Transformation of step-Growth polymerization into living chain-Growth polymerization

Chemical Reviews

Volumn 116, Issue 4, 2016, Pages 1950-1958

  Yokozawa, Tsutomu ^a   Ohta, Yoshihiro ^a  

^a KANAGAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

POLYCONDENSATION; SUPRAMOLECULAR CHEMISTRY;

ADDITION-ELIMINATION; CATALYST TRANSFERS; CHAIN-GROWTH CONDENSATION POLYMERIZATIONS; CHAIN-GROWTH POLYMERIZATION; CYCLIC ADDITION; STEP-GROWTH POLYMERIZATIONS; SUBSTITUENT EFFECT; SUPRAMOLECULAR POLYMERIZATION;

LIVING POLYMERIZATION;

POLYMER;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; POLYMERIZATION; SYNTHESIS;

CATALYSIS; MOLECULAR STRUCTURE; POLYMERIZATION; POLYMERS;

EID: 84966709260     PISSN: 00092665     EISSN: 15206890     Source Type: Journal    
DOI: 10.1021/acs.chemrev.5b00393     Document Type: Review

References (163)

1. Carothers, W. H. Polymers and Polyfunctionality. Trans. Faraday Soc. 1936, 32, 39-53.
2. Flory, P. J. Molecular-Size Distribution in Linear Condensation Polymers. J. Am. Chem. Soc. 1936, 58, 1877-1885.
3. Flory, P. J. Fundamental Principles of Condensation Polymerization. Chem. Rev. 1946, 39, 137-197.
4. Lenz, R. W.; Handlovits, C. E.; Smith, H. A. Phenylene Sulfide Polymers. III. The Synthesis of Linear Poly(Phenylene Sulfide). J. Polym. Sci. 1962, 58, 351-367.
5. Newton, A. B.; Rose, J. B. Relative Reactivities of the Functional Groups Involved in Synthesis of Poly(Phenylene Ether Sulfones) from Halogenated Derivatives of Diphenyl Sulfone. Polymer 1972, 13, 465-474.
6. Lovering, J. R.; Ridd, J. H.; Parker, D. G.; Rose, J. B. Polymerization and Related Reactions Involving Nucleophilic Aromatic Substitution. Part 2. The Rates of Reaction of Substituted 4-Halobenzophenones with the Salts of Substituted Hydroquinones. J. Chem. Soc., Perkin Trans. 2 1988, 1735-1738.
7. Hibbert, D. B.; Sandall, J. P. B.; Lovering, J. R.; Ridd, J. H.; Yousaf, T. I. Polymerization and Related Reactions Involving Nucleophilic Aromatic Substitution. Part 3. Mathematical Models of the Polycondensation Reactions of Halobenzophenones. J. Chem. Soc., Perkin Trans. 2 1988, 1739-1742.
8. Robello, D. R.; Ulman, A.; Urankar, E. J. Poly(p-Phenylene Sulfone). Macromolecules 1993, 26, 6718-6721.
9. Risse, W.; Heitz, W.; Freitag, D.; Bottenbruch, L. Preparation and Characterization of Poly[Oxy(2,6-Dimethyl-1,4-Phenylene)] with Functional End Groups. Makromol. Chem. 1985, 186, 1835-1853.
10. Koch, W.; Risse, W.; Heitz, W. Radical Ions as Chain Carriers in Polymerization Reactions. Makromol. Chem. 1985, 12, 105-123.
11. Percec, V.; Wang, J. H. Phase-Transfer-Catalyzed Polymerization of 4-Bromo-2,6-Dimethylphenol in the Presence of Either 2,4,6-Trimethylphenol or 4-Tert-Butyl-2,6-Dimethylphenol. J. Polym. Sci., Part A: Polym. Chem. 1991, 29, 63-82.
12. Percec, V.; Shaffer, T. D. Functional Polymers and Sequential Copolymers by Phase-Transfer Catalysis. 23. Single Electron Transfer Phase Transfer Catalyzed Polymerization of 4-Bromo-2,6-Dimethylphenol. J. Polym. Sci., Part C: Polym. Lett. 1986, 24, 439-446.
13. Percec, V.; Wang, J. H. Synthesis of -Bis(2,6-Dimethylphenol)-Poly(2,6-Dimethyl-1,4-Phenylene Oxide) by Phase Transfer Catalyzed Polymerization of 4-Bromo-2,6-Dimethylphenol in the Presence of 2,2-Di(4-Hydroxy-3,5-Dimethylphenyl)Propane. Polym. Bull. 1990, 24, 493-500.
14. Wang, J. H.; Percec, V. Phase-Transfer Catalyzed Polymerization of 4-Bromo-2,6-Dimethylphenol in the Presence of a Terminating Comonomer Phenol: 2,4,6-Tri-Tert-Butylphenol or 4-Bromo-2,6-Di-Tert-Butylphenol. Polym. Bull. 1991, 25, 33-40.
15. Weissbach, H., Pestka, S., Eds. Molecular Mechanisms of Protein Biosynthesis; Academic Press: New York, 1977.
16. Bermek, E., Ed. Mechanisms of Protein Synthesis: Structure-Function Relations, Control Mechanisms, and Evolutionary Aspects, Proceedings of the Symposium on Molecular Mechanisms in Protein Synthesis, Istanbul, Turkey; Springer-Verlang: Berlin, 1985.
17. Kornberg, A. Biologic Synthesis of Deoxyribonucleic Acid. Science 1960, 131, 1503-1508.
18. Travers, A. Rna Polymerase Specificity and the Control of Growth. Nature 1976, 263, 641-646.
19. Yokozawa, T.; Yokoyama, A. Chain-Growth Condensation Polymerization for the Synthesis of Well-Defined Condensation Polymers and-Conjugated Polymers. Chem. Rev. 2009, 109, 5595-5619.
20. Yokozawa, T. In Polymer Science: A Comprehensive Reference; Matyjaszewski, K., Mo?ller, M., Eds.; Elsevier B.V.: Amsterdam, 2012; Vol. 5.
21. Yokozawa, T.; Ohta, Y. Scope of Controlled Synthesis Via Chain-Growth Condensation Polymerization: From Aromatic Polyamides to-Conjugated Polymers. Chem. Commun. 2013, 49, 8281-8310.
