Thiophene-based ionic liquids: Synthesis, physical properties, self-assembly, and oxidative polymerization

Polymers for Advanced Technologies

Volumn 19, Issue 10, 2008, Pages 1369-1382

  Burns, Christopher T ^a   Lee, Sungwon ^a   Seifert, Sönke ^a   Firestone, Millicent A ^a  

^a ARGONNE NATIONAL LABORATORY   (United States)

Author keywords

Ionic liquids; Polythiophene; SAXS; Self assembly

Indexed keywords

ABSORPTION SPECTROSCOPY; BINARY MIXTURES; CHEMICAL REACTIONS; CONFORMATIONS; DOPING (ADDITIVES); ELECTRIC LOAD MANAGEMENT; IONIZATION OF LIQUIDS; IONS; LIQUIDS; MONOMERS; OPTICAL MICROSCOPY; PHOTORESISTS; POLYMERIZATION; POLYMERS; SCATTERING; SELF ASSEMBLY; SULFUR COMPOUNDS; THIOPHENE; WATER CONTENT; X RAY SCATTERING;

ALKYL CHAINS; AMPHIPHILIC; CHEMICAL DOPING; COLUMNAR MESOPHASES; CONFORMATIONAL STATES; COUNTER ANIONS; DILUTE AQUEOUS SOLUTIONS; ELECTROCHEMICAL STUDIES; ELECTRONIC ABSORPTION SPECTROSCOPIES; LESSER EXTENTS; LIQUID CRYSTALLINE MESOPHASES; LONG-RANGE ORDERINGS; LOW WATER CONTENTS; NITRATE SALTS; OXIDATION POTENTIALS; OXIDATIVE COUPLINGS; OXIDATIVE POLYMERIZATIONS; POLARIZED OPTICAL MICROSCOPIES; POLYMER CONFORMATIONS; POLYTHIOPHENE; SAXS; WATER-SOLUBLE POLYMERS;

IONIC LIQUIDS;

MONOMER; OXIDATION; PHYSICAL PROPERTY; POLYMERIZATION; SYNTHESIS;

EID: 58049218669     PISSN: 10427147     EISSN: 10991581     Source Type: Journal    
DOI: 10.1002/pat.1200     Document Type: Conference Paper

References (55)

