Insights in the Ni-thiophene association in the synthesis of thiophene-para-phenylene block copolymers via Kumada catalyst transfer condensative polymerization
Ceunen, Ward; De Winter, Julien; Gerbaux, Pascalet al.
2019 • In European Polymer Journal, 121, p. 109311
CIRMAP - Centre d'Innovation et de Recherche en Matériaux Polymères CISMA - Centre Interdisciplinaire de Spectrométrie de Masse
Disciplines :
Architecture Chemistry
Author, co-author :
Ceunen, Ward
De Winter, Julien ; Université de Mons > Faculté des Sciences > Service de Synthèse et spectrométrie de masse organiques
Gerbaux, Pascal ; Université de Mons > Faculté des Sciences > Service de Synthèse et spectrométrie de masse organiques
Koeckelberghs, Guy
Language :
English
Title :
Insights in the Ni-thiophene association in the synthesis of thiophene-para-phenylene block copolymers via Kumada catalyst transfer condensative polymerization
Publication date :
07 January 2019
Journal title :
European Polymer Journal
ISSN :
0014-3057
eISSN :
1873-1945
Publisher :
Elsevier, United Kingdom
Volume :
121
Pages :
109311
Peer reviewed :
Peer Reviewed verified by ORBi
Research unit :
S836 - Synthèse et spectrométrie de masse organiques
Research institute :
R400 - Institut de Recherche en Science et Ingénierie des Matériaux R100 - Institut des Biosciences
Beaujuge, P. M.; Fréchet, J. M. J. Molecular Design and Ordering Effects in π-Functional Materials for Transistor and Solar Cell Applications. J. Am. Chem. Soc. 2011, 133 (50), 20009–20029 DOI: 10.1021/ja2073643.
Organic Light-Emitting Devices; Shinar, J., Ed.; Springer New York: New York, NY, 2004.
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 DOI: 10.1021/cr900182s.
Grimsdale, A. C.; Leok Chan, K.; Martin, R. E.; Jokisz, P. G.; Holmes, A. B. Synthesis of Light-Emitting Conjugated Polymers for Applications in Electroluminescent Devices. Chem. Rev. 2009, 109 (3), 897–1091 DOI: 10.1021/cr000013v.
Roberts, M. E.; Sokolov, A. N.; Bao, Z. Material and Device Considerations for Organic Thin-Film Transistor Sensors. J. Mater. Chem. 2009, 19 (21), 3351–3363 DOI: 10.1039/b816386c.
Handbook of Thiophene-Based Materials; Perepichka, I. F., Perepichka, D. F., Eds.; John Wiley & Sons, Ltd: Chichester, UK, 2009.
Someya, T.; Dodabalapur, A.; Huang, J.; See, K. C.; Katz, H. E. Chemical and Physical Sensing by Organic Field-Effect Transistors and Related Devices. Adv. Mater. 2010, 22 (34), 3799–3811 DOI: 10.1002/adma.200902760.
Boudreault, P. L. T.; Najari, A.; Leclerc, M. Processable Low-Bandgap Polymers for Photovoltaic Applications. Chem. Mater. 2011, 23 (3), 456–469 DOI: 10.1021/cm1021855.
Facchetti, A. π-Conjugated Polymers for Organic Electronics and Photovoltaic Cell Applications. Chem. Mater. 2011, 23 (3), 733–758 DOI: 10.1021/cm102419z.
Lin, P.; Yan, F. Organic Thin-Film Transistors for Chemical and Biological Sensing. Adv. Mater. 2012, 24 (1), 34–51 DOI: 10.1002/adma.201103334.
Zhou, H.; Yang, L.; You, W. Rational Design of High Performance Conjugated Polymers for Organic Solar Cells. Macromolecules 2012, 45 (2), 607–632 DOI: 10.1021/ma201648t.
Han, W.; He, M.; Byun, M.; Li, B.; Lin, Z. Large-Scale Hierarchically Structured Conjugated Polymer Assemblies with Enhanced Electrical Conductivity. Angew. Chemie - Int. Ed. 2013, 52 (9), 2564–2568 DOI: 10.1002/anie.201209632.
Mei, J.; Diao, Y.; Appleton, A. L.; Fang, L.; Bao, Z. Integrated Materials Design of Organic Semiconductors for Field-Effect Transistors. J. Am. Chem. Soc. 2013, 135 (18), 6724–6746 DOI: 10.1021/ja400881n.
