Polythiophene-cellulose composites: Synthesis, optical properties and homogeneous oxidative co-polymerization

Holzforschung

Volumn 66, Issue 1, 2012, Pages 9-19

  Sakakibara, Keita ^a   Rosenau, Thomas ^a  

^a UNIVERSITY OF NATURAL RESOURCES AND LIFE SCIENCES   (Austria)

Author keywords

Cellulose; Cellulose composite; Co polymerization; Conductivity; Cross linking; Derivatization; Polythiophene; Regioselective functionalization

Indexed keywords

BROAD BANDS; CO-MONOMER; COMONOMERS; CONJUGATED STRUCTURES; CROSS-LINKED NETWORKS; DERIVATIZATIONS; ENVIRONMENTAL CONDITIONS; OLIGOTHIOPHENES; POLY-THIOPHENE; PROTECTING GROUP; REGIOSELECTIVE FUNCTIONALIZATION; SEMICONDUCTIVITY; SIDE-CHAINS; STACKING STRUCTURES; TERTHIOPHENES; UV-VIS ABSORPTION SPECTRA;

CELLULOSE; CELLULOSE DERIVATIVES; CIRCULAR DICHROISM SPECTROSCOPY; CONJUGATED POLYMERS; DICHROISM; ELECTRIC CONDUCTIVITY; FILM PREPARATION; MONOMERS; POLYMERIZATION; THIOPHENE; ULTRAVIOLET SPECTROSCOPY;

WOOD;

CELLULOSE DERIVATIVES; CIRCULAR DICHROISM; COMPOSITES; LIGNINS; MONOMERS; POLYMERS; RESISTIVITY; THIOPHENES;

EID: 84856180046     PISSN: 00183830     EISSN: 1437434X     Source Type: Journal    
DOI: 10.1515/HF.2011.137     Document Type: Article

References (50)

