Angewandte Chemie International Edition
10.1002/anie.201903765
Chem. Int. Ed. 2015, 54, 10322. G. Yin, I. Kalvet, F. Schoenebeck,
Angew. Chem. Int. Ed. 2015, 54, 6809
14] S. T. Keaveney, G. Kundu, F. Schoenebeck, Angew. Chem. Int. Ed.
(
GPC) analyses of the synthesized polymers as well as helpful
discussions.
[
2
018, 57, 12573-12577.
Additional Notes
[15] a) M. J. Baek, W. Jang, S. H. Lee, Y. S. Lee, Synth. Met. 2012, 161,
2
7
785-2791; b) M. Imit, P. Imin, A. Adronov, Can. J. Chem. 2016, 94,
59-768; c) M. Boota, M. Pasini, F. Galeotti, W. Porzio, M. Q. Zhao, J.
A patent application has been filed by RWTH Aachen University on
this research.
Halim, Y. Gogotsi, Chem. Mater. 2017, 29, 2731-2738; d) Y. Wang, T.
Harada, L. Q. Phuong, Y. Kanemitsu, T. Nakano, Macromolecules
2
018, 51, 6865-6877; e) C. D. Muller, A. Falcou, N. Reckefuss, M.
Received: ((will be filled in by the editorial staff))
Published online on ((will be filled in by the editorial staff))
Rojahn, V. Wiederhirn, P. Rudati, H. Frohne, O. Nuyken, H. Becker,
K. Meerholz, Nature 2003, 421, 829-833.
[
[
16] R. Tkachov, V. Senkovskyy, T. Beryozkina, K. Boyko, V. Bakulev, A.
Lederer, K. Sahre, B. Voit, A. Kiriy, Angew. Chem. Int. Ed. 2014, 53,
Keywords: Pd(I) dimer • cross-coupling • polymerization • selectivity
2
402-2407.
17] If ligand:metal ratio is not 1:1, then vastly decreased reactivity or even
different selectivity results, see: a) C. C. C. Johansson Seechurn, M. O.
Kitching, T. J. Colacot, V. Snieckus, Angew. Chem. Int. Ed. 2012, 51,
5062-5085; b) U. Christmann, R. Vilar, Angew. Chem. Int. Ed. 2005,
44, 366-374; c) A. F. Littke, C. Dai, G. C. Fu, J. Am. Chem. Soc. 2000,
122, 4020-4028; d) F. Proutiere, F. Schoenebeck, Angew. Chem. Int.
Ed. 2011, 50, 8192-8195; e) F. Proutiere, E. Lyngvi, M. Aufiero, I. A.
Sanhueza, F. Schoenebeck, Organometallics 2014, 33, 6879-6884.
[
1] For an overview on opportunities and challenges with conductive
polymers, see: T. Nezakati, A. Seifalian, A. Tan, A. M. Seifalian, Chem.
Rev. 2018, 118, 6766−6843
[
[
[
2] For an review, see: Z. J. Bryan, A. J. McNeil, Macromolecules 2013,
4
6, 8395
3] A. K. Leone, E. A. Mueller, A. J. McNeil, J. Am. Chem. Soc. 2018, 140,
5126-15139.
1
[18] a) Note of safety: organometallic reagents may react violently with air
due to moisture sensitivity. All necessary safety precautions should
therefore be considered prior to operating under open-flask reaction
conditions. b) See supporting information for the reaction set-up. The
organozinc was prepared under inert conditions and added to a flask
containing the Pd dimer in solvent open to the laboratory atmosphere.
[19] J. P. Lutz, M. D. Hannigan, A. J. McNeil, Coord. Chem. Rev. 2018,
376, 225-247.
4] (a) Handbook of Conducting Polymers, 2nd ed.; Skotheim, T. A.;
Elsenbaumer, R. L., Reynolds, J. R.; Eds.; Marcel Dekker: New York,
1
998. (b) Advances in Synthetic Metals: Twenty Years of Progress in
Science and Technology; Bernier, P., Lefrant, S., Bidan, G., Eds.;
Elsevier: Lausanne, Switzerland, 1999;
(I)
[
[
5] A. Facchetti, Chem. Mater. 2011, 23, 733-758.
6] B. Liu, S. H. Ye, Y. P. Zou, B. Peng, Y. H. He, K. C. Zhou, Macromol.
Chem. Phys. 2011, 212, 1489-1496.
[20] A. Yokoyama, H. Suzuki, Y. Kubota, K. Ohuchi, H. Higashimura, T.
Yokozawa, J. Am. Chem. Soc. 2007, 129, 7236-7237.
[
[
7] a) C. Yuan, Q. Fang, RSC Advances 2012, 2; b) E. L. Lanni, A. J.
McNeil, J. Am. Chem. Soc. 2009, 131, 16573-16579.
