Direct arylation polymerization: A green, streamlining synthetic approach to π-conjugated polymers

Current Organic Chemistry

Volumn 17, Issue 9, 2013, Pages 999-1012

  Wang, Kai ^a   Wang, Mingfeng ^a  

^a Nanyang Technological University   (Singapore)

Author keywords

C H activation; Direct arylation; Palladium catalyst; Polymerization; conjugated polymers

Indexed keywords

ACTIVATION ANALYSIS; AROMATIC COMPOUNDS; CATALYSTS; CONJUGATED POLYMERS; FIELD EFFECT TRANSISTORS; OPTOELECTRONIC DEVICES; PALLADIUM; POLYMERIZATION; SYNTHESIS (CHEMICAL);

ARYL-ARYL COUPLING; ARYLATIONS; BOND ACTIVATION; C-H ACTIVATION; C-H BOND; DIRECT ARYLATION; METAL-CATALYZED; PALLADIUM CATALYST; SYNTHETIC APPROACH; Π-CONJUGATED POLYMER;

CHEMICAL ACTIVATION;

EID: 84878602946     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/1385272811317090011     Document Type: Article

References (111)

1. Halls, J. J. M.; Walsh, C. A.; Greenham, N. C.; Marseglia, E. A.; Friend, R. H.; Moratti, S. C.; Holmes, A. B., Efficient photodiodes from interpenetrating polymer networks. Nature, 1995, 376 (6540), 498-500.
2. Yu, G.; Gao, J.; Hummelen, J. C.; Wudl, F.; Heeger, A. J., Polymer Photovoltaic Cells: Enhanced Efficiencies via a Network of Internal Donor-Acceptor Heterojunctions. Science, 1995, 270 (5243), 1789-1791.
3. Shaheen, S. E.; Brabec, C. J.; Sariciftci, N. S.; Padinger, F.; Fromherz, T.; Hummelen, J. C., 2.5% efficient organic plastic solar cells. Appl. Phys. Lett., 2001, 78 (6), 841-843.
4. Brabec, C. J.; Sariciftci, N. S.; Hummelen, J. C., Plastic Solar Cells. Adv. Funct. Mater., 2001, 11, 15-26.
5. Scharber, M. C.; Mühlbacher, D.; Koppe, M.; Denk, P.; Waldauf, C.; Heeger, A. J.; Brabec, C. J., Design Rules for Donors in Bulk-Heterojunction Solar Cells-Towards 10% Energy-Conversion Efficiency. Adv. Mater., 2006, 18 (6), 789-794.
6. Gunes, S.; Neugebauer, H.; Sariciftci, N. S., Conjugated polymer-based organic solar cells. Chem. Rev., 2007, 107 (4), 1324-1338.
7. Peet, J.; Kim, J. Y.; Coates, N. E.; Ma, W. L.; Moses, D.; Heeger, A. J.; Bazan, G. C., Efficiency enhancement in low-bandgap polymer solar cells by processing with alkane dithiols. Nat. Mater., 2007, 6 (7), 497-500.
8. Thompson, B. C.; Frechet, J. M. J., Organic photovoltaics-Polymerfullerene composite solar cells. Angew. Chem. Int. Ed., 2008, 47 (1), 58-77.
9. Chen, J. W.; Cao, Y., Development of Novel Conjugated Donor Polymers for High-Efficiency Bulk-Heterojunction Photovoltaic Devices. Acc. Chem. Res., 2009, 42 (11), 1709-1718.
10. Cheng, Y. J.; Yang, S. H.; Hsu, C. S., Synthesis of Conjugated Polymers for Organic Solar Cell Applications. Chem. Rev., 2009, 109 (11), 5868-5923.
11. Brunetti, F. G.; Kumar, R.; Wudl, F., Organic electronics from perylene to organic photovoltaics: painting a brief history with a broad brush. J. Mater. Chem., 2010, 20 (15), 2934-2948.
12. Liang, Y. Y.; Yu, L. P., A New Class of Semiconducting Polymers for Bulk Heterojunction Solar Cells with Exceptionally High Performance. Acc. Chem. Res., 2010, 43 (9), 1227-1236.
13. Chochos, C. L.; Choulis, S. A., How the structural deviations on the backbone of conjugated polymers influence their optoelectronic properties and photovoltaic performance. Prog. Polym. Sci., 2011, 36 (10), 1326-1414.