22. Yokozawa, T.; Asai, T.; Sugi, R.; Ishigooka, S.; Hiraoka, S. Chain-Growth Polycondensation for Nonbiological Polyamides of Defined Architecture. J. Am. Chem. Soc. 2000, 122, 8313-8314.
23. Yokozawa, T.; Muroya, D.; Sugi, R.; Yokoyama, A. Convenient Method of Chain-Growth Polycondensation for Well-Defined Aromatic Polyamides. Macromol. Rapid Commun. 2005, 26, 979-981.
24. Yokozawa, T.; Ogawa, M.; Sekino, A.; Sugi, R.; Yokoyama, A. Chain-Growth Polycondensation for Well-Defined Aramid. Synthesis of Unprecedented Block Copolymer Containing Aramid with Low Polydispersity. J. Am. Chem. Soc. 2002, 124, 15158-15159.
25. Yoshino, K.; Hachiman, K.; Yokoyama, A.; Yokozawa, T. Chain-Growth Condensation Polymerization of 4-Aminobenzoic Acid Esters Bearing Tri(Ethylene Glycol) Side Chain with Lithium Amide Base. J. Polym. Sci., Part A: Polym. Chem. 2010, 48, 1357-1363.
26. Ohta, Y.; Karasawa, M.; Niiyama, T.; Yokoyama, A.; Yokozawa, T. Synthesis of Well-Defined, Soluble Poly(3-Alkyl-4-Benzamide) by Chain-Growth Condensation Polymerization. J. Polym. Sci., Part A: Polym. Chem. 2014, 52, 360-365.
27. Yokoyama, A.; Iwashita, K.-I.; Hirabayashi, K.; Aiyama, K.; Yokozawa, T. Investigation of Aromatic Polyester Synthesis by the Chain-Growth Polycondensation Method. Macromolecules 2003, 36, 4328-4336.
28. Iwashita, K.; Yokoyama, A.; Yokozawa, T. Synthesis of Well-Defined Aromatic Polyesters by Chain-Growth Polycondensation under Suppression of Transesterification. J. Polym. Sci., Part A: Polym. Chem. 2005, 43, 4109-4117.
29. Yokozawa, T.; Suzuki, Y.; Hiraoka, S. Aromatic Polyethers with Low Polydispersities from Chain-Growth Polycondensation. J. Am. Chem. Soc. 2001, 123, 9902-9903.
30. Suzuki, Y.; Hiraoka, S.; Yokoyama, A.; Yokozawa, T. Chain-Growth Polycondensation for Aromatic Polyethers with Low Polydispersities: Living Polymerization Nature in Polycondensation. Macromolecules 2003, 36, 4756-4765.
31. Suzuki, Y.; Hiraoka, S.; Yokoyama, A.; Yokozawa, T. Solvent Effect on Chain-Growth Polycondensation for Aromatic Polyethers. J. Polym. Sci., Part A: Polym. Chem. 2004, 42, 1198-1207.
32. Kim, Y. J.; Seo, M.; Kim, S. Y. Synthesis of Well-Defined Rod-Coil Block Copolymers Containing Trifluoromethylated Poly-(Phenylene Oxide)s by Chain-Growth Condensation Polymerization and Atom Transfer Radical Polymerization. J. Polym. Sci., Part A: Polym. Chem. 2010, 48, 1049-1057.
33. Mikami, K.; Daikuhara, H.; Kasama, J.; Yokoyama, A.; Yokozawa, T. Synthesis of Poly(Naphthalenecarboxamide)S with Low Polydispersity by Chain-Growth Condensation Polymerization. J. Polym. Sci., Part A: Polym. Chem. 2011, 49, 3020-3029.
34. Yokozawa, T.; Taniguchi, T.; Suzuki, Y.; Yokoyama, A. Chain-Growth Polycondensation of Monomer Consisting of Two Aromatic Rings: Synthesis of Well-Defined Poly(Ether Sulfone) from 4-Fluoro-4?-Hydroxydiphenyl Sulfone. J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 3460-3464.
35. Shibasaki, Y.; Araki, T.; Nagahata, R.; Ueda, M. Control of Molecular Weight Distribution in Polycondensation Polymers 2. Poly(Ether Ketone) Synthesis. Eur. Polym. J. 2005, 41, 2428-2433.
36. Heo, J.; Kim, Y. J.; Seo, M.; Shin, S.; Kim, S. Y. Photoinduced Reversible Transmittance Modulation of Rod-Coil Type Diblock Copolymers Containing Azobenzene in the Main Chain. Chem. Commun. 2012, 48, 3351-3353.
37. Yokoyama, A.; Karasawa, M.; Taniguchi, M.; Yokozawa, T. Successive Formation of Two Amide Linkages between Two Benzene Rings. Chem. Lett. 2013, 42, 641-642.
38. Yokoyama, A.; Kawano, N.; Wada, Y.; Nishikawa, M.; Takaishi, K.; Yokozawa, T. Crystal Structure of N-Isopropylanthranilic Acid Trimer. X-Ray Struct. Anal. Online 2014, 30, 35-36.
39. Yokoyama, A.; Karasawa, M.; Kiyota, R.; Taniguchi, M.; Hirano, Y.; Ohta, Y.; Yokozawa, T. Polymerization of 4,6-Diaminoisophthalic Acid-Type Monomers Bearing Anthranilic Acid Ester and Isatoic Anhydride Moieties. Polym. J. 2015, 47, 348-351.
40. Sugi, R.; Yokoyama, A.; Furuyama, T.; Uchiyama, M.; Yokozawa, T. Inductive Effect-Assisted Chain-Growth Polycondensation. Synthetic Development from para-To meta-Substituted Aromatic Polyamides with Low Polydispersities. J. Am. Chem. Soc. 2005, 127, 10172-10173.
41. Ohishi, T.; Sugi, R.; Yokoyama, A.; Yokozawa, T. A Variety of Poly(m-benzamide)s with Low Polydispersities from Inductive Effect-Assisted Chain-Growth Polycondensation. J. Polym. Sci., Part A: Polym. Chem. 2006, 44, 4990-5003.
