29. Zen A, Pflaum J, Hirschmann S, Zhuang W, Jaiser F, Asawapirom U, Rabe JP, Scherf U,
Neher D (2004) Effect of molecular weight and annealing of poly(3-hexylthiophene)s on the
performance of organic field-effect transistors. Adv Funct Mater 14:757–764
30. Kline RJ, McGehee MD, Kadnikova EN, Liu J, Frechet JMJ, Toney MF (2005) Dependence
of regioregular poly(3-hexylthiophene) film morphology and field-effect mobility on molecular weight. Macromolecules 38:3312–3319
31. Meyer V (1883) Thiophene, a substance contained in coal-tar benzene. Chem Ber 16:1465–
1478
32. Meyer V (1884) The thiophene and pyrroline groups. Chem Ber 16:2968–2975
33. Meisel SL, Johnson GC, Hartough HD (1950) Polymerization of thiophene and
alkylthiophenes. J Am Chem Soc 72:1910–1912
34. Topchiev AV, Krentsel BA, Gol’dfarb YA (1959) Polymers of heterocycles. Izv Akad Nauk
SSSR, Ser Khim 369
35. Strelko VV, Vysotskii ZZ (1964) Polymerization of thiophene on the surface of dehydratable
silica gel. Sintez i Fiz-Khim Polimerov, Akad Nauk Ukr SSR, Inst Khim Vysokomolekul
Soedin, Sb Statei 80–82
36. Armour M, Davies AG, Upadhyay J, Wassermann A (1967) Colored, electrically conducting
polymers from furan, pyrrole, and thiophene. J Polym Sci A-1 Polym Chem 5:1527–1538
37. Ramsey JS, Kovacic P (1969) Polymerization of aromatic nuclei. XV. Polymerization of
2,5-di- and 2,3,5-trichlorothiophenes with aluminum chloride-cupric chloride. J Polym Sci
A-1 Polym Chem 7:127–138
38. Curtis RF, Jones DM, Thomas WA (1971) The ‘trimer’ and ‘pentamer’ from the polymerization of thiophene by polyphosphoric acid. J Chem Soc C 1971:234–238
39. Huber LK (1971) Thiophene polymers and method of preparation. US patent 3,557,068
40. Louvar JJ (1971) Polymerization of heterocyclic compounds. US patent 3,574,072 A
41. Tourillon G, Garnier F (1982) New electrochemically generated organic conducting polymers. J Electroanal Chem Interfacial Electrochem 135:173–178
42. Chiang CK, Fincher CR Jr, Park YW, Heeger AJ, Shirakawa H, Louis EJ, Gau SC, MacDiarmid AG (1977) Electrical conductivity in doped polyacetylene. Phys Rev Lett 39:1098–
1101
43. Yamamoto T, Sanechika K, Yamamoto A (1980) Preparation of thermostable and electricconducting poly(2,5-thienylene). J Polym Sci Polym Lett Ed 18:9–12
44. Lin JWP, Dudek LP (1980) Synthesis and properties of poly(2,5-thienylene). J Polym Sci
Polym Chem Ed 18:2869–2873
45. Tamao K, Sumitani K, Kumada M (1972) Selective carbon–carbon bond formation by crosscoupling of Grignard reagents with organic halides. Catalysis by nickel-phosphine complexes. J Amer Chem Soc 94:4374–4376
46. Tamao K, Sumitani K, Kiso Y, Zembayashi M, Fujioka A, Kodama S, Nakajima I, Minato A,
Kumada M (1976) Nickel-phosphine complex-catalyzed Grignard coupling. I. Crosscoupling of alkyl, aryl, and alkenyl Grignard reagents with aryl and alkenyl halides: general
scope and limitations. Bull Chem Soc Jpn 49:1958–1969
47. Tamao K, Kodama S, Nakajima I, Kumada M, Minato A, Suzuki K (1982) Nickel-phosphine
complex-catalyzed Grignard coupling. II. Grignard coupling of heterocyclic compounds.