14. Li, Y. F., Molecular Design of Photovoltaic Materials for Polymer Solar Cells: Toward Suitable Electronic Energy Levels and Broad Absorption. Acc. Chem. Res., 2012, 45 (5), 723-733.
15. Li, G.; Zhu, R.; Yang, Y., Polymer solar cells. Nature Photon., 2012, 6 (3), 153-161.
16. Wang, M. F.; Wudl, F., Top-down meets bottom-up: organized donor- acceptor heterojunctions for organic solar cells. J. Mater. Chem., 2012, 22 (46), 24297-24314.
17. Burroughes, J. H.; Bradley, D. D. C.; Brown, A. R.; Marks, R. N.; Mackay, K.; Friend, R. H.; Burns, P. L.; Holmes, A. B., Light-emitting diodes based on conjugated polymers. Nature, 1990, 347 (6293), 539-541.
18. Luo, J.; Li, X.; Hou, Q.; Peng, J. B.; Yang, W.; Cao, Y., High-Efficiency White-Light Emission from a Single Copolymer: Fluorescent Blue, Green, and Red Chromophores on a Conjugated Polymer Backbone. Adv. Mater., 2007, 19 (8), 1113-1117.
19. Cui, Y. T.; Zhang, X. J.; Jenekhe, S. A., Thiophene-Linked Polyphenylquinoxaline A New Electron Transport Conjugated Polymer for LED. Macromolecules, 1999, 32, 3824-3826.
20. Bao, Z. N.; Peng, Z. H.; Galvin, M. E.; Chandross, E. A., Novel Oxadiazole Side Chain Conjugated Polymers as Single-Layer LED with Improved QY. Chem. Mater., 1998, 10 (5), 1201-1204.
21. Hoven, C. V.; Garcia, A.; Bazan, G. C.; Nguyen, T. Q., Recent Applications of Conjugated Polyelectrolytes in Optoelectronic Devices. Adv. Mater., 2008, 20 (20), 3793-3810.
22. Zhong, C. M.; Duan, C. H.; Huang, F.; Wu, H. B.; Cao, Y., Materials and Devices toward Fully Solution Processable Organic Light-Emitting Diodes. Chem. Mater., 2011, 23 (3), 326-340.
23. Wu, J.-S.; Lin, C.-T.; Wang, C.-L.; Cheng, Y.-J.; Hsu, C.-S., New Angular-Shaped and Isomerically Pure Anthradithiophene with Lateral Aliphatic Side Chains for Conjugated Polymers: Synthesis, Characterization, and Implications for Solution-Prossessed Organic Field-Effect Transistors and Photovoltaics. Chem. Mater., 2012, 24 (12), 2391-2399.
24. Sirringhaus, H.; Tessler, N.; Thomas, D. S.; Brown, P. J.; Friend, R. H., High-Mobility Conjugated Polymer Field-Effect Transistors. Adv. Solid State Phys., 1999, 39, 101-110.
25. Sirringhaus, H.; Tessler, N.; Friend, R. H., Integrated Optoelectronic Devices Based on Conjugated Polymers. Science, 1998, 280 (5370), 1741-1744.
26. Usta, H.; Facchetti, A.; Marks, T. J., n-Channel Semiconductor Materials Design for Organic Complementary Circuits. Acc. Chem. Res., 2011, 44 (7), 501-510.
27. Wang, C. L.; Dong, H. L.; Hu, W. P.; Liu, Y. Q.; Zhu, D. B., Semiconducting pi-Conjugated Systems in Field-Effect Transistors: A Material Odyssey of Organic Electronics. Chem. Rev., 2012, 112 (4), 2208-2267.
28. Guo, Y. L.; Yu, G.; Liu, Y. Q., Functional Organic Field-Effect Transistors. Adv. Mater., 2010, 22 (40), 4427-4447.
29. Katz, H. E.; Bao, Z. N.; Gilat, S. L., Synthetic chemistry for ultrapure, processable, and high-mobility organic transistor semiconductors. Acc. Chem. Res., 2001, 34 (5), 359-369.
30. Sokolov, A. N.; Tee, B. C. K.; Bettinger, C. J.; Tok, J. B. H.; Bao, Z. N., Chemical and Engineering Approaches To Enable Organic Field-Effect Transistors for Electronic Skin Applications. Acc. Chem. Res., 2012, 45 (3), 361-371.
