Diaminocarbene Palladium(II) Catalyzed Suzuki Polycondensation as a Simple and Efficient Way for Synthesis of <italic style="font-style: italic">π</italic>-Conjugated Polymers

Anton A. Yakimanskiy; Elena V. Zhukova; Anna V. Kashina; Elena L. Krasnopeeva; Ilya E. Kolesnikov; Artem V. Dmitriev; Sergey I. Pozin; Natalia V. Nekrasova; Alexei E. Alexandrov; Dmitry A. Lypenko; Tatiana G. Chulkova; Alexander V. Yakimansky

doi:10.1007/s10118-025-3448-x

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Diaminocarbene Palladium(II) Catalyzed Suzuki Polycondensation as a Simple and Efficient Way for Synthesis of π-Conjugated Polymers

RESEARCH ARTICLE | Updated：2025-12-03

- Diaminocarbene Palladium(II) Catalyzed Suzuki Polycondensation as a Simple and Efficient Way for Synthesis of π-Conjugated Polymers
- Diaminocarbene Palladium(II) Catalyzed Suzuki Polycondensation as a Simple and Efficient Way for Synthesis of π-Conjugated Polymers
- Chinese Journal of Polymer Science 2025年43卷第12期页码：2222-2230
- Affiliations：
  
  a.Branch of Petersburg Nuclear Physics Institute Named by B.P. Konstantinov of National Research Centre "Kurchatov Institute" – Institute of Macromolecular Compounds, 31 Bolshoy pr. V.O., Saint Petersburg 199004, Russia
  b.Saint Petersburg State University, 7/9 Universitetskaya nab., Saint Petersburg 199034, Russia
  c.Frumkin Institute of Physical Chemistry and Electrochemistry of the Russian Academy of Sciences, 31/bld.4 Leninskiy Prospect, Moscow 119071, Russia
- Author bio：
  
  yakimansky@yahoo.com
- Funds：
  
  This work was financially supported by the Russian Science Foundation (No. 23-43-00060). The authors acknowledge the Center for Optical and Laser Materials Research (SPbSU) and Saint Petersburg State University for measuring the quantum yields of luminescence within the framework of Research Project No. АААА-А19-119082790069-6.;Electronic supplementary information (ESI) is available free of charge in the online version of this article at http://doi.org/10.1007/s10118-025-3448-x.
- DOI：10.1007/s10118-025-3448-x
  中图分类号：
- 收稿：2025-07-15，
  
  录用：2025-09-03，
  
  网络出版：2025-11-19，
  
  纸质出版：2025-12-15
- Accepted：
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Yakimanskiy, A. A.; Zhukova, E. V.; Kashina, A. V.; Krasnopeeva, E. L.; Kolesnikov, I. E.; Dmitriev, A. V.; Pozin, S. I.; Nekrasova, N. V.; Alexandrov, A. E.; Lypenko, D. A.; Chulkova, T. G.; Yakimansky, A. V. Diaminocarbene palladium(II) catalyzed Suzuki polycondensation as a simple and efficient way for synthesis of π-conjugated polymers. Chinese J. Polym. Sci. 2025, 43, 2222–2230

Anton A. Yakimanskiy, Elena V. Zhukova, Anna V. Kashina, et al. Diaminocarbene Palladium(II) Catalyzed Suzuki Polycondensation as a Simple and Efficient Way for Synthesis of π-Conjugated Polymers[J]. Chinese Journal of Polymer Science, 2025, 43(12): 2222-2230.
Yakimanskiy, A. A.; Zhukova, E. V.; Kashina, A. V.; Krasnopeeva, E. L.; Kolesnikov, I. E.; Dmitriev, A. V.; Pozin, S. I.; Nekrasova, N. V.; Alexandrov, A. E.; Lypenko, D. A.; Chulkova, T. G.; Yakimansky, A. V. Diaminocarbene palladium(II) catalyzed Suzuki polycondensation as a simple and efficient way for synthesis of π-conjugated polymers. Chinese J. Polym. Sci. 2025, 43, 2222–2230 DOI： 10.1007/s10118-025-3448-x.

Anton A. Yakimanskiy, Elena V. Zhukova, Anna V. Kashina, et al. Diaminocarbene Palladium(II) Catalyzed Suzuki Polycondensation as a Simple and Efficient Way for Synthesis of π-Conjugated Polymers[J]. Chinese Journal of Polymer Science, 2025, 43(12): 2222-2230. DOI： 10.1007/s10118-025-3448-x.

