169. Doubina N, Paniagua SA, Soldatova AV, Jen AKY, Marder SR, Luscombe CK (2011) Steric
effects of the initiator substituent position on the externally initiated polymerization of
2-Bromo-5-iodo-3-hexylthiophene. Macromolecules 44:512–520
170. Monnaie F, Brullot W, Verbiest T, De Winter J, Gerbaux P, Smeets A, Koeckelberghs G
(2013) Synthesis of end-group functionalized P3HT: general protocol for P3HT/nanoparticle
hybrids. Macromolecules 46:8500–8508
171. Crabtree RH (2005) The organometallic chemistry of the transition metals, 4th edn. Wiley,
Hoboken
172. Paramonov PB, Paniagua SA, Hotchkiss PJ, Jones SC, Armstrong NR, Marder SR, Bredas
J-L (2008) Theoretical characterization of the indium tin oxide surface and of its binding sites
for adsorption of phosphonic acid monolayers. Chem Mater 20:5131–5133
173. Khanduyeva N, Senkovskyy V, Beryozkina T, Bocharova V, Simon F, Nitschke M,
Stamm M, Groetzschel R, Kiriy A (2008) Grafting of poly(3-hexylthiophene) from poly
(4-bromostyrene) films by Kumada catalyst-transfer polycondensation: revealing of the
composite films structure. Macromolecules 41:7383–7389
174. Khanduyeva N, Senkovskyy V, Beryozkina T, Horecha M, Stamm M, Uhrich C, Riede M,
Leo K, Kiriy A (2009) Surface engineering using Kumada catalyst-transfer polycondensation
(KCTP): preparation and structuring of poly(3-hexylthiophene)-based graft copolymer
brushes. J Am Chem Soc 131:153–161
175. Sontag SK, Marshall N, Locklin J (2009) Formation of conjugated polymer brushes by
surface-initiated catalyst-transfer polycondensation. Chem Commun 2009(23):3354–3356
176. Huddleston NE, Sontag SK, Bilbrey JA, Sheppard GR, Locklin J (2012) Palladium-mediated
surface-initiated Kumada catalyst polycondensation: a facile route towards oriented conjugated polymers. Macromol Rapid Commun 33:2115–2120
177. Doubina N, Jenkins JL, Paniagua SA, Mazzio KA, MacDonald GA, Jen AKY, Armstrong
NR, Marder SR, Luscombe CK (2012) Surface-initiated synthesis of poly
(3-methylthiophene) from indium tin oxide and its electrochemical properties. Langmuir
28:1900–1908
178. Marshall N, Sontag SK, Locklin J (2011) Surface-initiated polymerization of conjugated
polymers. Chem Commun 47:5681–5689
179. Marshall N, Sontag SK, Locklin J (2010) Substituted poly(p-phenylene) thin films via
surface-initiated Kumada-type catalyst transfer polycondensation. Macromolecules
43:2137–2144
180. Orski SV, Fries KH, Sontag SK, Locklin J (2011) Fabrication of nanostructures using
polymer brushes. J Mater Chem 21:14135–14149
181. Kim M, Hohman JN, Cao Y, Houk KN, Ma H, Jen AKY, Weiss PS (2011) Creating favorable
geometries for directing organic photoreactions in alkanethiolate monolayers. Science
331:1312–1315
182. Chechik V, Crooks RM, Stirling CJM (2000) Reactions and reactivity in self-assembled
monolayers. Adv Mater 12:1161–1171
183. Bilbrey JA, Sontag SK, Huddleston NE, Allen WD, Locklin J (2012) On the role of
disproportionation energy in Kumada catalyst-transfer polycondensation. ACS Macro Lett
1:995–1000
184. Wong KW, Yip HL, Luo Y, Wong KY, Lau WM, Low KH, Chow HF, Gao ZQ, Yeung WL,
Chang CC (2002) Blocking reactions between indium-tin oxide and poly(3,4-ethylene
dioxythiophene):poly(styrene sulphonate) with a self-assembly monolayer. Appl Phys Lett
80:2788–2790
185. Yan H, Lee P, Armstrong NR, Graham A, Evmenenko GA, Dutta P, Marks TJ (2005) Highperformance hole-transport layers for polymer light-emitting diodes. Implementation of
organosiloxane cross-linking chemistry in polymeric electroluminescent devices. J Am
Chem Soc 127:3172–3183
186. Ma H, Yip H-L, Huang F, Jen AKY (2010) Interface engineering for organic electronics. Adv