31. Ho, H. A.; Boissinot, M.; Bergeron, M. G.; Corbeil, G.; Dore, K.; Boudreau, D.; Leclerc, M., Colorimetric and fluorometric detection of nucleic acids using cationic polythiophene derivatives. Angew. Chem. Int. Ed., 2002, 41 (9), 1548-1551.
32. Duarte, A.; Pu, K. Y.; Liu, B.; Bazan, G. C., Recent Advances in Conjugated Polyelectrolytes for Emerging Optoelectronic Applications. Chem. Mater., 2011, 23 (3), 501-515.
33. Thomas III, S. W.; Joly, G. D.; Swager, T. M., Chemical Sensors Based on Amplifying Fluorescent Conjugated Polymers. Chem. Rev., 2007, 107, 1339-1386.
34. McQuade, D. T.; Pullen, A. E.; Swager, T. M., Conjugated polymer-based chemical sensors. Chem. Rev., 2000, 100, 2537-2574.
35. Zhu, C. L.; Liu, L. B.; Yang, Q.; Lv, F. T.; Wang, S., Water-Soluble Conjugated Polymers for Imaging, Diagnosis, and Therapy. Chem. Rev., 2012, 112 (8), 4687-4735.
36. The Nobel Prize in Chemistry 2000 http://www.nobelprize.org/nobel_prizes/chemistry/laureates/2000/.
37. Shirakawa, H.; Louis, E. J.; Macdiarmid, A. G.; Chiang, C. K.; Heeger, A. J., Synthesis of electrically conducting organic polymers: halogen derivatives of polyacetylene, (CH)x. J. Chem. Soc. Chem. Commun., 1977, (16), 578-580.
38. Chiang, C. K.; Fincher, C. R.; Park, Y. W.; Heeger, A. J.; Shirakawa, H.; Louis, E. J.; Gau, S. C.; Macdiarmid, A. G., Electrical Conductivity in Doped Polyacetylene. Phy. Rev. Lett., 1977, 39 (17), 1098-1101.
39. Guo, X.; Puniredd, S. R.; Baumgarten, M.; Pisula, W.; Mullen, K., Benzotrithiophene-Based Donor-Acceptor Copolymers with Distinct Supramolecular Organizations. J. Am. Chem. Soc., 2012, 134 (20), 8404-8407.
40. Beaujuge, P. M.; Frechet, J. M. J., Molecular Design and Ordering Effects in pi-Functional Materials for Transistor and Solar Cell Applications. J. Am. Chem. Soc., 2011, 133 (50), 20009-20029.
41. Osaka, I.; McCullough, R. D., Advances in molecular design and synthesis of regioregular polythiophenes. Acc. Chem. Res., 2008, 41 (9), 1202-1214.
42. Yokozawa, T.; Yokoyama, A., Chain-Growth Condensation Polymerization for the Synthesis of Well-Defined Condensation Polymers and pi-Conjugated Polymers. Chem. Rev., 2009, 109 (11), 5595-5619.
43. Shaheen, S. E.; Vangeneugden, D.; Kiebooms, R.; Vanderzande, D.; Fromherz, T.; Padinger, F.; Brabec, C. J.; Sariciftci, N. S., Low band-gap polymeric photovoltaic devices. Syn. Met., 2001, 121 (1-3), 1583-1584.
44. Ogawa, K.; Rasmussen, S. C., N-Functionalized Poly(dithieno pyrrole)s. Macromolecules, 2006, 39, 1771-1778.
45. Vangeneugden, D. L.; Vanderzande, D. J. M.; Salbeck, J.; van Hal, P. A.; Janssen, R. A. J.; Hummelen, J. C.; Brabec, C. J.; Shaheen, S. E.; Sariciftci, N. S., Synthesis and Characterization of a Poly(1,3-dithienylisothianaphthene) Derivative for Bulk Heterojunction Photovoltaic Cells. J. Phys. Chem. B, 2001, 105, 11106-11113.
46. Francesco, B.; Gianluca, M. F.; Francesco, N., Synthesis of conjugated oligomers and polymers the organometallic way. J. Mater. Chem., 2004, 14, 11-34.
47. Demadrille, R.; Delbosc, N.; Kervella, Y.; Firon, M.; de Bettignies R.; Billon, M.; Rannou, P.; Pron, A., Conjugated alternating copolymer of dialkylquaterthiophene and fluorenone: synthesis, characterisation and photovoltaic properties. J. Mater. Chem., 2007, 17 (44), 4661-4669.