摘要

Simple and efficient method of Suzuki polycondensation catalyzed by oxygen-stable Diaminocarbene Palladium(II) complexes is proposed. Compared to the conventional Suzuki polycondensation catalyzed by Pd(0) phosphine complexes

much lower catalyst loading is required to prepare polymers with high molecular weights and improved photophysical characteristics.

Abstract

An efficient

simple

and convenient method for Suzuki polycondensation using a diaminocarbene palladium(II) catalyst under aerobic conditions was developed. Reactions between aromatic diboronic acid bis(pinacol) ester and different aromatic dibromides

both with electron-donating and electron-withdrawing fragments in the structure

were carried out. Various reaction conditions

such as the effect of catalyst concentration and solvent

were investigated. The molecular weight characteristics

photo- and electroluminescence properties of the synthesized polymers were studied.

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references

Rehahn, M.; Schlüter, A. D.; Wegner, G.; Feast, W. J. Soluble poly(para-phenylene)s. 2. Improved synthesis of poly(para-2,5-di-n-hexylphenylene) via Pd-catalysed coupling of 4-bromo-2,5-di-n-hexylbenzeneboronic acid. Polymer (Guildf). 1989 , 30 , 1060−1062..

Rehahn, M.; Schlüter, A.; Wegner, G. Variation of the length and the density of the solubilizing side chains. Makromol. Chem. 1990 , 191 , 1991−2003..

Rehahn, M.; Schlüter, A.; Wegner, G. Pd-catalyzed polycondensation of aromatic monomers with functional groups. Die Makromol. Chemie, Rapid Commun. 1990 , 11 , 535−539..

Schlüter, A. D. The tenth anniversary of Suzuki polycondensation (SPC). J. Polym. Sci. Part A Polym. Chem. 2001 , 39 , 1533−1556..

Sakamoto, J.; Rehahn, M.; Wegner, G.; Schlüter, A. D. Suzuki polycondensation: polyarylenes à la carte. Macromol. Rapid Commun. 2009 , 30 , 653−687..

Littke, A. F.; Dai, C.; Fu, G. C. Versatile catalysts for the Suzuki cross-coupling of arylboronic acids with aryl and vinyl halides and triflates under mild conditions. J. Am. Chem. Soc. 2000 , 122 , 4020−4028..

Kinzel, T.; Zhang, Y.; Buchwald, S. L. A new palladium precatalyst allows for the fast Suzuki-Miyaura coupling reactions of unstable polyfluorophenyl and 2-heteroaryl boronic acids. J. Am. Chem. Soc. 2010 , 132 , 14073−14075..

Molander, G. A.; Trice, S. L. J.; Kennedy, S. M. Scope of the two-step, one-pot palladium-catalyzed bor ylation/Suzuki cross-coupling reaction utilizing bis-boronic acid. J. Org. Chem. 2012 , 77 , 8678−8688..

Miyaura, N.; Suzuki, A. Palladium-catalyzed cross-coupling reactions of organoboron compounds. Chem. Rev. 1995 , 95 , 2457−2483..

Lin, J. Y.; Liu, B.; Yu, M. N.; Wang, X. H.; Bai, L. B.; Han, Y. M.; Ou, C. J.; Xie, L. H.; Liu, F.; Zhu, W. S.; Zhang, X. W.; Ling, H. F.; Stavrinou, P. N.; Wang, J. P.; Bradley, D. D. C.; Huang, W. Systematic investigation of self-organization behavior in supramolecular π -conjugated polymer for multi-color electroluminescence. J. Mater. Chem. C 2018 , 6 , 1535−1542..

Sanzone, A.; Calascibetta, A.; Monti, M.; Mattiello, S.; Sassi, M.; Corsini, F.; Griffini, G.; Sommer, M.; Beverina, L. Synthesis of conjugated polymers by sustainable Suzuki polycondensation in water and under aerobic conditions. ACS Macro Lett. 2020 , 9 , 1167−1171..

Subbiah, J.; Mitchell, V. D.; Hui, N. K. C.; Jones, D. J.; Wong, W. W. H. A green route to conjugated polyelectrolyte interlayers for high-performance solar cells. Angew. Chem. Int. Ed. 2017 , 56 , 8431−8434..

Grätz, S.; Wolfrum, B.; Borchardt, L. MechanochemicalSuzuki polycondensation-from linear to hyperbranched polyphenylenes. Green Chem. 2017 , 19 , 2973−2979..

Luzyanin, K. V.; Tskhovrebov, A. G.; Carolina Carias, M.; Fátima C Guedes Da Silva, M.; Pombeiro, A. J. L.; Kukushkin, V. Y. Novel metal-mediated (M = Pd, Pt) coupling between isonitriles and benzophenone hydrazone as a route to aminocarbene complexes exhibiting high catalytic activity (M = Pd) in the Suzuki-Miyaura reaction. Organometallics 2009 , 28 , 6559−6566..

