polymerization: influence of additives and reaction conditions. J Polym Sci A Polym Chem
50:2762–2769
150. Lohwasser RH, Thelakkat M (2011) Toward perfect control of end groups and polydispersity
in poly(3-hexylthiophene) via catalyst transfer polymerization. Macromolecules 44:3388–
3397
151. Wu S, Huang L, Tian H, Geng Y, Wang F (2011) LiCl-promoted chain growth Kumada
catalyst-transfer polycondensation of the “reversed” thiophene monomer. Macromolecules
44:7558–7567
152. Kim JS, Lee Y, Lee JH, Park JH, Kim JK, Cho K (2010) High-efficiency organic solar cells
based on end-functional-group-modified poly(3-hexylthiophene). Adv Mater 22:1355–1360
153. Kim Y, Cook S, Kirkpatrick J, Nelson J, Durrant JR, Bradley DDC, Giles M, Heeney M,
Hamilton R, McCulloch I (2007) Effect of the end group of regioregular poly
(3-hexylthiophene) polymers on the performance of polymer/fullerene solar cells. J Phys
Chem C 111:8137–8141
154. Senkovskyy V, Khanduyeva N, Komber H, Oertel U, Stamm M, Kuckling D, Kiriy A (2007)
Conductive polymer brushes of regioregular head-to-tail poly(3-alkylthiophenes) via
catalyst-transfer surface-initiated polycondensation. J Am Chem Soc 129:6626–6632
155. Fahey DR (1970) Reaction of aryl and vinyl halides with nickel(O) complexes. J Am Chem
Soc 92:402–404
156. Hidai M, Kashiwagi T, Ikeuchi T, Uchida Y (1971) Oxidative additions to nickel(0).
Preparation and properties of a new series of arylnickel(II) complexes. J Organometal
Chem 30:279–282
157. Carothers WH (1929) Polymerization and ring formation. I. Introduction to the general theory
of condensation polymers. J Am Chem 51:2548–2559
158. Flory PJ (1953) Principles of polymer chemistry. Cornell University Press, New York
159. Doubina N, Ho A, Jen AKY, Luscombe CK (2009) Effect of initiators on the Kumada
catalyst-transfer polycondensation reaction. Macromolecules 42:7670–7677
160. Doubina N, Stoddard M, Bronstein HA, Jen AKY, Luscombe CK (2009) The effects of
binding ligand variation on the nickel catalyzed externally initiated polymerization of
2-bromo-3-hexyl-5-iodothiophene. Macromol Chem Phys 210:1966–1972
161. Bronstein HA, Luscombe CK (2009) Externally initiated regioregular P3HT with controlled
molecular weight and narrow polydispersity. J Am Chem Soc 131:12894–12895
162. Saito S, Oh-tani S, Miyaura N (1997) Synthesis of Biaryls via a nickel(0)-catalyzed crosscoupling reaction of chloroarenes with arylboronic acids. J Org Chem 62:8024–8030
163. Wolfe JP, Buchwald SL (1997) Nickel-catalyzed amination of aryl chlorides. J Am Chem Soc
119:6054–6058
164. Senkovskyy V, Tkachov R, Beryozkina T, Komber H, Oertel U, Horecha M, Bocharova V,
Stamm M, Gevorgyan SA, Krebs FC, Kiriy A (2009) “Hairy” poly(3-hexylthiophene)
particles prepared via surface-initiated Kumada catalyst-transfer polycondensation. J Am
Chem Soc 131:16445–16453
165. Chavez CA, Choi J, Nesterov EE (2014) One-step simple preparation of catalytic initiators
for catalyst-transfer Kumada polymerization: synthesis of defect-free polythiophenes. Macromolecules 47:506–516
166. Senkovskyy V, Sommer M, Tkachov R, Komber H, Huck WTS, Kiriy A (2010) Convenient
route to initiate Kumada catalyst-transfer polycondensation using Ni(dppe)Cl2 or Ni(dppp)
