Efficient tin-free route to a donor-acceptor semiconducting copolymer with variable molecular weights / 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. // Macromolecules. - 2014. - V. 47, l. 12. - P. 3845-3851.

ISSN:

00249297

Type:

Article

Abstract:

For the fabrication of efficient photovoltaic devices and thin-film transistors, π-conjugated polymers with high molecular weight are desirable as they frequently show superior charge transport, morphological, and film-forming properties. Herein, we present an extremely fast tin-free method to polymerize a naphthalene diimide-dithiophene-based anion-radical monomer in the presence of Pd catalyst having bulky and electron-rich tritert-butylphosphine ligands (Pd/PtBu3). With this method, the corresponding semiconducting polymer, PNDIT2 (also known as P(NDI2OD-T2 or N2200) with a molecular weight in excess of 1000 kg/mol can be obtained quickly at room temperature and at rather low catalyst concentrations. In general, molecular weights of resulting polymer can be regulated by reaction conditions (e.g., catalyst concentration and reaction time). Besides high molecular weight PNDIT2 (e.g., with MN ∼ 350 kg/mol, M =2.9), PNDIT2 with moderate molecular weight (e.g., MN ∼ 110 kg/mol, M = 2.3) and low molecular weight (e.g., MW ∼ 12 kg/mol, M = 1.9), can also be obtained. It was found that thus-prepared PNDIT2 exhibits field-effect electron mobilities of up to ∼0.31 cm2/(V s), similar to the Stille-derived N2200 control polymer (up to ∼0.33 cm 2/(V s)). Preliminary studies demonstrated that Pd/P tBu3 catalyst is remarkably efficient in polymerizing of other anion-radical monomers, such as isoindigo-, and diketopyrrolopyrrole-based ones, although conventional Ni and Pd catalysts (e.g., Ni(dppp)Cl2, Ni(dppp)Cl2, Pd(PPh3)4) failed to polymerize these monomers. © 2014 American Chemical Society.

Author keywords:

Index keywords:

Catalyst supports; Monomers; Naphthalene; Nickel; Tin; Catalyst concentration; Film-forming properties; High molecular weight; Low molecular weight; Photovoltaic devices; Reaction conditions; Semicond

DOI:

10.1021/ma5007667

Смотреть в Scopus:

https://www.scopus.com/inward/record.uri?eid=2-s2.0-84903147650&doi=10.1021%2fma5007667&partnerID=40&md5=e81a4970e8ea78ca6ad5b0f606b911ca

Соавторы в МНС:

—

Другие поля

Поле	Значение
Link	https://www.scopus.com/inward/record.uri?eid=2-s2.0-84903147650&doi=10.1021%2fma5007667&partnerID=40&md5=e81a4970e8ea78ca6ad5b0f606b911ca
Affiliations	Leibniz-Institut für Polymerforschung Dresden E.V, Hohe Straße 6, 01069 Dresden, Germany; NOVALED GmbH, Tatzberg 49, 01307 Dresden, Germany; Center for Advancing Electronics Dresden (Cfaed), Technische Universität Dresden, 01062, Dresden, Germany; Ural Federal University, Mira str., 28, 620002, Yekaterinburg, Russian Federation; Center of Excellence for Advanced Materials Research (CEAMR), King Abdulaziz University, Jeddah, Saudi Arabia; Polyera Corporation, Skokie, IL 60077, United States
References	Sokolov, A.N., Tee, B.C.-K., Bettinger, C.J., Tok, J.B.-H., Bao, Z., (2012) Acc. Chem. Res., 45, p. 361; Arias, A.C., Mackenzie, J.D., McCulloch, I., Rivnay, J., Salleo, A., (2010) Chem. Rev., 110, p. 3; Beaujuge, P.M., Frechet, J.M.J., (2011) J. Am. Chem. Soc., 133, p. 20009; Facchetti, A., (2010) Chem. Mater., 23, p. 733; McCulloch, I., Ashraf, R.S., Biniek, L., Bronstein, H., Combe, C., Donaghey, J.E., James, D.I., Zhang, W., (2012) Acc. Chem. Res., 45, p. 714; Kola, S., Sinha, J., Katz, H.E., (2012) J. Polym. Sci. B Polym. Phys., 50, p. 1090; Li, H., Giri, G., Tok, J.B.-H., Bao, Z., (2013) MRS Bull., 38, p. 34; Osaka, I., Zhang, R., Sauvé, G., Smilgies, D.-M., Kowalewski, T., McCullough, R.D., (2009) J. Am. Chem. Soc., 131, p. 2521; Ahmed, E., Kim, F.S., Xin, H., Jenekhe, S.A., (2009) Macromolecules, 42, p. 8615; Baklar, M., Wobkenberg, P.H., Sparrowe, D., Goncalves, M., McCulloch, I., Heeney, M., Anthopoulos, T., Stingelin, N., (2010) J. Mater. Chem., 20, p. 1927; Osaka, I., Abe, T., Shinamura, S., Miyazaki, E., Takimiya, K., (2010) J. Am. Chem. Soc., 132, p. 5000; Baeg, K.-J., Khim, D., Jung, S.-W., Kang, M., You, I.-K., Kim, D.-Y., Facchetti, A., Noh, Y.-Y., (2012) Adv. Mater., 24, p. 5433; Matthews, J.R., Niu, W., Tandia, A., Wallace, A.L., Hu, J., Lee, W.-Y., Giri, G., He, M., (2013) Chem. Mater., 25, p. 782; Ortiz, R.P., Herrera, H., Seoane, C., Segura, J.L., Facchetti, A., Marks, T.J., (2012) Chem.-Eur. J., 18, p. 532; Alonzi, M., Lanari, D., Marrocchi, A., Petrucci, C., Vaccaro, L., (2013) RSC Adv., 3, p. 23909; Li, J., Zhao, Y., Tan, H.S., Guo, Y.L., Di, C.A., Yu, G., Liu, Y.Q., Ong, B.S., (2012) Sci. Rep., 2, p. 754; Tsao, H.N., Cho, D.M., Park, I., Hansen, M.R., Mavrinskiy, A., Yoon, D.Y., Graf, R., Müllen, K., (2011) J. Am. Chem. Soc., 133, p. 2605; Carsten, B., He, F., Son, H.J., Xu, T., Yu, L., (2011) Chem. Rev., 111, p. 1493; Marrocchi, A., (2012) Curr. Org. Synth., 9 (2), p. 149; Sakamoto, J., Rehahn, M., Wegner, G., Schlüter, A.D., (2009) Macromol. Rapid Commun., 30, p. 653; Osaka, I., McCullough, R.D., (2008) Acc. Chem. Res., 41, p. 1202; Yokozawa, T., Yokoyama, A., (2009) Chem. Rev., 109, p. 5595; Geng, Y.H., Huang, L.S., Wu, P., Wang, F.S., (2010) Sci. China Chem., 53, p. 1620; Okamoto, K., Luscombe, C.K., (2011) Polym. Chem., 2, p. 2424; Marshall, N., Sontag, S.K., Locklin, J., (2011) Chem. Commun., 47, p. 5681; Lanni, E.L., McNeil, A., (2009) J. Am. Chem. Soc., 131, p. 16573; Kiriy, A., Senkovskyy, V., Sommer, M., (2011) Macromol. Rapid Commun., 32, p. 1503; Tkachov, R., Senkovskyy, V., Komber, H., Kiriy, A., (2011) Macromolecules, 44, p. 2006; Senkovskyy, V., Tkachov, R., Komber, H., Sommer, M., Heuken, M., Voit, B., Huck, W.T.S., Kiriy, A., (2011) J. Am. Chem. Soc., 131, p. 19966; Senkovskyy, V., Tkachov, R., Komber, H., John, A., Sommer, J.