1. Roncali J. Conjugated poly(thiophenes) - synthesis, functionalization, and applications. Chem. Rev. 1992; 92: 711-738.
2. Higgins SJ. Conjugated polymers incorporating pendant functional groups - synthesis and characterisation. Chem. Soc. Rev. 1997; 26: 247-257.
3. McCullough RD. The chemistry of conducting polythiophenes. Adv. Mater. 1998; 10: 93-94.
4. Rutherford DR, Stille JK, Elliott CM, Reichert VR. Poly(2,5-ethynylenethiophenediylethynylenes), related heteroaromatic analogs, and poly(thieno[3,2-B]thiophenes) - synthesis and thermal and electrical-properties. Macromolecules 1992; 25: 2294-2306.
5. Patil AO, Ikenoue Y, Wudl F, Heeger AJ. Water-soluble conducting polymers. J. Am. Chem. Soc. 1987; 109: 1858-1859.
6. Ikenoue Y, Chiang J, Patil AO, Wudl F, Heeger AJ. Verification of the cation-popping doping mechanism of self-doped polymers. J. Am. Chem. Soc. 1988; 110: 2983-2985.
7. Ikenoue Y, Saida Y, Kira M, Tomozawa H, Yashima H, Kobayashi MA. Facile preparation of a self-doped conducting polymer. J. Chem. Soc. Chem. Commun. 1990; 23: 1694-1695.
8. Chen S-A, Hau M-Y. Compatibilities and electrostatic interactions in the blends of self-acid-doped conjugated conducting polymer, poly[2-(3′-thienyl)ethanesulfonic], acid and its sodium salt with poly{vinyl alcohol). Macromolecules 1996; 29: 4919-4925.
9. Chayer M, Faid K, Leclerc M. Highly conducting water-soluble polythiophene derivatives. Chem. Mater. 1997; 9: 2902-2905.
10. Groenendaal LB, Jonas F, Freitag D, Pielartzik H, Reynolds JR. Poly(3,4-ethylenedioxythiophene) and its derivatives: past, present, and future. Adv. Mater. 2000; 12: 481-494.
11. Batra D, Seifert S, Varela LM, Liu ACY, Firestone MA. Solvent-mediated plasmon tuning in a gold-nanoparticlepoly(ionic liquid) composite. Adv. Funct. Mater. 2007; 17: 1279-1287.
12. Batra D, Hay DNT, Firestone MA. Formation of a biomimetic, liquid-crystalline hydrogel by self-assembly and polymerization of an ionic liquid. Chem. Mater. 2007; 19: 4423-4431.
13. McCullough RD, Ewbank PC, Loewe RS. Self-assembly and disassembly of regioregular water soluble polythiophenes: chemoselective ionchromatic sensing in water. J. Am. Chem. Soc. 1997; 119: 633-634.
14. Naudin E, Ho HA, Bonin MA, Breau L, Belanger D. Preparation and characterization of poly 2,3-dimethyl-1-(4-thien-3-ylbenzyl)-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl) imide. Macromolecules 2002; 35: 4983-4987.
15. Ho HA, Leclerc M. New colorimetric and fluorometric chemosensor based on a cationic polythiophene derivative for iodide-specific detection. J. Am. Chem. Soc. 2003; 125: 4412-4413.
16. Viinikanoja A, Areva S, Kocharova N, Aaritalo T, Vuorinen M, Savunen A, Kankare J, Lukkari J. Structure of self-assembled multilayers prepared from water-soluble polythiophenes. Langmuir 2006; 22: 6078-6086.
17. Ho HA, Boissinot M, Bergeron MG, Corbeil G, Dore K, Boudreau D, Leclerc M. Colorimetric and fluorometric detection of nucleic acids using cationic polythiophene derivatives. Angew. Chem. Intl. Ed. 2002; 41: 1548-1551.
18. Ho HA, Leclerc M. Optical sensors based on hybrid aptamer/conjugated polymer complexes. J. Am. Chem. Soc. 2004; 126: 1384-1387.
19. Ho HA, Bera-Aberem M, Leclerc M. Optical sensors based on hybrid DNA/ conjugated polymer complexes. Chem. Eur. J. 2005; 11: 1718-1724.
20. Dore K, Dubus S, Ho HA, Levesque I, Brunette M, Corbeil G, Boissinot M, Boivin G, Bergeron MG, Boudreau D, Leclerc M. Fluorescent polymeric transducer for the rapid, simple, and specific detection of nucleic acids at the zeptomole level. J. Am. Chem. Soc. 2004; 126: 4240-4244.
21. Mukai T, Yoshio M, Kato T, Yoshizawa M, Ohno H. Anisotropic ion conduction in a unique smectic phase of self-assembled amphiphilic ionic liquids. Chem. Commun. 2005; 10: 1333-1335.
22. Binnemans K. Ionic liquid crystals. Chem. Rev. 2005; 105: 4148-4204.
23. Firestone MA, Dzielawa JA, Zapol P, Curtiss LA, Seifert S, Dietz ML. Lyotropic liquid-crystalline gel formation in a room-temperature ionic liquid. Langmuir 2002; 18: 7258-7260.
24. Batra D, Seifert S, Firestone MA. The effect of cation structure on the mesophase architecture of self-assembled and polymerized imidazolium-based ionic liquids. Macromol. Chem. Phys. 2007; 208: 1416-1427.
25. Firestone MA, Rickert PG, Seifert S, Dietz ML. Anion effects on ionogel formation in N,N0-dialkylimidazolium-based ionic liquids. Inorg. Chim. Acta 2004; 357: 3991-3998.
26. 1H-imidazolium tetrafluoroborate. Helv. Chim. Acta 2004; 87: 2556-2565.
27. Bauerle P, Wurthner F, Heid S. Thiophenes 1. Facile synthesis of 3-(omega-haloalkyl)thiophenes as key building-blocks for functionalized thiophenes and polythiophenes. Angew. Chem. Intl. Ed. 1990; 29: 419-420.
28. Chaloner PA, Gunatunga SR, Hitchcock PB. Synthesis of substituted oligothiophenes and x-ray crystal structures of 30-methyl-2,2′:5′,2″-terthiophene, 3,3″-dimethyl-2,2′:5′,2″-terthiophene and 5′-(2-thienyl)-2,2′:3′,2″-terthiophene. J. Chem. Soc. Perkin Trans. 1997; 2: 1597-1604.
