Chemistry - A European Journal
10.1002/chem.201800642
COMMUNICATION
Keywords: dehydration, conjugated polymer, conjugated
[
[
[
32]
A
similar polymer has recently been prepared via palladium
catalysis: Q. Guo, R. Jiang, D. Wu, J. You, Macromol. Rapid
Commun. 2016, 37, 794−798.
material, organic materials, organic methods
33] Appearance of polymer is visually apparent immediately following
base addition. See supporting video and supporting information for
details.
[
[
[
[
[
1] Y.-J. Cheng, S.-H. Yang, C.-S. Hsu, Chem. Rev. 2009, 109, 5868-
923.
2] C. Liu, K. Wang, X. Gong, A. J. Hegger, Chem. Soc. Rev. 2016, 45,
825-4846.
5
34] While the structure is drawn in a regioregular fashion for simplicity,
the true structure of the polymers is most likely regiorandom.
4
3] A.C Grimsdale, L.K. Chan, R.E. Martin, P.G. Jokisz, A.B. Holmes,
Chem. Rev. 2009, 109, 897-1091.
4] I.F. Perepichka, D.F. Perepichka, H. Meng, F. Wudl, Adv. Mater.
2
005, 17, 2281-2305.
5] S.W. Thomas, G.D. Joly, T.M. Swager, Chem. Rev. 2007, 107,
339−1386.
1
[
[
6] A. Facchetti, Chem. Mater. 2011, 23, 733-758.
7] L. Dou, Y. Liu, Z. Hong, G. Li, Y. Yang, Chem. Rev. 2015, 115,
1
2633-12665.
8] P.M. Beaujuge, J.M.J. Frechet, J. Am. Chem. Soc. 2011, 133,
0009-20029.
9] S. Xu, E.H. Kim, A. Wei, E.-j. Negishi, Sci. Technol. Adv. Mater.
014, 15, 44201.
10] B. Carsten, F. He, H.J. Son, T. Xu, L. Yu, Chem. Rev. 2011, 111,
493−1528.
[
[
[
[
[
2
2
1
11] J. Sakamoto, M. Rehahn, G. Wegner, A.D. Schlüter, Macromol.
Rapid Commun. 2009, 30, 653−687.
12] Y. Geng, L. Huang, S. Wu, F. Wang, Sci. China: Chem. 2010, 53,
1
620−1633.
[
[
13] S. Huo, R. Mroz, J. Carroll, Org. Chem. Front. 2015, 2, 416−445.
14] K. Okamoto, J. Zhang, J.B. Housekeeper, S.R. Marder, C.K.
Luscombe, Macromolecules 2013, 46, 8059- 8078.
[
[
[
15] J.-R. Pouliot, F. Grenier, J.T. Blaskovits, S. Beaupre, M. Leclerc,
Chem. Rev. 2016, 116, 14225-14274.
16] M.P. Nikiforov, B. Lai, W. Chen, S. Chen, R.D. Schaller, J. Strzalka,
J. Maser, S.B. Darling, Energ. Environ, Sci, 2013, 6, 1513-1520.
17] N. Camaioni, F. Tinti, L. Franco, M. Fabris, A. Toffoletti, M. Ruzzi,
L. Montanari, L. Bonoldi, A. Pellegrino, A. Calabrese, R. Po, Org.
Elec. 2012, 13, 550-559.
[
[
[
18] S.-Y, Liu, H.-Y. Li, M.-M. Shi, H. Jiang, X.-L. Hu, W.-Q. Li, L. Fu,
H.-Z. Chen, Macromolecules. 2012, 45, 9004-9009.
19] D. Klemm, B. Heublein, H.-P. Fink, A. Bohn, Angew. Chem. Int. Ed.
2
005, 44, 3358-3393.
20] American Chemical Society National Historic Chemical Landmarks.
Bakelite: The World’s First Synthetic Plastic.
marks/bakelite.html (accessed October 20, 2017).
[
[
21] E.T Strom, S.C. Rasmussen, “100+ Years of Plastics: Leo
Baekeland and Beyond.” ACS Symp. Ser., 1080 (2011).
22] D. Dave, “IHS Chemical PEP Review 2015-06 Polyamide 6 and 66
Process Summary” (2015) https://www.ihs.com/products/report-
pepreview-2015-06-polyamide-nylon-6-and-66.html
October 20, 2017).
(accessed
[
23] Merchant
Research
&
Consulting
(2014)
439-mln-tonnes-2015.html (accessed October 20, 2017).
2
[
[
[
[
[
24] H.L. Su, D.N. Sredojevic, H. Bronstein, T.J. Marks, B.C. Schroeder,
M. Al-Hashimi, Macromol. Rapid Commun. 2017, 38, 1600610.
25] D. Bevk, L. Marin, L. Lutsen, D. Vanderzande, W. Maes, RSC Adv.
2
013, 3, 11418-11431.
26] G. Reginato, A. Mordini, L. Zani, M. Calamante, A. Dessi, Eur. J.
Org. Chem. 2016, 2016, 233-251.
27] L.-C. Campeau, M. Bertrand-Laperle, J.P. Leclerc, E. Villemure, S.
Gorelsky, K. Fagnou, J. Am. Chem. Soc. 2008, 130, 3276-3277.
28] L.-C. Campeau, D.R. Stuart, J.-P. Leclerc, M. Bertrand-Laperle, E.
Villemure, H.-Y. Sun, S. Lasserre, N. Guimond, M. Lecavallier, K.
Fagnou. J. Am. Chem. Soc. 2009 131, 3291-3306.
[
29] The overall yield for all possible dehydration products was 88% for
1
5 and 89% for 16 with the mass balance represented in homo-
dehydration adducts.
[
[
30] See supporting information for details.
31] J.M.G. Cowie, V. Arrighi, “Polymers: chemistry
&
physics of
modern materials.” Chapman & Hall, New York, 436 (1991)
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