48. Demadrille, R.; Firon, M.; Leroy, J.; Rannou, P.; Pron, A., Plastic Solar Cells Based on Fluorenone-Containing Oligomers and Copolymers. Adv. Funct. Mater., 2005, 15, 1547-1552.
49. Tamao, K.; Sumitani, K.; Kumada, M., Selective carbon-carbon bond formation by cross-coupling of Grignard reagents with organic halides. Catalysis by nickel-phosphine complexes. J. Am. Chem. Soc., 1972, 94 (12), 4374-4376.
50. Stille, J. K., The Palladium-Catalyzed Cross-Coupling Reactions of Organotin Reagents with Organic Electrophiles. Angew. Chem. Int. Ed., 1986, 25 (6), 508-523.
51. Carsten, B.; He, F.; Son, H. J.; Xu, T.; Yu, L. P., Stille Polycondensation for Synthesis of Functional Materials. Chem. Rev., 2011, 111 (3), 1493-1528.
52. Miyaura, N.; Suzuki, A., Palladium-catalyzed cross-coupling reaction of organoboron compounds with organic triflates. Chem. Rev., 1995, 95 (7), 2457-2483.
53. Sonogashira, K., Development of Pd-Cu catalyzed cross-coupling of terminal acetylenes with sp(2)-carbon halides. J. Organomet. Chem., 2002, 653 (1-2), 46-49.
54. Hassan, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M., Aryl-Aryl Bond Formation One Century after the Discovery of the Ullmann Reaction. Chem. Rev., 2002, 102, 1359-1469.
55. Alberico, D.; Scott, M. E.; Lautens, M., Aryl-Aryl Bond Formation by Transition-Metal-Catalyzed Direct Arylation. Chem. Rev., 2007, 107, 174-238.
56. Ackermann, L.; Vicente, R.; Kapdi, A. R., Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage. Angew. Chem. Int. Ed., 2009, 48 (52), 9792-9826.
57. Ackermann, L.; Althammer, A.; Fenner, S., Palladium-catalyzed direct arylations of heteroarenes with tosylates and mesylates. Angew. Chem. Int. Ed., 2009, 48 (1), 201-204.
58. Satoh, T.; Miura, M., Catalytic Direct Arylation of Heteroaromatic Compounds. Chem. Lett., 2007, 36 (2), 200-205.
59. Bellina, F.; Rossi, R., Transition Metal-Catalyzed Direct Arylation of Substrates with Activated sp(3)-Hybridized C-H Bonds and Some of Their Synthetic Equivalents with Aryl Halides or Pseudohalides. Chem. Rev., 2010, 110 (6), 3850-3850.
60. Gorelsky, S. I.; Lapointe, D.; Fagnou, K., Analysis of the Concerted Metalation-Deprotonation Mechanism in Palladium-Catalyzed Direct Arylation Across a Broad Range of Aromatic Substrates. J. Am. Chem. Soc., 2008, 130, 10848-10849.
61. Liegault, B.; Lapointe, D.; Caron, L.; Vlassova, A.; Fagnou, K., Establishment of Broadly Applicable Reaction Conditions for the Palladium-Catalyzed Direct Arylation of Heteroatom-Containing Aromatic Compounds. J. Org. Chem., 2009, 74, 1826-1834.
62. Facchetti, A.; Vaccaro, L.; Marrocchi, A., Semiconducting Polymers Prepared by Direct Arylation Polycondensation. Angew. Chem. Int. Ed., 2012, 51 (15), 3520-3523.
63. McCullough, R. D., The Chemistry of Conducting Polythiophenes. Adv. Mater., 1998, 10 (93), 93-116.
64. Andersson, M. R.; Thomas, O.; Mammo, W.; Svensson, M.; Theander, M.; Inganäs, O., Substituted polythiophenes designed for optoelectronic devices and conductors. J. Mater. Chem., 1999, 9, 1933-1940.
