Three-Component Multiblock 1D Supramolecular Copolymers of Ir(III) Complexes with Controllable Sequences
Yan Chen
State Key Laboratory of Fine Chemicals, Frontier Science Center for Smart Materials, School of Chemical Engineering, Dalian University of Technology, Linggong Road 2, Dalian, 116024 China
Contribution: Investigation (lead), Methodology (lead), Writing - original draft (lead), Writing - review & editing (lead)
Search for more papers by this authorDr. Qingyun Wan
Department of Chemistry and State Key Laboratory of Synthetic Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, China
Contribution: Formal analysis (equal), Validation (equal)
Search for more papers by this authorDr. Yusheng Shi
State Key Laboratory of Fine Chemicals, Frontier Science Center for Smart Materials, School of Chemical Engineering, Dalian University of Technology, Linggong Road 2, Dalian, 116024 China
Contribution: Resources (supporting)
Search for more papers by this authorProf. Bingtao Tang
State Key Laboratory of Fine Chemicals, Frontier Science Center for Smart Materials, School of Chemical Engineering, Dalian University of Technology, Linggong Road 2, Dalian, 116024 China
Contribution: Resources (equal), Writing - review & editing (supporting)
Search for more papers by this authorCorresponding Author
Prof. Chi-Ming Che
Department of Chemistry and State Key Laboratory of Synthetic Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, China
Contribution: Resources (equal), Supervision (equal), Writing - review & editing (equal)
Search for more papers by this authorCorresponding Author
Prof. Chun Liu
State Key Laboratory of Fine Chemicals, Frontier Science Center for Smart Materials, School of Chemical Engineering, Dalian University of Technology, Linggong Road 2, Dalian, 116024 China
Contribution: Funding acquisition (lead), Project administration (lead), Supervision (lead), Writing - review & editing (lead)
Search for more papers by this authorYan Chen
State Key Laboratory of Fine Chemicals, Frontier Science Center for Smart Materials, School of Chemical Engineering, Dalian University of Technology, Linggong Road 2, Dalian, 116024 China
Contribution: Investigation (lead), Methodology (lead), Writing - original draft (lead), Writing - review & editing (lead)
Search for more papers by this authorDr. Qingyun Wan
Department of Chemistry and State Key Laboratory of Synthetic Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, China
Contribution: Formal analysis (equal), Validation (equal)
Search for more papers by this authorDr. Yusheng Shi
State Key Laboratory of Fine Chemicals, Frontier Science Center for Smart Materials, School of Chemical Engineering, Dalian University of Technology, Linggong Road 2, Dalian, 116024 China
Contribution: Resources (supporting)
Search for more papers by this authorProf. Bingtao Tang
State Key Laboratory of Fine Chemicals, Frontier Science Center for Smart Materials, School of Chemical Engineering, Dalian University of Technology, Linggong Road 2, Dalian, 116024 China
Contribution: Resources (equal), Writing - review & editing (supporting)
Search for more papers by this authorCorresponding Author
Prof. Chi-Ming Che
Department of Chemistry and State Key Laboratory of Synthetic Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, China
Contribution: Resources (equal), Supervision (equal), Writing - review & editing (equal)
Search for more papers by this authorCorresponding Author
Prof. Chun Liu
State Key Laboratory of Fine Chemicals, Frontier Science Center for Smart Materials, School of Chemical Engineering, Dalian University of Technology, Linggong Road 2, Dalian, 116024 China
Contribution: Funding acquisition (lead), Project administration (lead), Supervision (lead), Writing - review & editing (lead)
Search for more papers by this authorGraphical Abstract
Three-component multiblock 1D supramolecular copolymers with up to 9 blocks have been successfully synthesized by precise control of the pathway complexity of Ir(III) complexes. The segmented structures of the multiblock copolymers could be characterized by both TEM and SEM. These three-component block copolymers with tunable block sequences will advance the development of functional block copolymers.