Jung, J.; Yoon, Y. J.; He, M.; Lin, Z. Organic-Inorganic Nanocomposites Composed of Conjugated Polymers and Semiconductor Nanocrystals for Photovoltaics. J. Polym. Sci. Part B Polym. Phys. 2014, 52 (24), 1641–1660 DOI: 10.1002/polb.23612.
Lu, L.; Zheng, T.; Wu, Q.; Schneider, A. M.; Zhao, D.; Yu, L. Recent Advances in Bulk Heterojunction Polymer Solar Cells. Chem. Rev. 2015, 115 (23), 12666–12731 DOI: 10.1021/acs.chemrev.5b00098.
Huynh, T. P.; Sharma, P. S.; Sosnowska, M.; D'Souza, F.; Kutner, W. Functionalized Polythiophenes: Recognition Materials for Chemosensors and Biosensors of Superior Sensitivity, Selectivity, and Detectability. Prog. Polym. Sci. 2015, 47, 1–25 DOI: 10.1016/j.progpolymsci.2015.04.009.
Li, G.; Chang, W. H.; Yang, Y. Low-Bandgap Conjugated Polymers Enabling Solution-Processable Tandem Solar Cells. Nat. Rev. Mater. 2017, 2 (8), 1–13 DOI: 10.1038/natrevmats.2017.43.
McQuade, D. T.; Pullen, A. E.; Swager, T. M. Conjugated Polymer-Based Chemical Sensors. Chem. Rev. 2000, 100 (7), 2537–2574 DOI: 10.1021/cr9801014.
Verheyen, L.; Leysen, P.; Van Den Eede, M.-P.; Ceunen, W.; Hardeman, T.; Koeckelberghs, G. Advances in the Controlled Polymerization of Conjugated Polymers. Polymer (Guildf). 2017, 108, 521–546 DOI: 10.1016/j.polymer.2016.09.085.
Salleo, A.; Kline, R. J.; DeLongchamp, D. M.; Chabinyc, M. L. Microstructural Characterization and Charge Transport in Thin Films of Conjugated Polymers. Adv. Mater. 2010, 22 (34), 3812–3838 DOI: 10.1002/adma.200903712.
Vakhshouri, K.; Kozub, D. R.; Wang, C.; Salleo, A.; Gomez, E. D. Effect of Miscibility and Percolation on Electron Transport in Amorphous Poly(3-Hexylthiophene)/Phenyl-C 61-Butyric Acid Methyl Ester Blends. Phys. Rev. Lett. 2012, 108 (2) DOI: 10.1103/PhysRevLett.108.026601.
Günes, S.; Neugebauer, H.; Sariciftci, N. S. Conjugated Polymer-Based Organic Solar Cells. Chem. Rev. 2007, 107 (4), 1324–1338 DOI: 10.1021/cr050149z.
Dang, M. T.; Hirsch, L.; Wantz, G. P3HT:PCBM, Best Seller in Polymer Photovoltaic Research. Adv. Mater. 2011, 23 (31), 3597–3602 DOI: 10.1002/adma.201100792.
P. Sista, C.K. Luscombe, Progress in the Synthesis of Poly (3-Hexylthiophene), 2014, pp 1–38.
Marrocchi, A.; Lanari, D.; Facchetti, A.; Vaccaro, L. Poly(3-Hexylthiophene): Synthetic Methodologies and Properties in Bulk Heterojunction Solar Cells. Energy Environ. Sci. 2012, 5 (9), 8457 DOI: 10.1039/c2ee22129b.
Vangerven, T.; Verstappen, P.; Drijkoningen, J.; Dierckx, W.; Himmelberger, S.; Salleo, A.; Vanderzande, D.; Maes, W.; Manca, J. V. Molar Mass versus Polymer Solar Cell Performance: Highlighting the Role of Homocouplings. Chem. Mater. 2015, 27 (10), 3726–3732 DOI: 10.1021/acs.chemmater.5b00939.
Aplan, M. P.; Gomez, E. D. Recent Developments in Chain-Growth Polymerizations of Conjugated Polymers. Ind. Eng. Chem. Res. 2017, 56 (28), 7888–7901 DOI: 10.1021/acs.iecr.7b01030.
Yokozawa, T.; Ohta, Y. Transformation of Step-Growth Polymerization into Living Chain-Growth Polymerization. Chem. Rev. 2016, 116 (4), 1950–1968 DOI: 10.1021/acs.chemrev.5b00393.
Lee, C.; Lee, S.; Kim, G.-U.; Lee, W.; Kim, B. J. Recent Advances, Design Guidelines, and Prospects of All-Polymer Solar Cells. Chem. Rev. 2019, 119 (13), 8028–8086 DOI: 10.1021/acs.chemrev.9b00044.