65. Li, G.; Shrotriya, V.; Huang, J.; Yao, Y.; Moriarty, T.; Emery, K.; Yang, Y., High-efficiency solution processable polymer photovoltaic cells by selforganization of polymer blends. Nat. Mater., 2005, 4 (11), 864-868.
66. Sirringhaus, H.; Brown, P. J.; Friend, R. H.M.N.; Bechgaard, K.; Langeveld-Voss, B. M. W.; Spiering, A. J. H.; Janssen, R. A. J.; Meijer, E. W.; Herwig, P.; de Leeuw, D. M., Two-dimensional charge transport in selforganized, high-mobility conjugated polymers. Nature, 1999, 401, 685-688.
67. McCullough, R. D.; Lowe, R. D., Enhanced electrical conductivity in regioselectively synthesized poly(3-alkylthiophenes). J. Chem. Soc. Chem. Commun., 1992, (1), 70-72.
68. McCullough, R. D.; Lowe, R. D.; Jayaraman, M.; Anderson, D. L., Design, synthesis, and control of conducting polymer architectures structurally homogeneous poly(3-alkylthiophenes). J. Org. Chem., 1993, 58, 904-912.
69. Chen, T.-A.; Rieke, R. D., The first regioregular head-to-tail poly(3-hexylthiophene-2,5-diyl. J. Am. Chem. Soc., 1992, 114, 10087-10088.
70. Loewe, R. S.; Khersonsky, S. M.; McCullough, R. D., A Simple Method to Prepare Head-to-Tail Coupled, Regioregular Poly(3-alkylthiophenes) Using Grignard Metathesis. Adv. Mater., 1999, 11 (3), 250-253.
71. Guillerez, S.; Bidan, G., New convenient synthesis of highly regioregular poly(3-octylthiophene) based on the Suzuki coupling reaction. Synth. Met., 1998, 93, 123-126.
72. Iraqi, A.; Barker, W., Synthesis and characterisation of telechelic regioregular head-to-tail poly(3-alkylthiophenes). J. Mater. Chem., 1998, 8, 25-29.
73. Sevignon, M.; Papillon, J.; Schulz, E.; Lemaire, M., New synthetic method for the polymerization of alkylthiophenes. Tetrahedron Lett., 1999, 40 (32), 5873-5876.
74. Hassan, J.; Schulz, E.; Gozzi, C.; Lemaire, M., Palladium-catalyzed synthesis of oligo(alkylthiophenes). J. Mol. Catal. A: Chem., 2003, 195 (1-2), 125-131.
75. Wang, Q.; Takita, R.; Kikuzaki, Y.; Ozawa, F., Palladium-Catalyzed Dehydrohalogenative Polycondensation of 2-Bromo-3-hexylthiophene: An Efficient Approach to Head-to-Tail Poly(3-hexylthiophene). J. Am. Chem. Soc., 2010, 132 (33), 11420-11421.
76. Herrmann, W. A.; Brossmer, C.; Ofele, K.; Reisinger, C.-P.; Riermeier, T. H.; Beller, M.; Fischer, H., Palladacycles as Structurally Defined Catalysts for the Heck Olefination of Chloro-and Bromoarenes. Angew. Chem. Int. Ed., 1995, 34 (17), 1844-1848.
77. Herrmann, W. A.; Brossmer, C.; Reisinger, C.-P.; Riermeier, T. H.; Ofele, K.; Beller, M., Palladacycles Efficient New Catalysts for the Heck Vinylation of Aryl Halides. Chem. Eur. J., 1997, 3 (8), 1357-1364.
78. Wang, Q.; Wakioka, M.; Ozawa, F., Synthesis of End-capped Regioregular Poly(3-hexylthiophene)s via Direct Arylation. Macromol. Rapid Commun., 2012, 33 (14), 1203-1207.
79. Rudenko, A. E.; Wiley, C. A.; Stone, S. M.; Tannaci, J. F.; Thompson, B. C., Semi-random P3HT analogs via direct arylation polymerization. J. Polym. Sci. Polym. Chem., 2012, 50 (18), 3691-3697.
80. Schwendeman, I.; Gaupp, C. L.; Hancock, J. M.; Groenendaal, L.; Reynolds, J. R., Perfluoroalkanoate-Substituted PEDOT for Electrochromic Device Applications. Adv. Funct. Mater., 2003, 13 (7), 541-547.
81. Groenendaal, L.; Jonas, F.; Freitag, D.; Pielartzik, H.; Reynolds, J. R., PEDOT and Its Derivatives Past, Present, and Future. Adv. Mater., 2000, 12 (7), 481-494.