Abstract
Multicomponent supramolecular block copolymers (BCPs) have attracted much attention due to their potential functionalities, but examples of three-component supramolecular BCPs are rare. Herein, we report the synthesis of three-component multiblock 1D supramolecular copolymers of Ir(III) complexes 1–3 by a sequential seeded supramolecular polymerization approach. Precise control over the kinetically trapped species via the pathway complexity of the monomers is the key to the successful synthesis of BCPs with up to 9 blocks. Furthermore, 5-block BCPs with different sequences could be synthesized by changing the addition order of the kinetic species during a sequentially seeded process. The corresponding heterogeneous nucleation-elongation process has been confirmed by the UV/Vis absorption spectra, and each segment of the multiblock copolymers could be characterized by both TEM and SEM. Interestingly, the energy transfer leads to weakened emission of 1-terminated and enhanced emission of 3-terminated BCPs. This study will be an important step in advancing the synthesis and properties of three-component BCPs.
Conflict of interest
The authors declare no conflict of interest.
Open Research
Data Availability Statement
The data that support the findings of this study are available in the supplementary material of this article.
Supporting Information
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References
- 1
- 1aT. Aida, E. W. Meijer, S. I. Stupp, Science 2012, 335, 813;
- 1bB. Adelizzi, N. J. Van Zee, L. N. J. de Windt, A. R. A. Palmans, E. W. Meijer, J. Am. Chem. Soc. 2019, 141, 6110;
- 1cE. P. Bruckner, S. I. Stupp, Polym. Int. 2022, 71, 590.
- 2
- 2aT. F. de Greef, E. W. Meijer, Nature 2008, 453, 171;
- 2bW. Zhang, W. Jin, T. Fukushima, A. Saeki, S. Seki, T. Aida, Science 2011, 334, 340;
- 2cA. Das, G. Vantomme, A. J. Markvoort, H. M. M. Ten Eikelder, M. Garcia-Iglesias, A. R. A. Palmans, E. W. Meijer, J. Am. Chem. Soc. 2017, 139, 7036;
- 2dB. Adelizzi, A. Aloi, A. J. Markvoort, H. M. M. Ten Eikelder, I. K. Voets, A. R. A. Palmans, E. W. Meijer, J. Am. Chem. Soc. 2018, 140, 7168.
- 3
- 3aM. Wehner, F. Würthner, Nat. Chem. Rev. 2020, 4, 38;
- 3bG. Ghosh, P. Dey, S. Ghosh, Chem. Commun. 2020, 56, 6757.
- 4
- 4aD. van der Zwaag, T. F. de Greef, E. W. Meijer, Angew. Chem. Int. Ed. 2015, 54, 8334;
- 4bJ. Matern, Y. Dorca, L. Sánchez, G. Fernández, Angew. Chem. Int. Ed. 2019, 58, 16730;
- 4cK. Sugiyasu, Polym. J. 2021, 53, 865;
- 4dH. Su, S. A. H. Jansen, T. Schnitzer, E. Weyandt, A. T. Rosch, J. Liu, G. Vantomme, E. W. Meijer, J. Am. Chem. Soc. 2021, 143, 17128.
- 5
- 5aS. Ogi, K. Sugiyasu, S. Manna, S. Samitsu, M. Takeuchi, Nat. Chem. 2014, 6, 188;
- 5bJ. Kang, D. Miyajima, T. Mori, Y. Inoue, Y. Itoh, T. Aida, Science 2015, 347, 646;
- 5cR. D. Mukhopadhyay, A. Ajayaghosh, Science 2015, 349, 241;
- 5dS. Ogi, V. Stepanenko, K. Sugiyasu, M. Takeuchi, F. Würthner, J. Am. Chem. Soc. 2015, 137, 3300;
- 5eW. Wagner, M. Wehner, V. Stepanenko, S. Ogi, F. Würthner, Angew. Chem. Int. Ed. 2017, 56, 16008;
- 5fT. Fukui, S. Kawai, S. Fujinuma, Y. Matsushita, T. Yasuda, T. Sakurai, S. Seki, M. Takeuchi, K. Sugiyasu, Nat. Chem. 2017, 9, 493.
