72. Mauer R, Kastler M, Laquai F (2010) The impact of polymer regioregularity on charge
transport and efficiency of P3HT:PCBM photovoltaic devices. Adv Funct Mater 20:2085–
2092
73. Kim Y, Cook S, Tuladhar SM, Choulis SA, Nelson J, Durrant JR, Bradley DDC, Giles M,
McCulloch I, Ha C-S, Ree M (2006) A strong regioregularity effect in self-organizing
conjugated polymer films and high-efficiency polythiophene:fullerene solar cells. Nat
Mater 5:197–203
74. Maior RMS, Hinkelmann K, Eckert H, Wudl F (1990) Synthesis and characterization of two
regiochemically defined poly(dialkylbithiophenes): a comparative study. Macromolecules
23:1268–1279
75. Sato M, Morii H (1991) Nuclear magnetic resonance studies on electrochemically prepared
poly(3-dodecylthiophene). Macromolecules 24:1196–1200
76. Chen TA, Rieke RD (1992) The first regioregular head-to-tail poly(3-hexylthiophene-2,5diyl) and a regiorandom isopolymer: nickel versus palladium catalysis of 2(5)-bromo-5(2)(bromozincio)-3-hexylthiophene polymerization. J Am Chem Soc 114:10087–10088
77. McCullough RD, Lowe RD (1992) Enhanced electrical conductivity in regioselectively
synthesized poly(3-alkylthiophenes). J Chem Soc Chem Commun 1992(1):70–72
78. McCullough RD, Lowe RD, Jayaraman M, Anderson DL (1993) Design, synthesis, and
control of conducting polymer architectures: structurally homogeneous poly
(3-alkylthiophenes). J Org Chem 58:904
79. Liu J, McCullough RD (2002) End group modification of regioregular polythiophene through
postpolymerization functionalization. Macromolecules 35:9882–9889
80. Chen T-A, Wu X, Rieke RD (1995) Regiocontrolled synthesis of poly(3-alkylthiophenes)
mediated by Rieke zinc: their characterization and solid-state properties. J Am Chem Soc
117:233
81. Loewe RS, Khersonsky SM, McCullough RD (1999) A simple method to prepare head-to-tail
coupled, regioregular poly(3-alkylthiophenes) using Grignard metathesis. Adv Mater 11:250
82. Loewe RS, Ewbank PC, Liu J, Zhai L, McCullough RD (2001) Regioregular, head-to-tail
coupled poly(3-alkylthiophenes) made easy by the GRIM method: investigation of the
reaction and the origin of regioselectivity. Macromolecules 34:4324
83. Andersson MR, Mammo W, Olinga T, Svernsson M, Theander M, Inganas O (1999)
Synthesis of regio-regular phenyl substituted polythiophenes with FeCl3. Synthetic Met
101:11–12
84. Andersson MR, Selse D, Berggren M, Jaervinen H, Hjertberg T, Inganaes O,
Wennerstroem O, Oesterholm JE (1994) Regioselective polymerization of
3-(4-octylphenyl)thiophene with FeCl 3 . Macromolecules 27:6503–6506
85. Hayakawa T, Fukukawa K-I, Morishima M, Takeuchi K, Asai M, Ando S, Ueda M (2001)
Formation of regioregular head-to-tail poly[3-(4-butylphenyl)thiophene] by an oxidative
coupling polymerization with vanadium acetylacetonate. J Polym Sci A Polym Chem
39:2287–2295
86. Iraqi A, Barker GW (1998) Synthesis and characterization of telechelic regioregular head-totail poly(3-alkylthiophenes). J Mater Chem 8:25–29
87. Marsella MJ, Carroll PJ, Swager TM (1995) Design of chemoresistive sensory materials:
polythiophene-based pseudopolyrotaxanes. J Am Chem Soc 117:9832–9841
88. McCullough RD, Ewbank PC, Loewe RS (1997) Self-assembly and disassembly of
regioregular, water soluble polythiophenes: chemoselective ionchromatic sensing in water.
J Am Chem Soc 119:633–634
89. Guillerez S, Bidan G (1998) New convenient synthesis of highly regioregular poly
(3-octylthiophene) based on the Suzuki coupling reaction. Synthetic Met 93:123–126
90. Yokozawa T, Suzuki R, Nojima M, Ohta Y, Yokoyama A (2011) Precision synthesis of poly
(3-hexylthiophene) from catalyst-transfer Suzuki–Miyaura coupling polymerization.