42. Sugi, R.; Ohishi, T.; Yokoyama, A.; Yokozawa, T. Novel Water-Soluble Poly(m-Benzamide)S: Precision Synthesis and Thermosensitivity in Aqueous Solution. Macromol. Rapid Commun. 2006, 27, 716-721.
43. Ohishi, T.; Suzuki, T.; Niiyama, T.; Mikami, K.; Yokoyama, A.; Katagiri, K.; Azumaya, I.; Yokozawa, T. Synthesis of Linear and Cyclic Aromatic Peptides with Fixed Conformation Owing to Intramolecular Hydrogen Bonding by Condensation Polymerization Method. Tetrahedron Lett. 2011, 52, 7067-7070.
44. Ohta, Y.; Niiyama, T.; Yokoyama, A.; Yokozawa, T. Chain-Growth Condensation Polymerization Approach to Synthesis of Well-Defined Polybenzoxazole: Importance of Higher Reactivity of 3-Amino-4-Hydroxybenzoic Acid Ester Compared to 4-Amino-3-Hydroxybenzoic Acid Ester. J. Polym. Sci., Part A: Polym. Chem. 2014, 52, 1730-1736.
45. Ohta, Y.; Fujii, S.; Yokoyama, A.; Furuyama, T.; Uchiyama, M.; Yokozawa, T. Synthesis of Well-Defined Hyperbranched Polyamides by Condensation Polymerization of AB2 Monomer through Changed Substituent Effects. Angew. Chem., Int. Ed. 2009, 48, 5942-5945.
46. Ohta, Y.; Kamijyo, Y.; Fujii, S.; Yokoyama, A.; Yokozawa, T. Synthesis and Properties of a Variety of Well-Defined Hyperbranched N-Alkyl and N-H Polyamides by Chain-Growth Condensation Polymerization of AB2 Monomers. Macromolecules 2011, 44, 5112-5122.
47. Ohta, Y.; Kamijyo, Y.; Yokoyama, A.; Yokozawa, T. Synthesis of Well-Defined, Water-Soluble Hyperbranched Polyamides by Chain-Growth Condensation Polymerization of AB2 Monomer. Polymers 2012, 4, 1170-1182.
48. Ohta, Y.; Yokozawa, T. Synthesis of Linear-Hyperbranched Diblock Copolymers by Means of Well-Defined Hyperbranched Polyamide Macroinitiators. Kobunshi Ronbunshu 2015, 72, 324-334.
49. Prehn, F. C.; Boyes, S. G. Surface-Initiated Chain Growth Polyaramid Brushes. Macromolecules 2015, 48, 4269-4280.
50. Tanatani, A.; Yokoyama, A.; Azumaya, I.; Takakura, Y.; Mitsui, C.; Shiro, M.; Uchiyama, M.; Muranaka, A.; Kobayashi, N.; Yokozawa, T. Helical Structures of N-Alkylated Poly(p-Benzamide)s. J. Am. Chem. Soc. 2005, 127, 8553-8561.
51. Yokoyama, A.; Inagaki, Y.; Ono, T.; Yokozawa, T. Synthesis and Helical Properties of N-Substituted p-Benzamide Random Copolymers Possessing Chiral/Achiral and (S)/(R) Side Chains. J. Polym. Sci., Part A: Polym. Chem. 2011, 49, 1387-1395.
52. Mikami, K.; Tanatani, A.; Yokoyama, A.; Yokozawa, T. Helical Folding of Poly(Naphthalenecarboxamide) Prompted by Solvophobic Effect. Macromolecules 2009, 42, 3849-3851.
53. Mikami, K.; Daikuhara, H.; Inagaki, Y.; Yokoyama, A.; Yokozawa, T. Chiral Amplification Based on Sergeants and Soldiers Effect in Helically Folded Poly(Naphthalenecarboxamide). Macromolecules 2011, 44, 3185-3188.
54. Mikami, K.; Yokozawa, T. Helical Folding of Poly-(Naphthalenecarboxamide) in Apolar Solvent. J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 739-742.
55. Yokoyama, A.; Nakano, S.; Saiki, T.; Yokozawa, T. Poly(p-Benzamide) Having Isopropyl-Substituted Chiral Tri(Ethylene Glycol) Side Chain: Synthesis and Helical Conformation. J. Polym. Sci., Part A: Polym. Chem. 2015, 53, 1379-1386.
56. McCullough, R. D.; Lowe, R. D. Enhanced Electrical Conductivity in Regioselectively Synthesized Poly(3-Alkylthiophenes). J. Chem. Soc., Chem. Commun. 1992, 70-72.
57. 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.
58. 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, 250-253.
59. 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, 4324-4333.
60. Yokoyama, A.; Miyakoshi, R.; Yokozawa, T. Chain-Growth Polymerization for Poly(3-Hexylthiophene) with a Defined Molecular Weight and a Low Polydispersity. Macromolecules 2004, 37, 1169-1171.
61. Miyakoshi, R.; Yokoyama, A.; Yokozawa, T. Synthesis of Poly(3-Hexylthiophene) with a Persity Narrower Polydispersity. Macromol. Rapid Commun. 2004, 25, 1663-1666.
62. Sheina, E. E.; Liu, J. S.; Iovu, M. C.; Laird, D. W.; McCullough, R. D. Chain Growth Mechanism for Regioregular Nickel-Initiated Cross-Coupling Polymerizations. Macromolecules 2004, 37, 3526-3528.
63. 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.
64. Miyakoshi, R.; Yokoyama, A.; Yokozawa, T. Catalyst-Transfer Polycondensation. Mechanism of Ni-Catalyzed Chain-Growth Polymerization Leading to Well-Defined Poly(3-Hexylthiophene). J. Am. Chem. Soc. 2005, 127, 17542-17547.
65. Pan, C.; Sugiyasu, K.; Aimi, J.; Sato, A.; Takeuchi, M. Picket-Fence Polythiophene and Its Diblock Copolymers That Afford Microphase Separations Comprising a Stacked and an Isolated Polythiophene Ensemble. Angew. Chem., Int. Ed. 2014, 53, 8870-8875.
