Abstract
A series of 3-(p-X-phenyl) thiophene monomers (X= –H, –CH3, –OCH3, –COCH3, –COOC2H5, –NO2) was electrochemically polymerized to furnish polymer films that could be reversibly reduced and oxidized (n- and p-doped). The oxidation potentials of the monomers and formal potentials of the n- and p-doping processes of polymers were correlated with resonance and inductive effects of the substituents on the phenyl ring as well as the semiempirically calculated heat of formation of the monomer radical cations.
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Santhanam KSV, Gupta N (1993) TRIP 1:284
Panero S, Passerini S, Scrosati B (1993) Mol Cryst Liq Cryst 229:97
Huang SC, Huang SM, Ng H, Kaner RB (1993) Synth Met 55–57:4047
Baughman RH (1991) Makromol Chem Macromol Symp 51:193
Conway BE (1991) Electrochem Soc 138:1539
Mastragostino M, Arbizzani C, Bongini A, Barbarella G, Zambianchi M (1993) Electrochim Acta 38:135
Posudievskii OY, Konoshchuk NV, Il’in VG, Pokhodenko VD (2002) Theor Exp Chem 38:283
Xu Y, Loveday DC, Ferraris JP, Smith DW Jr (1998) Polymer Reprints 39:143
Heinze J (1990) Top Curr Chem 152:1
Chandler GK, Pletcher D (1985) Electrochemistry 10:117
Diaz AF, Castillo JI, Logan JA, Lee W-Y (1981) J Electroanal Chem 129:115
Otero TF, Tejada R, Elola AS (1987) Polymer 28:651
Street GB, Clarke TC, Geiss RH, Lee VY, Nazzal A, Pfluger P, Scott JC (1983) J Phys C 3(44):599
Gottesfeld S, Redondo A, Feldberg SW (1987) J Electrochem Soc 134:271
Kalaji M, Peter LM, Abrantes LM, Mesquita JC (1989) J Electroanal Chem 274:289
Sato M, Tanaka S, Kaeriyama K(1987) J Chem Soc, Chem Commun 1725
Sato M, Tanaka S, Kaeriyama K (1989) Makromol Chem 190:1233
Onoda M, Nakayama H, Morita S, Yashino K (1993) Synth Met 55–57:275
Guerrero DJ, Ren X, Ferraris JP (1994) Chem Mater 6:1437
Rieke RD, Kim S-H, Wu X (1997) J Org Chem 62:6921
Gritzner G, Kuta J (1984) Pure Appl Chem 56:461
Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Zakrzewski VG, Montgomery JA Jr, Stratmann RE, Burant JC, Dapprich S, Millam JM, Daniels AD, Kudin KN, Strain MC, Farkas O, Tomasi J, Barone V, Cossi M, Cammi R, Mennucci B, Pomelli C, Adamo C, Clifford S, Ochterski J, Petersson GA, Ayala PY, Cui Q, Morokuma K, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Cioslowski J, Ortiz JV, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Gomperts R, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Gonzalez C, Challacombe M, Gill MWP, Johnson B, Chen W, Wong MW, Andres JL, Gonzalez C, Head-Gordon M, Replogle ES, Pople JA (1998) Gaussian 98, Revision A.3. Gaussian Inc., Pittsburgh
Dewar M, Thiel W (1977) J Am Chem Soc 99:4499
Marque P, Roncali J, Garnier F (1987) J Electroanal Chem 218:107
Ue M, Ida K, Mori S (1994) J Electrochem Soc 141:2989
Barthel J, Gores HJ, Schmeer G, Wechter R (1983) Top Curr Chem 111:33
Ferraris JP, Eissa MM, Brotherston ID, Loveday DC, Moxey AA (1998) J Electroanal Chem 459:57
Rudge A, Raistrick I, Gottesfeld S, Ferraris JF (1994) Electrochim Acta 39:273
Borjas R, Buttry DA (1991) Chem Mater 3:872
Mastragostino M and Soddn L (1990) Electrochim Acta 35:463
Pokhodenko VD, Krylov VA (1991) Synth Met 41–43:533
Roncali J (1992) Chem Rev 92:711
Ambrose JF, Nelson RF (1968) J Electrochem Soc 92:1161
Adams RN (1969) Acc Chem Res 2:175
Dian G, Barbey G, Decroix B (1986) Synth Met 13:281
March J (1992) Advanced organic chemistry 4th edn. Wiley, New York, pp 280ff
Gofer Y, Killian JG, Sarker H, Pochler TO, Searson PC (1998) J Electroanal Chem 413:103
Wahman RJ, Bargon J, Diaz AF (1983) J Phys Chem 87:1459
Wahman RJ, Diaz AF, Bargon J (1984) J Phys Chem 88:4343
Sarker H, Gofer Y, Killian JG, Pohler TO, Searson PC (1997) Synth Met 88:179
Kinbara E, Kunugi Y, Harima Y, Yamashita K (2000) Synth Met 114:295
Roncali J (1997) Chem Rev 97:173
Chung C-C, Kaufman JH, Heeger AJ, Wudl F (1985) Mol Cryst Liq Cryst 118:205
March J (1992) Advanced organic chemistry 4th edn. Wiley, New York, pp 242–250
Carey FA, Sundberg RJ (1993) Advanced organic chemistry 3rd edn. Plenum, New York, pp 196–210
Zuman P (1967) Substituent effects in organic polarography. Plenum, New York
Abruna HD, Denisevich P, Umana M, Meyer TJ, Murray RW (1981) J Am Chem Soc 103:1
Acknowledgments
Financial support from the fonds of the Chemische Industrie and the Deutsche Forschungsgemeinschaft (Graduiertenkolleg GRK 829/1) is gratefully acknowledged.. We are grateful to K. Banert for helpful discussions and support in synthesis of the monomers. Finally we thank H.-J. Schäfer for helpful discussions.
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Presented at the 4th Baltic Conference on Electrochemistry, Greifswald, March 13-16, 2005
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Alhalasah, W., Holze, R. Electrochemical materials science: tailoring intrinsically conducting polymers. The example: substituted thiophenes. J Solid State Electrochem 9, 836–844 (2005). https://doi.org/10.1007/s10008-005-0024-8
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DOI: https://doi.org/10.1007/s10008-005-0024-8