Funct Mater 20:1371–1388
36
P. Sista and C.K. Luscombe
effects of the initiator substituent position on the externally initiated polymerization of
2-Bromo-5-iodo-3-hexylthiophene. Macromolecules 44:512–520
170. Monnaie F, Brullot W, Verbiest T, De Winter J, Gerbaux P, Smeets A, Koeckelberghs G
(2013) Synthesis of end-group functionalized P3HT: general protocol for P3HT/nanoparticle
hybrids. Macromolecules 46:8500–8508
171. Crabtree RH (2005) The organometallic chemistry of the transition metals, 4th edn. Wiley,
Hoboken
172. Paramonov PB, Paniagua SA, Hotchkiss PJ, Jones SC, Armstrong NR, Marder SR, Bredas
J-L (2008) Theoretical characterization of the indium tin oxide surface and of its binding sites
for adsorption of phosphonic acid monolayers. Chem Mater 20:5131–5133
173. Khanduyeva N, Senkovskyy V, Beryozkina T, Bocharova V, Simon F, Nitschke M,
Stamm M, Groetzschel R, Kiriy A (2008) Grafting of poly(3-hexylthiophene) from poly
(4-bromostyrene) films by Kumada catalyst-transfer polycondensation: revealing of the
composite films structure. Macromolecules 41:7383–7389
174. Khanduyeva N, Senkovskyy V, Beryozkina T, Horecha M, Stamm M, Uhrich C, Riede M,
Leo K, Kiriy A (2009) Surface engineering using Kumada catalyst-transfer polycondensation
(KCTP): preparation and structuring of poly(3-hexylthiophene)-based graft copolymer
brushes. J Am Chem Soc 131:153–161
175. Sontag SK, Marshall N, Locklin J (2009) Formation of conjugated polymer brushes by
surface-initiated catalyst-transfer polycondensation. Chem Commun 2009(23):3354–3356
176. Huddleston NE, Sontag SK, Bilbrey JA, Sheppard GR, Locklin J (2012) Palladium-mediated
surface-initiated Kumada catalyst polycondensation: a facile route towards oriented conjugated polymers. Macromol Rapid Commun 33:2115–2120
177. Doubina N, Jenkins JL, Paniagua SA, Mazzio KA, MacDonald GA, Jen AKY, Armstrong
NR, Marder SR, Luscombe CK (2012) Surface-initiated synthesis of poly
(3-methylthiophene) from indium tin oxide and its electrochemical properties. Langmuir
28:1900–1908
178. Marshall N, Sontag SK, Locklin J (2011) Surface-initiated polymerization of conjugated
polymers. Chem Commun 47:5681–5689
179. Marshall N, Sontag SK, Locklin J (2010) Substituted poly(p-phenylene) thin films via
surface-initiated Kumada-type catalyst transfer polycondensation. Macromolecules
43:2137–2144
180. Orski SV, Fries KH, Sontag SK, Locklin J (2011) Fabrication of nanostructures using
polymer brushes. J Mater Chem 21:14135–14149
181. Kim M, Hohman JN, Cao Y, Houk KN, Ma H, Jen AKY, Weiss PS (2011) Creating favorable
geometries for directing organic photoreactions in alkanethiolate monolayers. Science
331:1312–1315
182. Chechik V, Crooks RM, Stirling CJM (2000) Reactions and reactivity in self-assembled
monolayers. Adv Mater 12:1161–1171
183. Bilbrey JA, Sontag SK, Huddleston NE, Allen WD, Locklin J (2012) On the role of
disproportionation energy in Kumada catalyst-transfer polycondensation. ACS Macro Lett
1:995–1000
184. Wong KW, Yip HL, Luo Y, Wong KY, Lau WM, Low KH, Chow HF, Gao ZQ, Yeung WL,
Chang CC (2002) Blocking reactions between indium-tin oxide and poly(3,4-ethylene
dioxythiophene):poly(styrene sulphonate) with a self-assembly monolayer. Appl Phys Lett
80:2788–2790
185. Yan H, Lee P, Armstrong NR, Graham A, Evmenenko GA, Dutta P, Marks TJ (2005) Highperformance hole-transport layers for polymer light-emitting diodes. Implementation of
organosiloxane cross-linking chemistry in polymeric electroluminescent devices. J Am
Chem Soc 127:3172–3183
186. Ma H, Yip H-L, Huang F, Jen AKY (2010) Interface engineering for organic electronics. Adv
Funct Mater 20:1371–1388
36
P. Sista and C.K. Luscombe