66. Wu, S.; Huang, L.; Tian, H.; Geng, Y.; Wang, F. LiCl-Promoted Chain Growth Kumada Catalyst-Transfer Polycondensation of the ?Reversed? Thiophene Monomer. Macromolecules 2011, 44, 7558-7567.
67. Lamps, J. P.; Catala, J. M. Kinetic Study, by UV-Vis Spectroscopy, on the Strong Effect of LiCl on the Controlled Polymerization of 2-Bromo-3-Hexyl-5-Iodothiophene and 2-Iodo-3-Hexyl-5-Bromothiophene: Determination of the Propagation Rate Constants, Application to the Synthesis of High Molecular Weight Polydodecylthiophene. Macromolecules 2011, 44, 7962-7968.
68. Hollinger, J.; Jahnke, A. A.; Coombs, N.; Seferos, D. S. Controlling Phase Separation and Optical Properties in Conjugated Polymers through Selenophene-Thiophene Copolymerization. J. Am. Chem. Soc. 2010, 132, 8546-8547.
69. Hollinger, J.; Seferos, D. S. Morphology Control of Selenophene-Thiophene Block Copolymers through Side Chain Engineering. Macromolecules 2014, 47, 5002-5009.
70. Yokoyama, A.; Kato, A.; Miyakoshi, R.; Yokozawa, T. Precision Synthesis of Poly (N-Hexylpyrrole) and Its Diblock Copolymer with Poly(p-Phenylene) Via Catalyst-Transfer Polycondensation. Macromolecules 2008, 41, 7271-7273.
71. Miyakoshi, R.; Shimono, K.; Yokoyama, A.; Yokozawa, T. Catalyst-Transfer Polycondensation for the Synthesis of Poly(p-Phenylene) with Controlled Molecular Weight and Low Polydispersity. J. Am. Chem. Soc. 2006, 128, 16012-16013.
72. Ohshimizu, K.; Takahashi, A.; Higashihara, T.; Ueda, M. Synthesis of Poly(m-Phenylene) and Poly(m-Phenylene)-block-Poly(3-Hexylthiophene) with Low Polydispersities. J. Polym. Sci., Part A: Polym. Chem. 2011, 49, 2709-2714.
73. Sui, A.; Shi, X.; Wu, S.; Tian, H.; Geng, Y.; Wang, F. Controlled Synthesis of Polyfluorenes via Kumada Catalyst Transfer Polycondensation with Ni(acac)2/dppp as the Catalyst. Macromolecules 2012, 45, 5436-5443.
74. Willot, P.; Govaerts, S.; Koeckelberghs, G. The Controlled Polymerization of Poly(Cyclopentadithiophene)s and Their All-Conjugated Block Copolymers. Macromolecules 2013, 46, 8888-8895.
75. Boon, F.; Hergue, N.; Deshayes, G.; Moerman, D.; Desbief, S.; De Winter, J.; Gerbaux, P.; Geerts, Y. H.; Lazzaroni, R.; Dubois, P. Synthesis of Poly[(4,4[Prime or Minute]-(Dihexyl)Dithieno(3,2-b;2[Prime or Minute],3[Prime or Minute]-d)Silole)] and Copolymerization with 3-Hexylthiophene: New Semiconducting Materials with Extended Optical Absorption. Polym. Chem. 2013, 4, 4303-4307.
76. Wu, S.; Sun, Y.; Huang, L.; Wang, J.; Zhou, Y.; Geng, Y.; Wang, F. Grignard Metathesis Chain-Growth Polymerization for Poly-(Bithienylmethylene)s: Ni Catalyst Can Transfer across the Nonconjugated Monomer. Macromolecules 2010, 43, 4438-4440.
77. Nanashima, Y.; Yokoyama, A.; Yokozawa, T. Synthesis of Well-Defined Poly(2-Alkoxypyridine-3,5-diyl) via Ni-Catalyst-Transfer Condensation Polymerization. Macromolecules 2012, 45, 2609-2613.
78. Bridges, C. R.; McCormick, T. M.; Gibson, G. L.; Hollinger, J.; Seferos, D. S. Designing and Refining Ni(II)Diimine Catalysts toward the Controlled Synthesis of Electron-Deficient Conjugated Polymers. J. Am. Chem. Soc. 2013, 135, 13212-13219.
79. Pammer, F.; Passlack, U. Head-To-Tail Regioregular Polythiazole Prepared via Kumada-Coupling Polycondensation. ACS Macro Lett. 2014, 3, 170-174.
80. Pammer, F.; Ja?ger, J.; Rudolf, B.; Sun, Y. Soluble Head-To-Tail Regioregular Polythiazoles: Preparation, Properties, and Evidence for Chain-Growth Behavior in the Synthesis Via Kumada-Coupling Polycondensation. Macromolecules 2014, 47, 5904-5912.
81. Ono, R. J.; Kang, S.; Bielawski, C. W. Controlled Chain-Growth Kumada Catalyst Transfer Polycondensation of a Conjugated Alternating Copolymer. Macromolecules 2012, 45, 2321-2326.
82. Willot, P.; Koeckelberghs, G. Evidence for Catalyst Association in the Catalyst Transfer Polymerization of Thieno[3,2-b]Thiophene. Macromolecules 2014, 47, 8548-8555.
83. Nojima, M.; Ohta, Y.; Yokozawa, T. Investigation of Catalyst-Transfer Condensation Polymerization for Synthesis of Poly(p-Phenylenevinylene). J. Polym. Sci., Part A: Polym. Chem. 2014, 52, 2643-2653.
84. Verswyvel, M.; Hoebers, C.; De Winter, J.; Gerbaux, P.; Koeckelberghs, G. Study of the Controlled Chain-Growth Polymerization of Poly(3,6-Phenanthrene). J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 5067-5074.
85. Yokozawa, T.; Suzuki, R.; Nojima, M.; Ohta, Y.; Yokoyama, A. Precision Synthesis of Poly(3-Hexylthiophene) from Catalyst-Transfer Suzuki-Miyaura Coupling Polymerization. Macromol. Rapid Commun. 2011, 32, 801-806.
86. Sui, A.; Shi, X.; Tian, H.; Geng, Y.; Wang, F. Suzuki-Miyaura Catalyst-Transfer Polycondensation with Pd(IPr) (OAc)2 as the Catalyst for the Controlled Synthesis of Polyfluorenes and Polythiophenes. Polym. Chem. 2014, 5, 7072-7080.
