91. Bryan ZJ, Smith ML, McNeil AJ (2012) Chain-growth polymerization of aryl Grignards
initiated by a stabilized NHC-Pd precatalyst. Macromol Rapid Commun 33:842–847
92. Yoshikai N, Matsuda H, Nakamura E (2008) Ligand exchange as the first irreversible step in
the nickel-catalyzed cross-coupling reaction of Grignard reagents. J Am Chem Soc
130:15258–15259
93. Verswyvel M, Verstappen P, De CL, Verbiest T, Koeckelberghs G (2011) Development of a
universal chain-growth polymerization protocol of conjugated polymers: toward a variety of
all-conjugated block-copolymers. J Polym Sci A Polym Chem 49:5339–5349
94. Seyler H, Subbiah J, Jones DJ, Holmes AB, Wong WWH (2013) Controlled synthesis of poly
(3-hexylthiophene) in continuous flow. Beilstein J Org Chem 9:1492–1500
95. Sevignon M, Papillon J, Schulz E, Lemaire M (1999) New synthetic method for the
polymerization of alkylthiophenes. Tetrahedron Lett 40:5873–5876
96. Wang Q, Takita R, Kikuzaki Y, Ozawa F (2010) Palladium-catalyzed dehydrohalogenative
polycondensation of 2-Bromo-3-hexylthiophene: an efficient approach to head-to-tail poly
(3-hexylthiophene). J Am Chem Soc 132:11420–11421
97. Wang Q, Wakioka M, Ozawa F (2012) Synthesis of end-capped regioregular poly
(3-hexylthiophene)s via direct arylation. Macromol Rapid Commun 33:1203–1207
98. Rudenko AE, Wiley CA, Stone SM, Tannaci JF, Thompson BC (2012) Semi-random P3HT
analogs via direct arylation polymerization. J Polym Sci A Polym Chem 50:3691–3697
99. Mercier LG, Leclerc M (2013) Direct (hetero)arylation: a new tool for polymer chemists. Acc
Chem Res 46:1597–1605
100. Tamba S, Fuji K, Nakamura K, Mori A (2014) Nickel(II)-catalyzed cross-coupling polycondensation of thiophenes via C–S bond cleavage. Organometallics 33:12–15
101. Corriu RJP, Masse JP (1972) Activation of Grignard reagents by transition-metal complexes.
New and simple synthesis of trans-stilbenes and polyphenyls. J Chem Soc Chem Commun
1972(3):144a
102. Yamamoto T, Wakabayashi S, Osakada K (1992) Mechanism of carbon-carbon coupling
reactions of aromatic halides, promoted by Ni(COD) 2 in the presence of 2,2
0 -bipyridine and
triphenylphosphine, to give biaryls. J Organomet Chem 428:223–237
103. Miyazaki Y, Yamamoto T (1994) Characterization, properties and doping of poly
(3-alkylthiophene-2,5-diyl)s, P3RThs (R¼n-C6H13, n-C8H17, n-C12H25), prepared by
using zero-valent nickel complex. Synthetic Met 64:69–76
104. Yokoyama A, Miyakoshi R, Yokozawa T (2004) Chain-growth polymerization for poly
(3-hexylthiophene) with a defined molecular weight and a low polydispersity. Macromolecules 37:1169–1171
105. Miyakoshi R, Yokoyama A, Yokozawa T (2004) Synthesis of poly(3-hexylthiophene) with a
narrower polydispersity. Macromol Rapid Commun 25:1663–1666
106. Miyakoshi R, Yokoyama A, Yokozawa T (2005) Catalyst-transfer polycondensation. mechanism of Ni-catalyzed chain-growth polymerization leading to well-defined poly
(3-hexylthiophene). J Am Chem Soc 127:17542–17547
107. Beryozkina T, Senkovskyy V, Kaul E, Kiriy A (2008) Kumada catalyst-transfer polycondensation of thiophene-based oligomers: robustness of a chain-growth mechanism. Macromolecules 41:7817–7823
108. Kiriy A, Senkovskyy V, Sommer M (2011) Kumada catalyst-transfer polycondensation:
mechanism, opportunities, and challenges. Macromol Rapid Commun 32:1503–1517
109. Tkachov R, Senkovskyy V, Komber H, Sommer J-U, Kiriy A (2010) Random catalyst
walking along polymerized poly(3-hexylthiophene) chains in Kumada catalyst-transfer polycondensation. J Am Chem Soc 132:7803–7810
110. Sheina EE, Liu J, Iovu MC, Laird DW, McCullough RD (2004) Chain growth mechanism for
regioregular nickel-initiated cross-coupling polymerizations. Macromolecules 37:3526–3528
111. Iovu MC, Sheina EE, Gil RR, McCullough RD (2005) Experimental evidence for the quasi“living” nature of the grignard metathesis method for the synthesis of regioregular poly
(3-alkylthiophenes). Macromolecules 38:8649–8656