-U., Kiriy, A., (2012) Macromolecules, 5, p. 7770; Liu, W., Tkachov, R., Komber, H., Senkovskyy, V., Schubert, M., Neher, D., Zhao, W., Kiriy, A., (2014) Polym. Chem., , 0.1039/C3PY01707A; Tkachov, R., Senkovskyy, V., Beryozkina, T., Boyko, K., Bakulev, V., Lederer, A., Sahre, K., Kiriy, A., (2014) Angew. Chem., Int. Ed., 53, p. 2402; Chen, Z., Zheng, Y., Yan, H., Facchetti, A., (2009) J. Am. Chem. Soc., 131, p. 8; Zhan, X., Tan, Z., An, B., Domercq, Z., Zhang, X., Barlow, S., Li, Y., Marder, S.R., (2007) J. Am. Chem. Soc., 129, p. 7246; Schubert, M., Dolfen, D., Frisch, J., Roland, S., Steyrleuthner, R., Stiller, B., Chen, Z., Neher, D., (2012) Adv. Energy Mater., 2, p. 369; Steyrleuthner, R., Schubert, M., Jaiser, F., Blakesley, J.C., Chen, Z., Facchetti, A., Neher, D., (2010) Adv. Mater., 22, p. 2799; Steyrleuthner, R., Schubert, M., Howard, I., Klaumunzer, B., Schilling, K., Chen, Z.H., Saalfrank, P., Facchetti Neher A, D., (2012) J. Am. Chem. Soc., 134, p. 18303; Moore, J.R., Albert-Seifried, S., Rao, A., Massip, S., Watts, B., Morgan, D.J., Friend, R.H., Sirringhaus, H., (2011) Adv. Energy Mater., 1 (2), pp. 230-240; Fabiano, S., Musumeci, C., Chen, Z., Scandurra, A., Wang, H., Loo, Y.-L., Facchetti, A., Pignataro, B., (2012) Adv. Mater., 24, p. 951; Rivnay, J., Steyrleuthner, R., Jimison, L.H., Casadei, A., Chen, Z., Toney, M.F., Facchetti, A., Salleo, A., (2011) Macromolecules, 44, p. 5246; Mori, D., Benten, H., Okada, I., Ohkita, H., Ito, S., (2014) Adv. Energy Mater., 2 (2), pp. 229-237; Yan, H., Chen, Z., Zheng, Y., Newman, C., Quinn, J.R., Dötz, F., Kastler, M., Facchetti, A., (2009) Nature, 457, p. 679; Dai, C., Fu, G.C., (2001) J. Am. Chem. Soc., 123, p. 2719; Fu, G.C., (2008) Acc. Chem. Res., 41, p. 1555; Biscoe, M.R., Barder, T.E., Buchwald, S.L., (2007) Angew. Chem., Int. Ed., 46, p. 7232; Yokoyama, A., Suzuki, H., Kubota, Y., Ohuchi, K., Higashimura, H., Yokozawa, T., (2007) J. Am. Chem. Soc., 129, p. 7236; Beryozkina, T., Boyko, K., Khanduyeva, N., Senkovskyy, V., Horecha, M., Oertel, U., Simon, F., Kiriy, A., (2009) Angew. Chem., Int. Ed., 48, p. 2695; Huddleston, N.E., Sontag, S.K., Bilbrey, J., Sheppard, G., Locklin, J., (2012) Macromol. Rapid Commun., 33, p. 2115; Kang, S., Ono, R.J., Bielawski, C.W., (2013) J. Am. Chem. Soc., 135, p. 4984; Elmalem, E., Kiriy, A., Huck, W.T.S., (2011) Macromolecules, 44, p. 9057; Elmalem, E., Biedermann, F., Johnson, K., Friend, R.H., Huck, W.T.S., (2012) J. Am. Chem. Soc., 134, p. 17769; Farina, V., (2004) Adv. Synth. Catal., 346, p. 1553; Steyrleuthner, R., Schubert, M., Howard, I., Klaumünzer, B., Schilling, K., Chen, Z., Saalfrank, P., Neher, D., (2012) J. Am. Chem. Soc., 134, p. 18303; Matthews, J.R., Niu, W., Tandia, A., Wallace, A.L., Hu, J., Lee, W.-Y., Giri, G., He, M., (2013) Chem. Mater., 25, p. 782; Kuwabara, J., Nohara, Y., Choi, S.J., Fujinami, Y., Lu, W., Yoshimura, K., Oguma, J., Kanbara, T., (2013) Polym. Chem., 4, p. 947. , Although previously reported polycondensations based on direct arylation reaction proceed at high reaction temperatures above 100°C and require reagents which are not present in the polymerization mixtures studied herein, this cross-linking pathway cannot be a priori excluded. See, for example; Kiriy, A., Stamm, M., (2012) Polymer Science: A Comprehensive Reference, 1, p. 367. , In; Matyjaszewski, K. Möller, M. Elsevier BV: Amsterdam, Vol; Kiriy, N., Jähne, E., Adler, H.-J., Schneider, M., Kiriy, A., Gorodyska, G., Minko, S., Stamm, M., (2003) Nano Lett., 3, p. 707; Kiriy, A., Gorodyska, A., Minko, S., Jaeger, W., Štěpánek, P., Stamm, M., (2002) J. Am. Chem. Soc., 124, p. 13454; Luzio, A., Fazzi, D., Natali, D., Giussani, E., Baeg, K.-J., Chen, Z., Noh, Y.-Y., Caironi, M., (2014) Adv. Funct. Mater., 24, p. 1151; Baeg, K.-J., Facchetti, A., Noh, Y.-Y., (2012) J. Mater. Chem., 22, p. 21138
Correspondence Address	Facchetti, A.; Center of Excellence for Advanced Materials Research (CEAMR), King Abdulaziz University, Jeddah, Saudi Arabia; email: a-facchetti@northwestern.edu
Publisher	American Chemical Society
CODEN	MAMOB
Language of Original Document	English
Abbreviated Source Title	Macromolecules
Source	Scopus