87. Kosaka, K.; Ohta, Y.; Yokozawa, T. Influence of the Boron Moiety and Water on Suzuki-Miyaura Catalyst-Transfer Condensation Polymerization. Macromol. Rapid Commun. 2015, 36, 373-377.
88. Yokozawa, T.; Kohno, H.; Ohta, Y.; Yokoyama, A. Catalyst-Transfer Suzuki-Miyaura Coupling Polymerization for Precision Synthesis of Poly(p-Phenylene). Macromolecules 2010, 43, 7095-7100.
89. Yokoyama, A.; Suzuki, H.; Kubota, Y.; Ohuchi, K.; Higashimura, H.; Yokozawa, T. Chain-Growth Polymerization for the Synthesis of Polyfluorene via Suzuki-Miyaura Coupling Reaction from an Externally Added Initiator Unit. J. Am. Chem. Soc. 2007, 129, 7236-7237.
90. Elmalem, E.; Kiriy, A.; Huck, W. T. S. Chain-Growth Suzuki Polymerization of n-Type Fluorene Copolymers. Macromolecules 2011, 44, 9057-9061.
91. Nojima, M.; Ohta, Y.; Yokozawa, T. Structural Requirements for Palladium Catalyst Transfer on a Carbon-Carbon Double Bond. J. Am. Chem. Soc. 2015, 137, 5682-5685.
92. Higashihara, T.; Goto, E.; Ueda, M. Purification-Free and Protection-Free Synthesis of Regioregular Poly(3-Hexylthiophene) and Poly(3-(6-Hydroxyhexyl)Thiophene) Using a Zincate Complex of tBu4ZnLi2. ACS Macro Lett. 2012, 1, 167-170.
93. Qiu, Y.; Mohin, J.; Tsai, C.-H.; Tristram-Nagle, S.; Gil, R. R.; Kowalewski, T.; Noonan, K. J. T. Stille Catalyst-Transfer Polycondensation Using Pd-PEPPSI-IPr for High-Molecular-Weight Regioregular Poly(3-Hexylthiophene). Macromol. Rapid Commun. 2015, 36, 840-844.
94. Tkachov, R.; Senkovskyy, V.; Beryozkina, T.; Boyko, K.; Bakulev, V.; Lederer, A.; Sahre, K.; Voit, B.; Kiriy, A. Palladium-Catalyzed Chain-Growth Polycondensation of AB-Type Monomers: High Catalyst Turnover and Polymerization Rates. Angew. Chem., Int. Ed. 2014, 53, 2402-2407.
95. Erdmann, T.; Back, J.; Tkachov, R.; Ruff, A.; Voit, B.; Ludwigs, S.; Kiriy, A. Dithienosilole-Based All-Conjugated Block Copolymers Synthesized by a Combination of Quasi-Living Kumada and Negishi Catalyst-Transfer Polycondensations. Polym. Chem. 2014, 5, 5383-5390.
96. Senkovskyy, V.; Tkachov, R.; Komber, H.; Sommer, M.; Heuken, M.; Voit, B.; Huck, W. T. S.; Kataev, V.; Petr, A.; Kiriy, A. Chain-Growth Polymerization of Unusual Anion-Radical Monomers Based on Naphthalene Diimide: A New Route to Well-Defined n-Type Conjugated Copolymers. J. Am. Chem. Soc. 2011, 133, 19966-19970.
97. Senkovskyy, V.; Tkachov, R.; Komber, H.; John, A.; Sommer, J.-U.; Kiriy, A. Mechanistic Insight into Catalyst-Transfer Polymerization of Unusual Anion-Radical Naphthalene Diimide Monomers: An Observation of Ni(0) Intermediates. Macromolecules 2012, 45, 7770-7777.
98. Tkachov, R.; Karpov, Y.; Senkovskyy, V.; Raguzin, I.; Zessin, J.; Lederer, A.; Stamm, M.; Voit, B.; Beryozkina, T.; Bakulev, V.; Zhao, W.; Facchetti, A.; Kiriy, A. Efficient Tin-Free Route to a Donor-Acceptor Semiconducting Copolymer with Variable Molecular Weights. Macromolecules 2014, 47, 3845-3851.
99. Liu, W.; Tkachov, R.; Komber, H.; Senkovskyy, V.; Schubert, M.; Wei, Z.; Facchetti, A.; Neher, D.; Kiriy, A. Chain-Growth Polycondensation of Perylene Diimide-Based Copolymers: A New Route to Regio-Regular Perylene Diimide-Based Acceptors for All-Polymer Solar Cells and n-Type Transistors. Polym. Chem. 2014, 5, 3404-3411.
100. Kang, S.; Ono, R. J.; Bielawski, C. W. Controlled Catalyst Transfer Polycondensation and Surface-Initiated Polymerization of a p-Phenyleneethynylene-Based Monomer. J. Am. Chem. Soc. 2013, 135, 4984-4987.
101. Nojima, M.; Saito, R.; Ohta, Y.; Yokozawa, T. Investigation of Mizoroki-Heck Coupling Polymerization as a Catalyst-Transfer Condensation Polymerization for Synthesis of Poly(p-Phenylenevinylene). J. Polym. Sci., Part A: Polym. Chem. 2015, 53, 543-551.
102. Littke, A. F.; Fu, G. C. A Versatile Catalyst for Heck Reactions of Aryl Chlorides and Aryl Bromides under Mild Conditions. J. Am. Chem. Soc. 2001, 123, 6989-7000.
103. Sanji, T.; Iyoda, T. Transition-Metal-Free Controlled Polymerization of 2-Perfluoroaryl-5-Trimethylsilylthiophenes. J. Am. Chem. Soc. 2014, 136, 10238-10241.
104. Sanji, T.; Motoshige, A.; Komiyama, H.; Kakinuma, J.; Ushikubo, R.; Watanabe, S.; Iyoda, T. Transition-Metal-Free Controlled Polymerization for Poly(p-Aryleneethynylene)s. Chem. Sci. 2015, 6, 492-496.