1. Aburatani, R., Okamoto, Y., Hatada, K. (1990) Optical resolving ability of 3,5-dimethylphenylcarbamates of oligosaccharides and cyclodextrins. Bull. Chem. Soc. Jpn. 63:3606-3610.
2. 3. Macromolecules 27:6503-6506.
3. Baek, M.-G., Stevens, R.C., Charych, D.H. (2000) Design and synthesis of novel glycopolythiophene assemblies for colorimetric detection of influenza virus and E. coli. Bioconjugate Chem. 11:777-788.
4. Bao, Z., Dodabalapur, A., Lovinger, A.J. (1996) Soluble and processable regioregular poly(3-hexylthiophene) for thin film fieldeffect transistor applications with high mobility. Appl. Phys. Lett. 69:4108-4110. (Pubitemid 126647952)
5. Bjerring, M., Nielsen, J.S., Nielsen, N.C., Krebs, F.C. (2007) Polythiophene by solution processing. Macromolecules 40:6012-6013. (Pubitemid 47280879)
6. Burroughes, J.H., Bradley, D.D.C., Brown, A.R., Marks, R.N., Mackay, K., Friend, R.H., Burns, P.L., Holmes, A.B. (1990) Light-emitting diodes based on conjugated polymers. Nature 347:539-541. (Pubitemid 120015057)
7. Gómez, J.A.C., Erler, U.W., Klemm, D.O. (1996) 4-Methoxy substituted trityl groups in 6-O protection of cellulose: homogeneous synthesis, characterization, detritylation. Macromol. Chem. Phys. 197:953-964. (Pubitemid 126464836)
8. Groenendaal, L.B., Jonas, F., Freitag, D., Pielartzik, H., Reynolds, J.R. (2000) Poly(3,4-ethylenedioxythiophene) and its derivatives: past, present, and future. Adv. Mater. 12:481-494.
9. Heeger, A.J. (2001) Semiconducting and metallic polymers: the fourth generation of polymeric materials (Nobel Lecture). Angew. Chem. Int. Ed. 40:2591-2611. (Pubitemid 32691691)
10. Henry, C.D., Tebbe, H., Wegner, G., Armand, F., Ruaudel-Teixier, A. (1997) Ultrathin cellulose ether network as a host matrix for alkylthiophene polymerization. Adv. Mater. 9:805-808. (Pubitemid 127532936)
11. Hu, Z., Reichmanis, E. (2011) Synthesis of electroactive polystyrene derivatives para-substituted with p-conjugated oligothiophene via postgrafting functionalization. J. Polym. Sci. Part A: Polym. Chem. 49:1155-1162.
12. Jang, S.-Y., Sotzing, G.A., Marquez, M. (2004) Poly(thiophene)s prepared via electrochemical solid-state oxidative cross-linking. A comparative study. Macromolecules 37:4351-4359.
13. Kern, H., Choi, S., Wenz, G., Heinrich, J., Ehrhardt, L., Mischnick, P., Garidel, P., Blume, A. (2000) Synthesis, control of substitution pattern and phase transitions of 2,3-di-O-methylcellulose. Carbohydr. Res. 326:67-79. (Pubitemid 30227377)
14. Klemm, D., Heublein, B., Fink, H.-P., Bohn, A. (2005) Cellulose: fascinating biopolymer and sustainable raw material. Angew. Chem. Int. Ed. 44:3358-3393. (Pubitemid 40793591)
15. Lange, U., Roznyatovskaya, N.V., Mirsky, V.M. (2008) Conducting polymers in chemical sensors and arrays. Anal. Chim. Acta 614:1-26.
16. Li, X., Chapple, C. (2010) Understanding lignification: challenges beyond monolignol biosynthesis. Plant Physiol. 154:449-452.
17. Li, X.-G., Li, J., Meng, Q.-K., Huang, M.-R. (2009) Interfacial synthesis and widely controllable conductivity of polythiophene microparticles. J. Phys. Chem. B 113:9718-9727.
18. Liang, Y., Feng, D., Wu, Y., Tsai, S.-T., Li, G., Ray, C., Yu, L. (2009) Highly efficient solar cell polymers developed via finetuning of structural and electronic properties. J. Am. Chem. Soc. 131:7792-7799.
19. MacDiarmid, A.G. (2001) Synthetic metals: a novel role for organic polymers (Nobel Lecture). Angew. Chem. Int. Ed. 40:2581-2590. (Pubitemid 32691690)
20. McCullough, R.D., Lowe, R.D., Jayaraman, M., Anderson, D.L. (1993) Design, synthesis, and control of conducting polymer architectures: structurally homogeneous poly(3-alkylthiophenes). J. Org. Chem. 58:904-912.
21. McQuade, D.T., Pullen, A.E., Swager, T.M. (2000) Conjugated polymer- based chemical sensors. Chem. Rev. 100:2537-2574.
22. MuCullough, R.D. (1998) The chemistry of conducting polythiophenes. Adv. Mater. 10:93-116.
23. Nishio, Y. (2006) Material functionalization of cellulose and related polysaccharides via diverse microcompositions. Adv. Polym. Sci. 205:97-151.
24. Njuguna, J., Pielichowski, K. (2004) Recent developments in polyurethane- based conducting composites. J. Mater. Sci. 39:4081-4094.
25. Oosterhout, S.D., Wienk, M.M., Van Bavel, S.S., Thiedmann, R., Jan Anton Koster, L., Gilot, J., Loos, J., Schmidt, V., Janssen, R.A.J. (2009) The effect of three-dimensional morphology on the efficiency of hybrid polymer solar cells. Nat. Mater. 8:818-824.
26. Park, S.H., Roy, A., Beaupré, S., Cho, S., Coates, N., Moon, J.S., Moses, D., Leclerc, M., Lee, K., Heeger, A.J. (2009) Bulk heterojunction solar cells with internal quantum efficiency approaching 100%. Nat. Photonics 3:297-303.