Cl2 and sterically hindered Grignard compounds. Macromolecules 43:10157–10161
167. Chatt J, Shaw BL (1960) Alkyls and aryls of transition metals. III. Nickel(II) derivatives.
J Chem Soc 1718–1729
168. Smeets A, Van den Bergh K, De Winter J, Gerbaux P, Verbiest T, Koeckelberghs G (2009)
Incorporation of different end groups in conjugated polymers using functional nickel initiators. Macromolecules 42:7638–7641
Progress in the Synthesis of Poly(3-hexylthiophene)
35
50:2762–2769
150. Lohwasser RH, Thelakkat M (2011) Toward perfect control of end groups and polydispersity
in poly(3-hexylthiophene) via catalyst transfer polymerization. Macromolecules 44:3388–
3397
151. Wu S, Huang L, Tian H, Geng Y, Wang F (2011) LiCl-promoted chain growth Kumada
catalyst-transfer polycondensation of the “reversed” thiophene monomer. Macromolecules
44:7558–7567
152. Kim JS, Lee Y, Lee JH, Park JH, Kim JK, Cho K (2010) High-efficiency organic solar cells
based on end-functional-group-modified poly(3-hexylthiophene). Adv Mater 22:1355–1360
153. Kim Y, Cook S, Kirkpatrick J, Nelson J, Durrant JR, Bradley DDC, Giles M, Heeney M,
Hamilton R, McCulloch I (2007) Effect of the end group of regioregular poly
(3-hexylthiophene) polymers on the performance of polymer/fullerene solar cells. J Phys
Chem C 111:8137–8141
154. Senkovskyy V, Khanduyeva N, Komber H, Oertel U, Stamm M, Kuckling D, Kiriy A (2007)
Conductive polymer brushes of regioregular head-to-tail poly(3-alkylthiophenes) via
catalyst-transfer surface-initiated polycondensation. J Am Chem Soc 129:6626–6632
155. Fahey DR (1970) Reaction of aryl and vinyl halides with nickel(O) complexes. J Am Chem
Soc 92:402–404
156. Hidai M, Kashiwagi T, Ikeuchi T, Uchida Y (1971) Oxidative additions to nickel(0).
Preparation and properties of a new series of arylnickel(II) complexes. J Organometal
Chem 30:279–282
157. Carothers WH (1929) Polymerization and ring formation. I. Introduction to the general theory
of condensation polymers. J Am Chem 51:2548–2559
158. Flory PJ (1953) Principles of polymer chemistry. Cornell University Press, New York
159. Doubina N, Ho A, Jen AKY, Luscombe CK (2009) Effect of initiators on the Kumada
catalyst-transfer polycondensation reaction. Macromolecules 42:7670–7677
160. Doubina N, Stoddard M, Bronstein HA, Jen AKY, Luscombe CK (2009) The effects of
binding ligand variation on the nickel catalyzed externally initiated polymerization of
2-bromo-3-hexyl-5-iodothiophene. Macromol Chem Phys 210:1966–1972
161. Bronstein HA, Luscombe CK (2009) Externally initiated regioregular P3HT with controlled
molecular weight and narrow polydispersity. J Am Chem Soc 131:12894–12895
162. Saito S, Oh-tani S, Miyaura N (1997) Synthesis of Biaryls via a nickel(0)-catalyzed crosscoupling reaction of chloroarenes with arylboronic acids. J Org Chem 62:8024–8030
163. Wolfe JP, Buchwald SL (1997) Nickel-catalyzed amination of aryl chlorides. J Am Chem Soc
119:6054–6058
164. Senkovskyy V, Tkachov R, Beryozkina T, Komber H, Oertel U, Horecha M, Bocharova V,
Stamm M, Gevorgyan SA, Krebs FC, Kiriy A (2009) “Hairy” poly(3-hexylthiophene)
particles prepared via surface-initiated Kumada catalyst-transfer polycondensation. J Am
Chem Soc 131:16445–16453
165. Chavez CA, Choi J, Nesterov EE (2014) One-step simple preparation of catalytic initiators
for catalyst-transfer Kumada polymerization: synthesis of defect-free polythiophenes. Macromolecules 47:506–516
166. Senkovskyy V, Sommer M, Tkachov R, Komber H, Huck WTS, Kiriy A (2010) Convenient
route to initiate Kumada catalyst-transfer polycondensation using Ni(dppe)Cl2 or Ni(dppp)
Cl2 and sterically hindered Grignard compounds. Macromolecules 43:10157–10161
167. Chatt J, Shaw BL (1960) Alkyls and aryls of transition metals. III. Nickel(II) derivatives.
J Chem Soc 1718–1729
168. Smeets A, Van den Bergh K, De Winter J, Gerbaux P, Verbiest T, Koeckelberghs G (2009)
Incorporation of different end groups in conjugated polymers using functional nickel initiators. Macromolecules 42:7638–7641
Progress in the Synthesis of Poly(3-hexylthiophene)
35