32
P. Sista and C.K. Luscombe
initiated by a stabilized NHC-Pd precatalyst. Macromol Rapid Commun 33:842–847
92. Yoshikai N, Matsuda H, Nakamura E (2008) Ligand exchange as the first irreversible step in
the nickel-catalyzed cross-coupling reaction of Grignard reagents. J Am Chem Soc
130:15258–15259
93. Verswyvel M, Verstappen P, De CL, Verbiest T, Koeckelberghs G (2011) Development of a
universal chain-growth polymerization protocol of conjugated polymers: toward a variety of
all-conjugated block-copolymers. J Polym Sci A Polym Chem 49:5339–5349
94. Seyler H, Subbiah J, Jones DJ, Holmes AB, Wong WWH (2013) Controlled synthesis of poly
(3-hexylthiophene) in continuous flow. Beilstein J Org Chem 9:1492–1500
95. Sevignon M, Papillon J, Schulz E, Lemaire M (1999) New synthetic method for the
polymerization of alkylthiophenes. Tetrahedron Lett 40:5873–5876
96. Wang Q, Takita R, Kikuzaki Y, Ozawa F (2010) Palladium-catalyzed dehydrohalogenative
polycondensation of 2-Bromo-3-hexylthiophene: an efficient approach to head-to-tail poly
(3-hexylthiophene). J Am Chem Soc 132:11420–11421
97. Wang Q, Wakioka M, Ozawa F (2012) Synthesis of end-capped regioregular poly
(3-hexylthiophene)s via direct arylation. Macromol Rapid Commun 33:1203–1207
98. Rudenko AE, Wiley CA, Stone SM, Tannaci JF, Thompson BC (2012) Semi-random P3HT
analogs via direct arylation polymerization. J Polym Sci A Polym Chem 50:3691–3697
99. Mercier LG, Leclerc M (2013) Direct (hetero)arylation: a new tool for polymer chemists. Acc
Chem Res 46:1597–1605
100. Tamba S, Fuji K, Nakamura K, Mori A (2014) Nickel(II)-catalyzed cross-coupling polycondensation of thiophenes via C–S bond cleavage. Organometallics 33:12–15
101. Corriu RJP, Masse JP (1972) Activation of Grignard reagents by transition-metal complexes.
New and simple synthesis of trans-stilbenes and polyphenyls. J Chem Soc Chem Commun
1972(3):144a
102. Yamamoto T, Wakabayashi S, Osakada K (1992) Mechanism of carbon-carbon coupling
reactions of aromatic halides, promoted by Ni(COD) 2 in the presence of 2,2
0 -bipyridine and
triphenylphosphine, to give biaryls. J Organomet Chem 428:223–237
103. Miyazaki Y, Yamamoto T (1994) Characterization, properties and doping of poly
(3-alkylthiophene-2,5-diyl)s, P3RThs (R¼n-C6H13, n-C8H17, n-C12H25), prepared by
using zero-valent nickel complex. Synthetic Met 64:69–76
104. Yokoyama A, Miyakoshi R, Yokozawa T (2004) Chain-growth polymerization for poly
(3-hexylthiophene) with a defined molecular weight and a low polydispersity. Macromolecules 37:1169–1171
105. Miyakoshi R, Yokoyama A, Yokozawa T (2004) Synthesis of poly(3-hexylthiophene) with a
narrower polydispersity. Macromol Rapid Commun 25:1663–1666
106. Miyakoshi R, Yokoyama A, Yokozawa T (2005) Catalyst-transfer polycondensation. mechanism of Ni-catalyzed chain-growth polymerization leading to well-defined poly
(3-hexylthiophene). J Am Chem Soc 127:17542–17547
107. Beryozkina T, Senkovskyy V, Kaul E, Kiriy A (2008) Kumada catalyst-transfer polycondensation of thiophene-based oligomers: robustness of a chain-growth mechanism. Macromolecules 41:7817–7823
108. Kiriy A, Senkovskyy V, Sommer M (2011) Kumada catalyst-transfer polycondensation:
mechanism, opportunities, and challenges. Macromol Rapid Commun 32:1503–1517
109. Tkachov R, Senkovskyy V, Komber H, Sommer J-U, Kiriy A (2010) Random catalyst
walking along polymerized poly(3-hexylthiophene) chains in Kumada catalyst-transfer polycondensation. J Am Chem Soc 132:7803–7810
110. Sheina EE, Liu J, Iovu MC, Laird DW, McCullough RD (2004) Chain growth mechanism for
regioregular nickel-initiated cross-coupling polymerizations. Macromolecules 37:3526–3528
111. Iovu MC, Sheina EE, Gil RR, McCullough RD (2005) Experimental evidence for the quasi“living” nature of the grignard metathesis method for the synthesis of regioregular poly
(3-alkylthiophenes). Macromolecules 38:8649–8656
32
P. Sista and C.K. Luscombe