29. Firestone MA, Shank ML, Sligar SG, Bohn PW. Film architecture in biomolecular assemblies. Effect of linker on the orientation of genetically engineered surface-bound proteins. J. Am. Chem. Soc. 1996; 118: 9033-9041.
30. Cirpan A, Alkan S, Toppare L, Cianga I, Yagci Y. Synthesis and characterization of conducting copolymers of thiophene-3-yl acetic acid cholesteryl ester with pyrrole. J. Mater. Sci. 2002; 37: 1767-1775.
31. Rickert PG, Antonio MR, Firestone MA, Kubatko KA, Szreder T, Wishart JF, Dietz ML. Tetraalkylphosphonium polyoxometalates: electroactive, "task-specific" ionic liquids. Dalton Trans. 2007; 5: 529-531.
32. Rickert PG, Antonio MP, Firestone MA, Kubatko KA, Szreder T, Wishart JF, Dietz ML. Tetraalkylphosphonium polyoxometalate ionic liquids: electroactive, thermallystable "liquid POMS". J. Phys. Chem. B 2007; 111: 4685-4692.
33. Earle MJ, Gordon CM, Plechkova NV, Seddon KR, Welton T. Decolorization of ionic liquids for spectroscopy. Anal. Chem. 2007; 79: 758-764.
34. Irvin DJ, Reynolds JR. Tuning the band gap of easily oxidized bis(2-thienyl)- and bis(2-(3,4-ethylenedioxythiophene))-phenylene polymers. Polym. Adv. Technol. 1998; 9: 260-265.
35. 4. J. Appl. Polym. Sci. 2000; 77: 312-322.
36. Grenier CRG, Pisula W, Joncheray TJ, Mullen K, Reynolds JR. Regiosymmetric poly (dialkylphenylenedioxythio-Thiophene-based ILs 1381 phene)s: electron-rich, stackable pi-conjugated nanoribbons. Angew. Chem. Intl. Ed. 2007; 46: 714-717.
37. Thunemann AF, Ruppelt D, Burger C, Mullen K. Long-range ordered columns of a hexabenzo[bc,ef,hi,kl,no,qr]coronenepolysiloxane complex: towards molecular nanowires. J. Mater. Chem. 2000; 10: 1325-1329.
38. Lemaire BJ, Davidson P, Ferre J, Jamet JP, Petermann D, Panine P, Dozov I, Stoenescu D, Jolivet JP. The complex phase behaviour of suspensions of goethite (alpha-FeOOH) nanorods in a magnetic field. Faraday Discuss. 2005; 128: 271-283.
39. Seo K, Kim S, Gihm SH, Park CR, Park SY. Highly florescent columnar liquid crystals with elliptical molecular shape: oblique molecular stacking and excited-state intramolecular proton-transfer. J. Mater. Chem. 2007; 17: 5052-5057.
40. Diaz-Quijada GA, Pinto BM, Holdcroft S. Regiochemical analysis of water soluble conductive polymers: sodium poly(omega-(3-thienyl)alkanesulfonates). Macromolecules 1996; 29: 5416-5421.
41. Qiao XY, Wang XH, Mo ZS. The effects of different alkyl substitution on the structures and properties of poly(3-alkylthiophenes). Synth. Met. 2001; 118: 89-95.
42. Bhat K, Kumar MS. N and p doped poly(3,4-ethylenedioxythiophene) electrode materials for symmetric redox supercapacitors. J. Mater. Sci. 2007; 42: 8158-8162.
43. Mohammad F. Compensation behaviour of electrically conductive polythiophene and polypyrrole. J. Phys. D: Appl. Phys. 1998; 31: 951-959.
44. Yamamoto T, Abla M. Synthesis of non-doped poly(3,4-ethylenedioxythiophene) and its spectroscopic data. Synth. Met. 1999; 100: 237-239.
45. Colthup NB, Daly LH, Wiberley SE. Introduction to Infrared and Raman Spectroscopy (3rd edn). Academic Press, Inc.: New York, 1990.
46. Lucht B, Euler W, Gregory OJ. Investigation of the thermochromic properties of polythiophenes in host polymers. Polym. Prep. 2002; 43: 59-60.
47. Zhang SY, Kong F, Sun R, Yuan RK, Jiang XQ, Yang CZ. Synthesis, characterization, and electro-optical properties of a soluble conjugated polymer containing an oxadiazole unit in the main chain. J. Appl. Polym. Sci. 2003; 89: 2618-2623.
48. 3 polymer composite-super-paramagnetic behavior and variable range hopping 1D conduction mechanism-synthesis and characterization. Polym. Adv. Technol. 2008; 19(3): 229-236.
49. Touillon G, Garnier F. Electrochemical doping of polythiophene in aqueous medium. J. Electroanal. Chem. 1984; 161: 407-414.
50. Ding AL, Pei J, Lai Y-H, Haung W. Phenylene-functionalized polythiophene derivatives for light-emitting diodes: their synthesis, characterization and properties. J. Mater. Chem. 2001; 11: 3082-3086.
51. Pei J, Yu WL, Ni J, Lai Y-H, Haung W, Heeger AJ. Thiophene-based conjugated polymers for light-emitting diodes: effect of aryl groups on photoluminescence efficiency and redox behavior. Macromolecules 2001; 34: 7241-7248.
52. Soudan P, Lucas P, Ho HA, Jobin D, Breau L, Belanger D. Synthesis, chemical polymerization and electrochemical properties of low band gap conducting polymers for use in supercapacitors. J. Mater. Chem. 2001; 11: 773-782.
53. Meng H, Perepichka DF, Bendikov M, Wudl F, Pan GZ, Yu WL, Dong WL, Brown S. Solid-state synthesis of a conducting polythiophene via an unprecedented heterocyclic coupling reaction. J. Am. Chem. Soc. 2003; 125(49): 15153-15162.
54. Arroyovillan MI, Diazquijada GA, Abdou MSA, Holdcroft S. Poly(N-(3-thienyl)alkanesulfonates) - synthesis, regioregularity, morphology, and photochemistry. Macromolecules 1995; 28: 975-984.
55. Firestone MA, Williams DE, Seifert S, Csencsits R. Nanoparticle arrays formed by spatial compartmentalization in a complex fluid. Nano Lett. 2001; 1: 129-135.