8] a) A. G. Sui, X. C. Shi, Y. X. Wang, Y. H. Geng, F. S. Wang, Polymer
Chemistry 2015, 6, 4819-4827; b) T. Yokozawa, Y. Ohta, Chem. Rev.
[21] a) H. H. Zhang, W. Peng, J. Dong, Q. S. Hu, Acs Macro Letters 2016,
5, 656-660; b) H. H. Zhang, Q. S. Hu, K. Hong, Chem. Commun. 2015,
51, 14869-14872; c) H. H. Zhang, C. H. Xing, Q. S. Hu, K. L. Hong,
Macromolecules 2015, 48, 967-978; d) H. H. Zhang, C. H. Xing, Q. S.
Hu, J. Am. Chem. Soc. 2012, 134, 13156-13159; e) R. Grisorio, P.
Mastrorilli, G. P. Suranna, Polymer Chemistry 2014, 5, 4304-4310.
[22] M. Verswyvel, C. Hoebers, J. De Winter, P. Gerbaux, G.
Koeckelberghs, J. Polym. Sci. Pol. Chem. 2013, 51, 5067-5074.
[23] Upon further decrease in catalyst loading to ppm levels (0.0005 mol%)
no polymerization occurred, showing that trace levels of Palladium
cannot efficiently catalyse the polymerization reaction.
[24] a) H. P. Fang, J. W. Lin, I. H. Chiang, C. W. Chu, K. H. Wei, H. C. Lin,
J. Polym. Sci. Pol. Chem. 2012, 50, 5011-5022; b) A. G. Davies,
Organotin Chemistry, 2nd, Completely Revised and Updated Edition,
Wiley-VCH, 2004.
[25] H. Wen, Z. Ge, Y. Liu, T. Yokozawa, L. Lu, X. Ouyang, Z. Tan, Eur.
Polym. J. 2013, 49, 3740-3743.
[26] S. S. Zalesskiy, V. P. Ananikov, Organometallics 2012, 31, 2302-2309.
[27] For previous polymerization protocols to make polythiophene, see : J.
H. Bannock, N. D. Treat, M. Chabinyc, N. Stingelin, M. Heeney, J. C.
de Mello, Scientific Reports 2016, 6, 23651
[28] a) T. Yokozawa, H. Kohno, Y. Ohta, A. Yokoyama, Macromolecules
2010, 43, 7095-7100; b) R. Grisorio, G. Allegretta, P. Mastrorilli, G. P.
Suranna, Macromolecules 2011, 44, 7977-7986.
2
016, 116, 1950-1968; c) K. Müllen, J. R. Reynolds, T. Masuda,
Conjugated Polymers: A Practical Guide to Synthesis, 2013.
9] For a general overview of combinatorial polymer research, see: Michael
A. R. Meier and Ulrich S. Schubert, J. Mater. Chem. 2004, 14 , 3289
10] For reviews, see: a) D. A. Horton, G. T. Bourne, M. L. Smythe, Chem.
Rev. 2003, 103, 893; b) J. Hassan, M. Sévignon, C. Gozzi, E. Schulz,
M. Lemaire, Chem. Rev. 2002, 102, 1359; c) Transition Metal-
Catalyzed Couplings in Process Chemistry: Case Studies From the
Pharmaceutical Industry (Eds.: J. Magano, J. R. Dunetz), Wiley,
Hoboken, 2013; d) New Trends in Cross Coupling: Theory and
Applications (Ed.: T. Colacot), RSC Catalysis Series, Cambridge, UK,
[
[
2
015.
[
11] For reviews, see: a) J. Almond-Thynne, D. C. Blakemore, D. C. Pryde,
A. C. Spivey, Chem. Sci. 2017, 8, 40 – 62; b) R. Rossi, F. Bellina, M.
Lessi, Adv. Synth. Catal. 2012, 354, 1181; c) I. Fairlamb, Chem. Soc.
Rev. 2007, 36, 1036; d) S. Schrçter, C. Stock, T. Bach, Tetrahedron
2
005, 61, 2245.
12] a) I. Kalvet, G. Magnin, F. Schoenebeck, Angew. Chem. Int. Ed. 2017,
6, 1581-1585; b) I. Kalvet, T. Sperger, T. Scattolin, G. Magnin, F.
Schoenebeck, Angew. Chem. Int. Ed. 2017, 56, 7078-7082.
13] For other applications that demonstrate the air-stability and priviliged
catalysis reactivity, see: T. Sperger, F. Schoenebeck, Synthesis 2018,
[
[
5
5
1
0, 4471. T. Sperger, C. K. Stirner, F. Schoenebeck, Synthesis 2017, 49,
15. M. Aufiero, T. Sperger, A. S.-K. Tsang, F. Schoenebeck, Angew.
4
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