Macromol Rapid Commun 32:801–806
Progress in the Synthesis of Poly(3-hexylthiophene)
31
transport and efficiency of P3HT:PCBM photovoltaic devices. Adv Funct Mater 20:2085–
2092
73. Kim Y, Cook S, Tuladhar SM, Choulis SA, Nelson J, Durrant JR, Bradley DDC, Giles M,
McCulloch I, Ha C-S, Ree M (2006) A strong regioregularity effect in self-organizing
conjugated polymer films and high-efficiency polythiophene:fullerene solar cells. Nat
Mater 5:197–203
74. Maior RMS, Hinkelmann K, Eckert H, Wudl F (1990) Synthesis and characterization of two
regiochemically defined poly(dialkylbithiophenes): a comparative study. Macromolecules
23:1268–1279
75. Sato M, Morii H (1991) Nuclear magnetic resonance studies on electrochemically prepared
poly(3-dodecylthiophene). Macromolecules 24:1196–1200
76. Chen TA, Rieke RD (1992) The first regioregular head-to-tail poly(3-hexylthiophene-2,5diyl) and a regiorandom isopolymer: nickel versus palladium catalysis of 2(5)-bromo-5(2)(bromozincio)-3-hexylthiophene polymerization. J Am Chem Soc 114:10087–10088
77. McCullough RD, Lowe RD (1992) Enhanced electrical conductivity in regioselectively
synthesized poly(3-alkylthiophenes). J Chem Soc Chem Commun 1992(1):70–72
78. McCullough RD, Lowe RD, Jayaraman M, Anderson DL (1993) Design, synthesis, and
control of conducting polymer architectures: structurally homogeneous poly
(3-alkylthiophenes). J Org Chem 58:904
79. Liu J, McCullough RD (2002) End group modification of regioregular polythiophene through
postpolymerization functionalization. Macromolecules 35:9882–9889
80. Chen T-A, Wu X, Rieke RD (1995) Regiocontrolled synthesis of poly(3-alkylthiophenes)
mediated by Rieke zinc: their characterization and solid-state properties. J Am Chem Soc
117:233
81. Loewe RS, Khersonsky SM, McCullough RD (1999) A simple method to prepare head-to-tail
coupled, regioregular poly(3-alkylthiophenes) using Grignard metathesis. Adv Mater 11:250
82. Loewe RS, Ewbank PC, Liu J, Zhai L, McCullough RD (2001) Regioregular, head-to-tail
coupled poly(3-alkylthiophenes) made easy by the GRIM method: investigation of the
reaction and the origin of regioselectivity. Macromolecules 34:4324
83. Andersson MR, Mammo W, Olinga T, Svernsson M, Theander M, Inganas O (1999)
Synthesis of regio-regular phenyl substituted polythiophenes with FeCl3. Synthetic Met
101:11–12
84. Andersson MR, Selse D, Berggren M, Jaervinen H, Hjertberg T, Inganaes O,
Wennerstroem O, Oesterholm JE (1994) Regioselective polymerization of
3-(4-octylphenyl)thiophene with FeCl 3 . Macromolecules 27:6503–6506
85. Hayakawa T, Fukukawa K-I, Morishima M, Takeuchi K, Asai M, Ando S, Ueda M (2001)
Formation of regioregular head-to-tail poly[3-(4-butylphenyl)thiophene] by an oxidative
coupling polymerization with vanadium acetylacetonate. J Polym Sci A Polym Chem
39:2287–2295
86. Iraqi A, Barker GW (1998) Synthesis and characterization of telechelic regioregular head-totail poly(3-alkylthiophenes). J Mater Chem 8:25–29
87. Marsella MJ, Carroll PJ, Swager TM (1995) Design of chemoresistive sensory materials:
polythiophene-based pseudopolyrotaxanes. J Am Chem Soc 117:9832–9841
88. McCullough RD, Ewbank PC, Loewe RS (1997) Self-assembly and disassembly of
regioregular, water soluble polythiophenes: chemoselective ionchromatic sensing in water.
J Am Chem Soc 119:633–634
89. Guillerez S, Bidan G (1998) New convenient synthesis of highly regioregular poly
(3-octylthiophene) based on the Suzuki coupling reaction. Synthetic Met 93:123–126
90. Yokozawa T, Suzuki R, Nojima M, Ohta Y, Yokoyama A (2011) Precision synthesis of poly
(3-hexylthiophene) from catalyst-transfer Suzuki–Miyaura coupling polymerization.
Macromol Rapid Commun 32:801–806
Progress in the Synthesis of Poly(3-hexylthiophene)
31