Tetrahedron 38:3347–3354
48. Yamamoto T, Sanechika K, Yamamoto A (1983) Preparation and characterization of poly
(thienylenes). Bull Chem Soc Jpn 56:1497–1502
49. Yamamoto T, Morita A, Miyazaki Y, Maruyama T, Wakayama H, Zhou ZH, Nakamura Y,
Kanbara T, Sasaki S, Kubota K (1992) Preparation of π -conjugated poly(thiophene-2,5-diyl),
poly(p-phenylene), and related polymers using zerovalent nickel complexes. Linear structure
and properties of the π -conjugated polymers. Macromolecules 25:1214–1223
50. Yamamoto T, Maruyama T, Zhou ZH, Miyazaki Y, Kanbara T, Sanechika K (1991) New
method using nickel(0) complex for preparation of poly(p-phenylene), poly(2,5-thienylene)
and related π -conjugated polymers. Synthetic Met 41:345–348
Progress in the Synthesis of Poly(3-hexylthiophene)
29
Neher D (2004) Effect of molecular weight and annealing of poly(3-hexylthiophene)s on the
performance of organic field-effect transistors. Adv Funct Mater 14:757–764
30. Kline RJ, McGehee MD, Kadnikova EN, Liu J, Frechet JMJ, Toney MF (2005) Dependence
of regioregular poly(3-hexylthiophene) film morphology and field-effect mobility on molecular weight. Macromolecules 38:3312–3319
31. Meyer V (1883) Thiophene, a substance contained in coal-tar benzene. Chem Ber 16:1465–
1478
32. Meyer V (1884) The thiophene and pyrroline groups. Chem Ber 16:2968–2975
33. Meisel SL, Johnson GC, Hartough HD (1950) Polymerization of thiophene and
alkylthiophenes. J Am Chem Soc 72:1910–1912
34. Topchiev AV, Krentsel BA, Gol’dfarb YA (1959) Polymers of heterocycles. Izv Akad Nauk
SSSR, Ser Khim 369
35. Strelko VV, Vysotskii ZZ (1964) Polymerization of thiophene on the surface of dehydratable
silica gel. Sintez i Fiz-Khim Polimerov, Akad Nauk Ukr SSR, Inst Khim Vysokomolekul
Soedin, Sb Statei 80–82
36. Armour M, Davies AG, Upadhyay J, Wassermann A (1967) Colored, electrically conducting
polymers from furan, pyrrole, and thiophene. J Polym Sci A-1 Polym Chem 5:1527–1538
37. Ramsey JS, Kovacic P (1969) Polymerization of aromatic nuclei. XV. Polymerization of
2,5-di- and 2,3,5-trichlorothiophenes with aluminum chloride-cupric chloride. J Polym Sci
A-1 Polym Chem 7:127–138
38. Curtis RF, Jones DM, Thomas WA (1971) The ‘trimer’ and ‘pentamer’ from the polymerization of thiophene by polyphosphoric acid. J Chem Soc C 1971:234–238
39. Huber LK (1971) Thiophene polymers and method of preparation. US patent 3,557,068
40. Louvar JJ (1971) Polymerization of heterocyclic compounds. US patent 3,574,072 A
41. Tourillon G, Garnier F (1982) New electrochemically generated organic conducting polymers. J Electroanal Chem Interfacial Electrochem 135:173–178
42. Chiang CK, Fincher CR Jr, Park YW, Heeger AJ, Shirakawa H, Louis EJ, Gau SC, MacDiarmid AG (1977) Electrical conductivity in doped polyacetylene. Phys Rev Lett 39:1098–
1101
43. Yamamoto T, Sanechika K, Yamamoto A (1980) Preparation of thermostable and electricconducting poly(2,5-thienylene). J Polym Sci Polym Lett Ed 18:9–12
44. Lin JWP, Dudek LP (1980) Synthesis and properties of poly(2,5-thienylene). J Polym Sci
Polym Chem Ed 18:2869–2873
45. Tamao K, Sumitani K, Kumada M (1972) Selective carbon–carbon bond formation by crosscoupling of Grignard reagents with organic halides. Catalysis by nickel-phosphine complexes. J Amer Chem Soc 94:4374–4376
46. Tamao K, Sumitani K, Kiso Y, Zembayashi M, Fujioka A, Kodama S, Nakajima I, Minato A,
Kumada M (1976) Nickel-phosphine complex-catalyzed Grignard coupling. I. Crosscoupling of alkyl, aryl, and alkenyl Grignard reagents with aryl and alkenyl halides: general
scope and limitations. Bull Chem Soc Jpn 49:1958–1969
47. Tamao K, Kodama S, Nakajima I, Kumada M, Minato A, Suzuki K (1982) Nickel-phosphine
complex-catalyzed Grignard coupling. II. Grignard coupling of heterocyclic compounds.
Tetrahedron 38:3347–3354
48. Yamamoto T, Sanechika K, Yamamoto A (1983) Preparation and characterization of poly
(thienylenes). Bull Chem Soc Jpn 56:1497–1502
49. Yamamoto T, Morita A, Miyazaki Y, Maruyama T, Wakayama H, Zhou ZH, Nakamura Y,
Kanbara T, Sasaki S, Kubota K (1992) Preparation of π -conjugated poly(thiophene-2,5-diyl),
poly(p-phenylene), and related polymers using zerovalent nickel complexes. Linear structure
and properties of the π -conjugated polymers. Macromolecules 25:1214–1223
50. Yamamoto T, Maruyama T, Zhou ZH, Miyazaki Y, Kanbara T, Sanechika K (1991) New
method using nickel(0) complex for preparation of poly(p-phenylene), poly(2,5-thienylene)
and related π -conjugated polymers. Synthetic Met 41:345–348
Progress in the Synthesis of Poly(3-hexylthiophene)
29