105. Tkachov, R.; Senkovskyy, V.; Komber, H.; Sommer, J.-U.; Kiriy, A. Random Catalyst Walking Along Polymerized Poly(3-Hexylthiophene) Chains in Kumada Catalyst-Transfer Polycondensation. J. Am. Chem. Soc. 2010, 132, 7803-7810.
106. Kohn, P.; Huettner, S.; Komber, H.; Senkovskyy, V.; Tkachov, R.; Kiriy, A.; Friend, R. H.; Steiner, U.; Huck, W. T. S.; Sommer, J.-U.; Sommer, M. On the Role of Single Regiodefects and Polydispersity in Regioregular Poly(3-Hexylthiophene): Defect Distribution, Synthesis of Defect-Free Chains, and a Simple Model for the Determination of Crystallinity. J. Am. Chem. Soc. 2012, 134, 4790-4805.
107. Verswyvel, M.; Monnaie, F.; Koeckelberghs, G. AB Block Copoly(3-Alkylthiophenes): Synthesis and Chiroptical Behavior. Macromolecules 2011, 44, 9489-9498.
108. Willot, P.; Teyssandier, J.; Dujardin, W.; Adisoejoso, J.; De Feyter, S.; Moerman, D.; Leclere, P.; Lazzaroni, R.; Koeckelberghs, G. Direct Visualization of Microphase Separation in Block Copoly(3-Alkylthiophene)S. RSC Adv. 2015, 5, 8721-8726.
109. Verswyvel, M.; Verstappen, P.; De Cremer, L.; Verbiest, T.; Koeckelberghs, G. Development of a Universal Chain-Growth Polymerization Protocol of Conjugated Polymers: Toward a Variety of All-Conjugated Block-Copolymers. J. Polym. Sci., Part A: Polym. Chem. 2011, 49, 5339-5349.
110. Jeffries-El, M.; Sauve, G.; McCullough, R. D. Facile Synthesis of End-Functionalized Regioregular Poly(3-Alkylthiophene)s Via Modified Grignard Metathesis Reaction. Macromolecules 2005, 38, 10346-10352.
111. Takahashi, A.; Rho, Y.; Higashihara, T.; Ahn, B.; Ree, M.; Ueda, M. Preparation of Nanoporous Poly(3-Hexylthiophene) Films Based on a Template System of Block Copolymers via Ionic Interaction. Macromolecules 2010, 43, 4843-4852.
112. Fujita, H.; Michinobu, T.; Tokita, M.; Ueda, M.; Higashihara, T. Synthesis and Postfunctionalization of Rod-Coil Diblock and Coil-Rod-Coil Triblock Copolymers Composed of Poly(3-Hexylthiophene) and Poly(4-(4?-N,N-Dihexylaminophenylethynyl)Styrene) Segments. Macromolecules 2012, 45, 9643-9656.
113. Handa, N. V.; Serrano, A. V.; Robb, M. J.; Hawker, C. J. Exploring the Synthesis and Impact of End-Functional Poly(3-Hexylthiophene). J. Polym. Sci., Part A: Polym. Chem. 2015, 53, 831-841.
114. Bronstein, H. A.; Luscombe, C. K. Externally Initiated Regioregular P3HT with Controlled Molecular Weight and Narrow Polydispersity. J. Am. Chem. Soc. 2009, 131, 12894-12895.
115. Smeets, A.; Van den Bergh, K.; De Winter, J.; Gerbaux, P.; Verbiest, T.; Koeckelberghs, G. Incorporation of Different End Groups in Conjugated Polymers Using Functional Nickel Initiators. Macromolecules 2009, 42, 7638-7641.
116. Senkovskyy, V.; Tkachov, R.; Beryozkina, T.; Komber, H.; Oertel, U.; Horecha, M.; Bocharova, V.; Stamm, M.; Gevorgyan, S. A.; Krebs, F. C.; Kiriy, A. ?Hairy? Poly(3-Hexylthiophene) Particles Prepared via Surface-Initiated Kumada Catalyst-Transfer Polycondensation. J. Am. Chem. Soc. 2009, 131, 16445-16453.
117. Kaul, E.; Senkovskyy, V.; Tkachov, R.; Bocharova, V.; Komber, H.; Stamm, M.; Kiriy, A. Synthesis of a Bifunctional Initiator for Controlled Kumada Catalyst-Transfer Polycondensation/Nitroxide-Mediated Polymerization and Preparation of Poly(3-Hexylthiophene)-Polystyrene Block Copolymer Therefrom. Macromolecules 2010, 43, 77-81.
118. Senkovskyy, V.; Sommer, M.; Tkachov, R.; Komber, H.; Huck, W. T. S.; Kiriy, A. Convenient Route to Initiate Kumada Catalyst-Transfer Polycondensation Using Ni(dppe)Cl2 or Ni(dppp)Cl2 and Sterically Hindered Grignard Compounds. Macromolecules 2010, 43, 10157-10161.
119. Gutacker, A.; Lin, C.-Y.; Ying, L.; Nguyen, T.-Q.; Scherf, U.; Bazan, G. C. Cationic Polyfluorene-B-Neutral Polyfluorene ?Rod-Rod? Diblock Copolymers. Macromolecules 2012, 45, 4441-4446.
120. Stambuli, J. P.; Incarvito, C. D.; Buhl, M.; Hartwig, J. F. Synthesis, Structure, Theoretical Studies, and Ligand Exchange Reactions of Monomeric, T-Shaped Arylpalladium(II) Halide Complexes with an Additional, Weak Agostic Interaction. J. Am. Chem. Soc. 2004, 126, 1184-1194.
121. Nanashima, Y.; Shibata, R.; Miyakoshi, R.; Yokoyama, A.; Yokozawa, T. Investigation of Catalyst-Transfer Condensation Polymerization for the Synthesis of n-Type-Conjugated Polymer, Poly(2-Dioxaalkylpyridine-3,6-diyl). J. Polym. Sci., Part A: Polym. Chem. 2012, 50, 3628-3640.
122. Lee, J. K.; Ko, S.; Bao, Z. In Situ Hetero End-Functionalized Polythiophene and Subsequent "Click" Chemistry with DNA. Macromol. Rapid Commun. 2012, 33, 938-942.