82. Nielsen, C. B.; Angerhofer, A.; Abboud, K. A.; Reynolds, J. R., Discrete Photopatternable π-Conjugated Oligomers for Electrochromic Devices. J. Am. Chem. Soc., 2008, 130, 9734-9746.
83. Roncali, J.; Blanchard, P.; Frere, P., 3,4-Ethylenedioxythiophene (EDOT) as a versatile building block for advanced functional π -conjugated systems. J. Mater. Chem., 2005, 15 (16), 1589-1610.
84. Winther-Jensen, B.; Winther-Jensen, O.; Forsyth, M.; Macfarlane, D. R., High rates of oxygen reduction over a vapor phase-polymerized PEDOT electrode. Science, 2008, 321 (5889), 671-674.
85. Bazaco, R. B.; Gómez, R.; Seoane, C.; Bäuerle, P.; Segura, J. L., Specific recognition of a nucleobase-functionalized poly(3,4-ethylenedioxithiophene) (PEDOT) in aqueous media. Tetrahedron Lett., 2009, 50 (28), 4154-4157.
86. Hong, X.; Tyson, J. C.; Middlecoff, J. S.; Collard, D. M., Synthesis and Oxidative Polymerization of Semifluoroalkyl-Substituted Thiophenes. Macromolecules, 1999, 32, 4232-4239.
87. Jeffries-Ei, M.; Sauve, G.; McCullough, R. D., Facile Synthesis of End-Functionalized Regioregular Poly(3-alkylthiophene)s via Modified Grignard Metathesis. Macromolecules, 2005, 38, 10346-10352.
88. Iovu, M. C.; Sheina, E. E.; Gil, R. R.; McCullough, R. D., Experimental Evidence for the Quasi-"Living" Nature of the Grignard Metathesis Method for the Synthesis of Regioregular Poly(3-alkylthiophenes). Macromolecules, 2005, 38, 8649-8656.
89. Loewe, R. S.; Ewbank, P. C.; Liu, J. S.; Zhai, L.; McCullough, R. D., Regioregular, Head-to-Tail Coupled Poly(3-alkylthiophenes) Made Easy by the GRIM Method Investigation of the Reaction and the Origin of Regioselectivity. Macromolecules, 2001, 34, 4324-4233.
90. Zhao, H.; Liu, C.-Y.; Luo, S.-C.; Zhu, B.; Wang, T.-H.; Hsu, H.-F.; Yu, H.-h., Facile Syntheses of Dioxythiophene-Based Conjugated Polymers by Direct C-H Arylation. Macromolecules, 2012, 45 (19), 7783-7790.
91. Kumar, A.; Kumar, A., Single step reductive polymerization of functional 3,4-propylenedioxythiophenes via direct C-H arylation catalyzed by palladium acetate. Polym. Chem., 2010, 1 (3), 286-288.
92. Lu, W.; Kuwabara, J.; Kanbara, T., Polycondensation of Dibromofluorene Analogues with Tetrafluorobenzene via Direct Arylation. Macromolecules, 2011, 44 (6), 1252-1255.
93. Lu, W.; Kuwabara, J.; Iijima, T.; Higashimura, H.; Hayashi, H.; Kanbara, T., Synthesis of π-Conjugated Polymers Containing Fluorinated Arylene Units via Direct Arylation: Efficient Synthetic Method of Materials for OLEDs. Macromolecules, 2012, 45 (10), 4128-4133.
94. Lapointe, D.; Fagnou, K., Overview of the Mechanistic Work on the Concerted Metallation-Deprotonation Pathway. Chem. Lett., 2010, 39 (11), 1118-1126.
95. Ackermann, L., Carboxylate-assisted transition-metal-catalyzed C-H bond functionalizations: mechanism and scope. Chem. Rev., 2011, 111 (3), 1315-1345.
96. Fujinami, Y.; Kuwabara, J.; Lu, W.; Hayashi, H.; Kanbara, T., Synthesis of Thiophene-and Bithiophene-Based Alternating Copolymers via Pd-Catalyzed Direct C-H Arylation. ACS Macro Lett., 2012, 1 (1), 67-70.
97. Kroon, R.; Lenes, M.; Hummelen, J. C.; Blom, P. W. M.; De Boer, B., Small bandgap polymers for organic solar cells (polymer material development in the last 5 years). Polym. Rev., 2008, 48 (3), 531-582.
