted poly(3,4-propylenedioxypyrrole)s: high gap and low redox potential switching electroactive and electrochromic polymers. Macromolecules 36 (2003) 639-647
33. Choi K.M., Kim C.Y., and Kim K.H. Polymerization mechanism and physicochemical properties of electrochemically prepared polyindole tetrafluoroborate. J Phys Chem 96 (1992) 3782-3788
34. Zotti G., Zechin S., and Schiavon G. Structure of polyindoles from anodic coupling of indoles: an electrochemical approach. Chem Mater 6 (1994) 1742-1748
35. Talbi H., Humbert B., and Billaud D. FTIR and raman spectroscopic investigations on the redox behaviour of poly(5-cyanoindole) in acidic aqueous solutions. Spectrochim Acta A 54 (1998) 1879-1893
36. Hoffmann R., and Woodward R.B. Orbital symmetries and endo-exo relationships in concerted cycloaddition reactions. J Am Chem Soc 87 (1965) 4388-4389
37. Hoffmann R., and Woodward R.B. The conservation of orbital symmetry. Acc Chem Res 1 (1967) 17-22
38. Fukui K. Recognition of stereochemical paths by orbital interaction. Acc Chem Res 4 (1971) 57-64
39. Fukui K. The path of chemical reactions: the IRC approach. Acc Chem Res 14 (1981) 363-368
40. Smith J.R., Cox P.A., and Campbell S.A. Application of density functional theory in the synthesis of electroactive polymers. J Chem Soc Faraday Trans 91 (1995) 2331-2338
41. Ando S., and Ueda M. Density functional theory calculations of the local spin densities of 3-substituted thiophenes and the oligomerization mechanism of 3-methylsulfanyl thiophene. Synth Met 129 (2002) 207-213
42. Doskocz J., Doskocz M., Roszak S., Soloducho J., and Leszczynski J. Theoretical studies of symmetric five-membered heterocycle derivatives of carbazole and fluorene: precursors of conducting polymers. J Phys Chem A 110 (2006) 13989-13994
43. Thieblemont J.C., Brun A., Marty J., and Planche M.F. Thermal analysis of polypyrrole oxidation in air. Polymer 36 (1995) 1605-1610