123. Elmalem, E.; Biedermann, F.; Johnson, K.; Friend, R. H.; Huck, W. T. S. Synthesis and Photophysics of Fully-Conjugated Heterobis-Functionalized Polymeric Molecular Wires via Suzuki Chain-Growth Polymerization. J. Am. Chem. Soc. 2012, 134, 17769-17777.
124. Fischer, C. S.; Baier, M. C.; Mecking, S. Enhanced Brightness Emission-Tuned Nanoparticles from Heterodifunctional Polyfluorene Building Blocks. J. Am. Chem. Soc. 2013, 135, 1148-1154.
125. Zhang, Z.; Hu, P.; Li, X.; Zhan, H.; Cheng, Y. Investigation of Suzuki-Miyaura Catalyst-Transfer Polycondensation of AB-Type Fluorene Monomer Using Coordination-Saturated Aryl Pd(II) Halide Complexes as Initiators. J. Polym. Sci., Part A: Polym. Chem. 2015, 53, 1457-1463.
126. Zhang, H.-H.; Xing, C.-H.; Hu, Q.-S. Controlled Pd(0)/t-Bu3PCatalyzed Suzuki Cross-Coupling Polymerization of AB-Type Monomers with PhPd(t-Bu3P)I or Pd2(dba)3/t-Bu3P/ArI as the Initiator. J. Am. Chem. Soc. 2012, 134, 13156-13159.
127. Zhang, H.-H.; Xing, C.-H.; Hu, Q.-S.; Hong, K. Controlled Pd(0)/t-Bu3P-Catalyzed Suzuki Cross-Coupling Polymerization of ABType Monomers with ArPd(t-Bu3P)X or Pd2(dba)3/t-Bu3P/ArX as the Initiator. Macromolecules 2015, 48, 967-978.
128. Yokozawa, T. In Conjugated Polymer Synthesis; Chujo, Y., Ed.; Wiley-VCH: Weinheim, Germany, 2010.
129. Osaka, I.; McCullough, R. D. In Conjugated Polymer Synthesis; Chujo, Y., Ed.; Wiley-VCH: Weinheim, Germany, 2010.
130. Kiriy, A.; Senkovskyy, V.; Sommer, M. Kumada Catalyst-Transfer Polycondensation: Mechanism, Opportunities, and Challenges. Macromol. Rapid Commun. 2011, 32, 1503-1517.
131. Stefan, M. C.; Bhatt, M. P.; Sista, P.; Magurudeniya, H. D. Grignard Metathesis (GRIM) Polymerization for the Synthesis of Conjugated Block Copolymers Containing Regioregular Poly(3-Hexylthiophene). Polym. Chem. 2012, 3, 1693-1701.
132. Bryan, Z. J.; McNeil, A. J. Conjugated Polymer Synthesis via Catalyst-Transfer Polycondensation (CTP): Mechanism, Scope, and Applications. Macromolecules 2013, 46, 8395-8405.
133. Wang, J.; Higashihara, T. Synthesis of All-Conjugated Donor-Acceptor Block Copolymers and Their Application in All-Polymer Solar Cells. Polym. Chem. 2013, 4, 5518-5526.
134. Hollinger, J.; DiCarmine, P. M.; Karl, D.; Seferos, D. S. Heterocycle-Induced Phase Separation in Conjugated Polymers. Macromolecules 2012, 45, 3772-3778.
135. Palermo, E. F.; McNeil, A. J. Impact of Copolymer Sequence on Solid-State Properties for Random, Gradient and Block Copolymers Containing Thiophene and Selenophene. Macromolecules 2012, 45, 5948-5955.
136. Hollinger, J.; Sun, J.; Gao, D.; Karl, D.; Seferos, D. S. Statistical Conjugated Polymers Comprising Optoelectronically Distinct Units. Macromol. Rapid Commun. 2013, 34, 437-441.
137. Miyakoshi, R.; Yokoyama, A.; Yokozawa, T. Importance of the Order of Successive Catalyst-Transfer Condensation Polymerization in the Synthesis of Block Copolymers of Polythiophene and Poly(p-Phenylene). Chem. Lett. 2008, 37, 1022-1023.
138. Wu, S.; Bu, L.; Huang, L.; Yu, X.; Han, Y.; Geng, Y.; Wang, F. Synthesis and Characterization of Phenylene-Thiophene All-Conjugated Diblock Copolymers. Polymer 2009, 50, 6245-6251.
139. Yu, X.; Yang, H.; Wu, S.; Geng, Y.; Han, Y. Microphase Separation and Crystallization of All-Conjugated Phenylene-Thiophene Diblock Copolymers. Macromolecules 2012, 45, 266-274.
140. Lee, Y.-H.; Chen, W.-C.; Yang, Y.-L.; Chiang, C.-J.; Yokozawa, T.; Dai, C.-A. Co-Crystallization Phase Transformations in All-Conjugated Block Copolymers with Different Main-Chain Moieties. Nanoscale 2014, 6, 5208-5216.
141. Lee, Y.-H.; Lee, Y.-P.; Chiang, C.-J.; Wei, F.-K.; Wu, C.-H.; Chen, W.-C.; Shen, C.; Jeng, H.-A.; Wang, L.; Liu, M.-W.; Chen, Y.-F.; Yokozawa, T.; Dai, C.-A. A New Strategy for Co-Assembling-Conjugated Polymer/Cadmium Sulfide Hybrids into an Efficient Charge-Transporting Nanochannel Array by Using an All-Conjugated Diblock Copolymer Motif. J. Mater. Chem. A 2014, 2, 14600-14612.
142. Willot, P.; Moerman, D.; Lecle?re, P.; Lazzaroni, R.; Baeten, Y.; Van der Auweraer, M.; Koeckelberghs, G. One-Pot Synthesis and Characterization of All-Conjugated Poly(3-Alkylthiophene)-Block-Poly(Dialkylthieno[3,4-b]Pyrazine). Macromolecules 2014, 47, 6671-6678.
143. Verswyvel, M.; Steverlynck, J.; Hadj Mohamed, S.; Trabelsi, M.; Champagne, B.; Koeckelberghs, G. All-Conjugated ABC-Block-Copolymer Formation with a Varying Sequence via an Unassociated Catalyst. Macromolecules 2014, 47, 4668-4675.