98. Boudreault, P.-L. T.; Najari, A.; Leclerc, M., Processable Low-Bandgap Polymers for Photovoltaic Applications. Chem. Mater., 2011, 23 (3), 456-469.
99. Wudl, F.; Kobayashi, M.; Heeger, A. J., Poly(isothianaphthene). J. Org. Chem., 1984, 49 (18), 3382-3384.
100. Scharber, M. C.; Koppe, M.; Gao, J.; Cordella, F.; Loi, M. A.; Denk, P.; Morana, M.; Egelhaaf, H. J.; Forberich, K.; Dennler, G.; Gaudiana, R.; Waller, D.; Zhu, Z.; Shi, X.; Brabec, C. J., Influence of the bridging atom on the performance of a low-bandgap bulk heterojunction solar cell. Adv. Mater., 2010, 22 (3), 367-370.
101. Tsao, H. N.; Cho, D. M.; Park, I.; Hansen, M. R.; Mavrinskiy, A.; Yoon, D. Y.; Graf, R.; Pisula, W.; Spiess, H. W.; Mullen, K., Ultrahigh Mobility in Polymer Field-Effect Transistors by Design. J. Am. Chem. Soc., 2011, 133 (8), 2605-2612.
102. Kowalski, S.; Allard, S.; Scherf, U., Synthesis of Poly(4,4-dialkylcyclopenta[ 2,1-b:3,4-b′]dithiophene-alt-2,1,3-benzothiadiazole) (PCPDTBT) in a Direct Arylation Scheme. ACS Macro Lett., 2012, 1 (4), 465-468.
103. Tan, Y.; Hartwig, J. F., Assessment of the intermediacy of arylpalladium carboxylate complexes in the direct arylation of benzene: evidence for C-H bond cleavage by ligandless species. J. Am. Chem. Soc., 2011, 133 (10), 3308-3011.
104. Chang, S.-W.; Waters, H.; Kettle, J.; Kuo, Z.-R.; Li, C.-H.; Yu, C.-Y.; Horie, M., Pd-Catalysed Direct Arylation Polymerisation for Synthesis of Low-Bandgap Conjugated Polymers and Photovoltaic Performance. Macromol. Rapid Commun., 2012, 33 (22), 1927-1932.
105. Horie, M.; Majewski, L. A.; Fearn, M. J.; Yu, C.-Y.; Luo, Y.; Song, A.; Saunders, B. R.; Turner, M. L., Cyclopentadithiophene based polymers-a comparison of optical, electrochemical and organic field-effect transistor characteristics. J. Mater. Chem., 2010, 20 (21), 4347-4355.
106. Berrouard, P.; Najari, A.; Pron, A.; Gendron, D.; Morin, P.-O.; Pouliot, J.-R.; Veilleux, J.; Leclerc, M., Synthesis of 5-Alkyl[3,4-c]thienopyrrole-4,6-dione-Based Polymers by Direct Heteroarylation. Angew. Chem. Int. Ed., 2012, 51 (9), 2068-2071.
107. Najari, A.; Berrouard, P.; Ottone, C.; Boivin, M.; Zou, Y. P.; Gendron, D.; Caron, W. O.; Legros, P.; Allen, C. N.; Sadki, S.; Leclerc, M., High Open-Circuit Voltage Solar Cells Based on New Thieno[3,4-c]pyrrole-4,6-dione and 2,7-Carbazole Copolymers. Macromolecules, 2012, 45 (4), 1833-1838.
108. Allard, N.; Najari, A.; Pouliot, J.-R.; Pron, A.; Grenier, F.; Leclerc, M., Easy and versatile synthesis of new poly(thieno[3,4-d]thiazole)s. Polym. Chem., 2012, 3 (10), 2875-2879.
109. Abdo, N. I.; El-Shehawy, A. A.; El-Barbary, A. A.; Lee, J.-S., Palladium-Catalyzed Direct C-H Arylation of Thieno[3,4-b]pyrazines: Synthesis of Advanced Oligomeric and Polymeric Materials. Eur. J. Org. Chem., 2012, 2012 (28), 5540-5551.
110. Lafrance, M.; Fagnou, K., Palladium-Catalyzed Benzene Arylation Incorporation of Catalytic Pivalic Acid as a Proton Shuttle. J. Am. Chem. Soc., 2006, 128, 16496-16497.
111. Lebrasseur, N.; Larrosa, I., Room Temperature and Phosphine Free Palladium Catalyzed Direct C-2 Arylation of Indoles. J. Am. Chem. Soc., 2008, 130, 2926-2927.