Wang, J.; Higashihara, T. Synthesis of All-Conjugated Donor–Acceptor Block Copolymers and Their Application in All-Polymer Solar Cells. Polym. Chem. 2013, 4 (22), 5518 DOI: 10.1039/c3py00979c.
Bryan, Z. J.; McNeil, A. J. Conjugated Polymer Synthesis via Catalyst-Transfer Polycondensation (CTP): Mechanism, Scope, and Applications. Macromolecules 2013, 46 (21), 8395–8405 DOI: 10.1021/ma401314x.
McCullough, R. D.; Spectus, C. O. N.; Osaka, I.; McCullough, R. D. Advances in Molecular Design and Synthesis of Regioregular Polythiophenes. Acc. Chem. Res. 2008, 41 (9), 1202–1214 DOI: 10.1021/ar800130s.
Design and Synthesis of Conjugated Polymers; Leclerc, M., Morin, J.-F., Eds.; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2010.
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 (10), 1022–1023 DOI: 10.1246/cl.2008.1022.
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 (50), 16012–16013 DOI: 10.1021/ja067107s.
Ono, R. J.; Kang, S.; Bielawski, C. W. Controlled Chain-Growth Kumada Catalyst Transfer Polycondensation of a Conjugated Alternating Copolymer. Macromolecules 2012, 45 (5), 2321–2326 DOI: 10.1021/ma300013e.
Mikami, K.; Nojima, M.; Masumoto, Y.; Mizukoshi, Y.; Takita, R.; Yokozawa, T.; Uchiyama, M. Catalyst-Dependent Intrinsic Ring-Walking Behavior on π-Face of Conjugated Polymers. Polym. Chem. 2017, 8 (10), 1708–1713 DOI: 10.1039/c6py01934j.
Bahri-Laleh, N.; Poater, A.; Cavallo, L.; Mirmohammadi, S. A. Exploring the Mechanism of Grignard Metathesis Polymerization of 3-Alkylthiophenes. Dalt. Trans. 2014, 43 (40), 15143–15150 DOI: 10.1039/c4dt01617c.
Bilbrey, J. A.; Sontag, S. K.; Huddleston, N. E.; Allen, W. D.; Locklin, J. On the Role of Disproportionation Energy in Kumada Catalyst-Transfer Polycondensation. ACS Macro Lett. 2012, 1 (8), 995–1000 DOI: 10.1021/mz3002929.
Bilbrey, J. A.; Bootsma, A. N.; Bartlett, M. A.; Locklin, J.; Wheeler, S. E.; Allen, W. D. Ring-Walking of Zerovalent Nickel on Aryl Halides. J. Chem. Theory Comput. 2017, 13 (4), 1706–1711 DOI: 10.1021/acs.jctc.6b01143.
Sontag, S. K.; Bilbrey, J. A.; Huddleston, N. E.; Sheppard, G. R.; Allen, W. D.; Locklin, J. Π-Complexation in Nickel-Catalyzed Cross-Coupling Reactions. J. Org. Chem. 2014, 79 (4), 1836–1841 DOI: 10.1021/jo402259z.
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 (21), 8500–8508 DOI: 10.1021/ma401809e.
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 (20), 7638–7641 DOI: 10.1021/ma901888h.
Van den Bergh, K.; Huybrechts, J.; Verbiest, T.; Koeckelberghs, G. Transfer of Supramolecular Chirality in Block Copoly(Thiophene)S. Chemistry 2008, 14 (30), 9122–9125 DOI: 10.1002/chem.200801537.
Lin, H. C.; Shellaiah, M.; Ramakrishnam Raju, M. V.; Singh, A.; Lin, H. C.; Wei, K. H. Synthesis of Novel Platinum Complex Core as a Selective Ag+sensor and Its H-Bonded Tetrads Self-Assembled with Triarylamine Dendrimers for Electron/Energy Transfers. J. Mater. Chem. A 2014, 2 (41), 17463–17476 DOI: 10.1039/c4ta04231j.
Senkovskyy, V.; Khanduyeva, N.; Komber, H.; Oertel, U.; Stamm, M.; Kuckling, D.; Kiriy, A. Conductive Polymer Brushes of Regioregular Head-to-Tail Poly(3-Alkylthiophenes) via Catalyst-Transfer Surface-Initiated Polycondensation. J. Am. Chem. Soc. 2007, 129 (20), 6626–6632 DOI: 10.1021/ja0710306.