27. Png, R.-Q., Chia, P.-J., Tang, J.-C., Liu, B., Sivaramakrishnan, S., Zhou, M., Khong, S.-H., Chan, H.S.O., Burroughes, J.H., Chua, L.-L., Friend, R.H., Ho, P.K.H. (2010) High-performance polymer semiconducting heterostructure devices by nitrene-mediated photocrosslinking of alkyl side chains. Nat. Mater. 9:152-158.
28. Redl, F.X., Köthe, O., Röckl, K., Bauer, W., Daub, J. (2000) Azulene appended cellulose: synthesis, optical and chiroptical properties, film formation by electrochemical oxidation. Macromol. Chem. Phys. 201:2091-2100.
29. Redl, F.X., Lutz, M., Daub, J. (2001) Chemistry of porphyrinappended cellulose strands with a helical structure: spectroscopy, electrochemistry, and in situ circular dichroism spectroelectrochemistry. Chem. Eur. J. 7:5350-5358.
30. Sakakibara, K., Nakatsubo, F. (2008a) Effect of fullerene on photocurrent performance of 6-O-porphyrin-2,3-di-O-stearoylcellulose Langmuir-Blodgett films. Macromol. Chem. Phys. 209: 1274-1281.
31. Sakakibara, K., Nakatsubo, F. (2008b) Fabrication of anodic photocurrent generation systems by use of 6-O-dihydrophytylcellulose as a matrix or a scaffold of porphyrins. Cellulose 15:825-835.
32. Sakakibara, K., Nakatsubo, F. (2010) Effect of central metals in the porphyrin ring on photocurrent performance of cellulose Langmuir- Blodgett films. Macromol. Chem. Phys. 211:2429-2433.
33. Sakakibara, K., Ogawa, Y., Nakatsubo, F. (2007) First cellulose Langmuir-Blodgett films towards photocurrent generation systems. Macromol. Rapid Commun. 28:1270-1275. (Pubitemid 47252038)
34. Salmén, L., Burgert, I. (2009) Cell wall features with regard to mechanical performance. A review. Holzforschung 63:121-129.
35. Sarkanen, K.V. and Ludwig, C.H. (1971). Lignins-Occurence, Formation, Structure and Reactions. Wiley-Interscience, New York.
36. Schillinger, E.-K., Mena-Osteritz, E., Hentschel, J., Börner, H.G., Bäuerle, P. (2009) Olitothiophene versus b-sheet peptide: synthesis and self-assembly of an organic semiconductor-peptide hybrid. Adv. Mater. 21:1562-1567.
37. Shirakawa, H. (2001) The discovery of polyacetylene film: the dawning of an era of conducting polymers (Nobel Lecture). Angew. Chem. Int. Ed. 40:2574-2580.
38. Sirringhaus, H., Brown, P.J., Friend, R.H., Nielsen, M.M., Bechgaard, K., Langeveld-Voss, B.M.W., Spiering, A.J.H., Janssen, R.A.J., Meijer, E.W., Herwig, P., De Leeuw, D.M. (1999) Twodimensional charge transport in self-organized, high-mobility conjugated polymers. Nature 401:685-688.
39. Sirringhaus, H., Bird, M., Richards, T., Zhao, N. (2010) Charge transport physics of conjugated polymer field-effect transistors. Adv. Mater. 22:3893-3898.
40. Stevanic, J.S., Salmén, L. (2009) Orientation of the wood polymers in the cell wall of spruce wood fibres. Holzforschung 63: 497-503.
41. Thompson, B.C., Fréchet, J.M.J. (2008) Polymer-fullerene composite solar cells. Angew. Chem. Int. Ed. 47:58-77.
42. Wang, M., Zou, S., Guerin, G., Shen, L., Deng, K., Jones, M., Walker, G.C., Scholes, G.D., Winnik, M.A. (2008) A water-soluble pH-responsive molecular brush of poly(N,N-dimethylaminoethyl methacrylate) grafted polythiophene. Macromolecules 41:6993-7002.
43. Wegner, G. (2003) Nanocomposites of hairy-rod macromolecules: concepts, constructs, and materials. Macromol. Chem. Phys. 204:347-357.
44. Wu, Y., Seo, T., Maeda, S., Sasaki, T., Irie, S., Sakurai, K. (2005) Circular dichroism induced by the helical conformations of acetylated chitosan derivatives bearing cinnamate chromophores. J. Polym. Sci. Part A: Polym. Chem. 43:1354-1364. (Pubitemid 40860118)
45. Xue, C., Luo, F.-T., Liu, H. (2007) Post-polymerization functionalization approach for highly water-soluble well-defined regioregular head-to-tail glycopolythiophenes. Macromolecules 40: 6863-6870. (Pubitemid 47522667)
46. Yamamoto, T. (1992) Electrically conducting and thermally stable p-conjugated poly(arylene)s prepared by organometallic processes. Prog. Polym. Sci. 17:1153-1205.
47. Yang, X., Loos, J. (2007) Toward high-performance polymer solar cells: the importance of morphology control. Macromolecules 40:1353-1362. (Pubitemid 46423651)
48. Yassar, A., Moustrou, C., Youssoufi, H.K., Samat, A., Guglielmetti, R., Garnier, F. (1995) Synthesis and characterization of poly(thiophenes) functionalized by photochromic spironaphthoxazine groups. Macromolecules 28:4548-4553.
49. Yeh, C.-F., Chao, C.-H., Sung, K., Wang, L. (2008) Conducting polymer composite films with core-shell-like nanostructure prepared from terthiophene-terminated starburst poly(n-butyl acrylate). Macromolecules 41:6608-6611.
50. Zhao, Q., Wang, H., Yin, Y., Xu, Y., Chen, F., Dixon, R.A. (2010) Syringyl lignin biosynthesis is directly regulated by a secondary cell wall master switch. Proc. Natl. Acad. Sci. USA 107: 14496-14501.