Valishina, E. A.; Buslaeva, T. M.; Luzyanin, K. V. New acyclic aminocarbene palladium(II) complexes as convenient catalysts for the Sonogashira and Suzuki cross-coupling. Russ. Chem. Bull. 2013 , 62 , 1361−1365..

Chulkova, T. G.; Krutin, D. V.; Simdianov, I. V.; Saprykina, N. N.; Yakimansky, A. V. Effect of the structure of C,N-chelate diaminocarbene palladium(II) complexes on their catalytic activity in the suzuki reaction. Russ. J. Appl. Chem. 2023 , 96 , 818−824..

Lypenko, D. A.; Aleksandrov, A. E.; Dmitriev, A. V.; Yakimanskiy, A. A.; Kolesnikov, I. E.; Chulko va, T. G.; Yakimansky, A. V.; Tameev, A. R. Photocurrent in the polyfluorene copolymer/PTCDI heterojunction enhanced by reabsorption of fluorescence emission. Chinese J. Polym. Sci. 2024 , 42 , 1941−1947..

Nosova, G. I.; Lypenko, D. A.; Smyslov, R. Y.; Berezin, I. A.; Zhukova, E. V.; Mal’Tsev, E. I.; Dmitriev, A. V.; Litvinova, L. S.; Solovskaya, N. A.; Dobrokhotov, O. V.; Abramov, I. G.; Yakimanskii, A. V. Synthesis and photo- and electroluminescent properties of copolyfluorenes with nile red fragments in side chains. Polym. Sci. - Ser. B 2014 , 56 , 59−76..

Demina, N. S.; Rasputin, N. A.; Irgashev, R. A.; Tameev, A. R.; Nekrasova, N. V.; Rusinov, G. L.; Nunzi, J. M.; Charushin, V. N. Benzo[b ] selenophene/thieno[3,2-b ] indole-based N,S,Se-heteroacenes for hole-transporting layers. ACS Omega 2020 , 5 , 9377−9383..

Namazian, M.; Lin, C. Y.; Coote, M. L. Benchmark calculations of absolute reduction potential of ferricinium/ferrocene couple in nonaqueous solutions. J. Chem. Theory Comput. 2010 , 6 , 2721−2725..

Yakimanskiy, A. A.; Kaskevich, K. I.; Zhukova, E. V.; Berezin, I. A.; Litvinova, L. S.; Chulkova, T. G.; Lypenko, D. A.; Dmitriev, A. V.; Pozin, S. I.; Nekrasova, N. V.; Tomilin, F. N.; Ivanova, D. A.; Yakimansky, A. V. Synthesis, photo- and electroluminescence of new polyfluorene copolymers containing dicyanostilbene and 9,10-dicyanophenanthrene in the main chain. Materials 2023 , 16 , 5592..

Malov, V. V.; Ghosh, T.; Nair, V. C.; Maslov, M. M.; Katin, K. P.; Unni, K. N. N.; Tameev, A. R. Hole mobility in thieno[3,2-b ] thiophene oligomers. Mendeleev Commun. 2019 , 29 , 218−219..

Nosova, G. I.; Lypenko, D. A.; Smyslov, R. Y.; Zhukova, E. V.; Berezin, I. A.; Litvinova, L. S.; Maltsev, E. I.; Yakimansky, A. V. Copolyfluorenes containing carbazole or triphenylamine and diethoxylphosphoryl groups in the side chains as white-light-emitting polymers. Polymer 2020 , 210 , 122978..

Bai, K.; Wang, S.; Zhao, L.; Ding, J.; Wang, L. Efficient blue, green, and red electroluminescence from carbazole-functionalized poly(spirobifluorene)s. Macromolecules 2017 , 50 , 6945−6953..

Liu, B.; Yu, W. L.; Lai, Y. H.; Huang, W. Blue-light-emitting fluorene-based polymers with tunable electronic properties. Chem. Mater. 2001 , 13 , 1984−1991..

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Diaminocarbene Palladium(II) Catalyzed Suzuki Polycondensation as a Simple and Efficient Way for Synthesis of π-Conjugated Polymers

Diaminocarbene Palladium(II) Catalyzed Suzuki Polycondensation as a Simple and Efficient Way for Synthesis of π-Conjugated Polymers

DOI：10.1007/s10118-025-3448-x

摘要

Abstract

关键词

Keywords

references