144. Monnaie, F.; Ceunen, W.; De Winter, J.; Gerbaux, P.; Cocchi, V.; Salatelli, E.; Koeckelberghs, G. Synthesis and Transfer of Chirality in Supramolecular Hydrogen Bonded Conjugated Diblock Copolymers. Macromolecules 2015, 48, 90-98.
145. Bridges, C. R.; Yan, H.; Pollit, A. A.; Seferos, D. S. Controlled Synthesis of Fully-Conjugated Donor-Acceptor Block Copolymers Using a Ni(II) Diimine Catalyst. ACS Macro Lett. 2014, 3, 671-674.
146. Willot, P.; Steverlynck, J.; Moerman, D.; Leclere, P.; Lazzaroni, R.; Koeckelberghs, G. Poly(3-Alkylthiophene) with Tuneable Regioregularity: Synthesis and Self-Assembling Properties. Polym. Chem. 2013, 4, 2662-2671.
147. Yang, Y.-L.; Lee, Y.-H.; Lee, Y.-P.; Chiang, C.-J.; Shen, C.; Wu, C.-C.; Ohta, Y.; Yokozawa, T.; Dai, C.-A. Synthesis and Characterization of Poly(3-Hexylthiophene)-Poly(3-Hexyloxythiophene) Random Copolymers with Tunable Band Gap via Grignard Metathesis Polymerization. Polym. Int. 2014, 63, 2068-2075.
148. Kozycz, L. M.; Gao, D.; Seferos, D. S. Compositional Influence on the Regioregularity and Device Parameters of a Conjugated Statistical Copolymer. Macromolecules 2013, 46, 613-621.
149. Hardeman, T.; Koeckelberghs, G. Steering Poly(Thiophene) Properties by Incorporation of Phenyl Groups. Macromolecules 2014, 47, 8618-8624.
150. Pollit, A. A.; Bridges, C. R.; Seferos, D. S. Evidence for the Chain-Growth Synthesis of Statistical-Conjugated Donor-Acceptor Copolymers. Macromol. Rapid Commun. 2015, 36, 65-70.
151. Tkachov, R.; Komber, H.; Rauch, S.; Lederer, A.; Oertel, U.; Ha?ußler, L.; Voit, B.; Kiriy, A. One-Pot Synthesis of All-Conjugated Block-Like Bisthiophene-Naphthalenediimide/Fluorene Copolymer. Macromolecules 2014, 47, 4994-5001.
152. Yuan, M.; Okamoto, K.; Bronstein, H. A.; Luscombe, C. K. Constructing Regioregular Star Poly(3-Hexylthiophene) via Externally Initiated Kumada Catalyst-Transfer Polycondensation. ACS Macro Lett. 2012, 1, 392-395.
153. Fischer, C. S.; Jenewein, C.; Mecking, S. Conjugated Star Polymers from Multidirectional Suzuki-Miyaura Polymerization for Live Cell Imaging. Macromolecules 2015, 48, 483-491.
154. Wang, J.; Lu, C.; Mizobe, T.; Ueda, M.; Chen, W.-C.; Higashihara, T. Synthesis and Characterization of All-Conjugated Graft Copolymers Comprised of n-Type or p-Type Backbones and Poly(3-Hexylthiophene) Side Chains. Macromolecules 2013, 46, 1783-1793.
155. Lim, H.; Chao, C.-Y.; Su, W.-F. Modulating Crystallinity of Poly(3-Hexylthiophene) via Microphase Separation of Poly(3-Hexylthiophene)-Polyisoprene Block Copolymers. Macromolecules 2015, 48, 3269-3281.
156. Hardeman, T.; Willot, P.; Winter, J. D.; Josse, T.; Gerbaux, P.; Shestakova, P.; Nies, E.; Koeckelberghs, G. Study on the Formation of a Supramolecular Conjugated Graft Copolymer in Solution. J. Polym. Sci., Part A: Polym. Chem. 2014, 52, 804-809.
157. Pentzer, E. B.; Bokel, F. A.; Hayward, R. C.; Emrick, T. Nanocomposite "Superhighways" by Solution Assembly of Semiconductor Nanostructures with Ligand-Functionalized Conjugated Polymers. Adv. Mater. 2012, 24, 2254-2258.
158. Monnaie, F.; Brullot, W.; Verbiest, T.; De Winter, J.; Gerbaux, P.; Smeets, A.; Koeckelberghs, G. Synthesis of End-Group Functionalized P3HT: General Protocol for P3HT/Nanoparticle Hybrids. Macromolecules 2013, 46, 8500-8508.
159. Gao, L.-M.; Hu, Y.-Y.; Yu, Z.-P.; Liu, N.; Yin, J.; Zhu, Y.-Y.; Ding, Y.; Wu, Z.-Q. Facile Preparation of Regioregular Poly(3-Hexylthiophene) and Its Block Copolymers with-Allylnickel Complex as External Initiator. Macromolecules 2014, 47, 5010-5018.
160. Sugiura, T.; Yajima, D.; Shoji, K.; Ohta, Y.; Yokozawa, T. Control of Chain Ends of Polyesters in Polycondensation of AA and BB Monomers by Use of Solid-Phase Reagent. J. Polym. Sci., Part A: Polym. Chem. 2015, 53, 1623-1628.
161. Ogi, S.; Sugiyasu, K.; Manna, S.; Samitsu, S.; Takeuchi, M. Living Supramolecular Polymerization Realized through a Biomimetic Approach. Nat. Chem. 2014, 6, 188-195.
162. Kang, J.; Miyajima, D.; Mori, T.; Inoue, Y.; Itoh, Y.; Aida, T. A Rational Strategy for the Realization of Chain-Growth Supramolecular Polymerization. Science 2015, 347, 646-651.
163. Sugiyama, Y.; Kato, R.; Sakurada, T.; Okamoto, S. Chain-Growth Cycloaddition Polymerization via a Catalytic Alkyne [2 + 2 + 2] Cyclotrimerization Reaction and Its Application to One-Shot Spontaneous Block Copolymerization. J. Am. Chem. Soc. 2011, 133, 9712-9715.