- 6
- 6aX. Wang, G. Guerin, H. Wang, Y. Wang, I. Manners, M. A. Winnik, Science 2007, 317, 644;
- 6bZ. M. Hudson, D. J. Lunn, M. A. Winnik, I. Manners, Nat. Commun. 2014, 5, 3372.
- 7Z. M. Hudson, C. E. Boott, M. E. Robinson, P. A. Rupar, M. A. Winnik, I. Manners, Nat. Chem. 2014, 6, 893.
- 8
- 8aA. Sorrenti, J. Leira-Iglesias, A. J. Markvoort, T. F. A. de Greef, T. M. Hermans, Chem. Soc. Rev. 2017, 46, 5476;
- 8bM. J. Sun, Y. Liu, Y. Yan, R. Li, Q. Shi, Y. S. Zhao, Y. W. Zhong, J. Yao, J. Am. Chem. Soc. 2018, 140, 4269;
- 8cM. Hartlieb, E. D. H. Mansfield, S. Perrier, Polym. Chem. 2020, 11, 1083.
- 9W. Zhang, W. Jin, T. Fukushima, T. Mori, T. Aida, J. Am. Chem. Soc. 2015, 137, 13792.
- 10
- 10aX. Ma, Y. Zhang, Y. Zhang, Y. Liu, Y. Che, J. Zhao, Angew. Chem. Int. Ed. 2016, 55, 9539;
- 10bY. Liu, C. Peng, W. Xiong, Y. Zhang, Y. Gong, Y. Che, J. Zhao, Angew. Chem. Int. Ed. 2017, 56, 11380;
- 10cY. Gong, C. Cheng, H. Ji, Y. Che, L. Zang, J. Zhao, Y. Zhang, J. Am. Chem. Soc. 2022, 144, 15403.
- 11
- 11aK. Zhang, M. C. Yeung, S. Y. Leung, V. W. Yam, Proc. Natl. Acad. Sci. USA 2017, 114, 11844;
- 11bK. Zhang, M. C. L. Yeung, S. Y. L. Leung, V. W. W. Yam, Chem 2017, 2, 825.
- 12
- 12aQ. Wan, W.-P. To, C. Yang, C.-M. Che, Angew. Chem. Int. Ed. 2018, 57, 3089;
- 12bQ. Wan, X.-S. Xiao, W.-P. To, W. Lu, Y. Chen, K.-H. Low, C.-M. Che, Angew. Chem. Int. Ed. 2018, 57, 17189;
- 12cQ. Wan, J. Xia, W. Lu, J. Yang, C.-M. Che, J. Am. Chem. Soc. 2019, 141, 11572.
- 13B. Adelizzi, P. Chidchob, N. Tanaka, B. A. G. Lamers, S. C. J. Meskers, S. Ogi, A. R. A. Palmans, S. Yamaguchi, E. W. Meijer, J. Am. Chem. Soc. 2020, 142, 16681.
- 14
- 14aW. Wagner, M. Wehner, V. Stepanenko, F. Würthner, J. Am. Chem. Soc. 2019, 141, 12044;
- 14bW. Wagner, M. Wehner, V. Stepanenko, F. Würthner, CCS Chem. 2019, 1, 598.
- 15Q. Wan, W.-P. To, X. Chang, C.-M. Che, Chem 2020, 6, 945.
- 16
- 16aA. Sarkar, R. Sasmal, C. Empereur-Mot, D. Bochicchio, S. V. K. Kompella, K. Sharma, S. Dhiman, B. Sundaram, S. S. Agasti, G. M. Pavan, S. J. George, J. Am. Chem. Soc. 2020, 142, 7606;
- 16bA. Sarkar, T. Behera, R. Sasmal, R. Capelli, C. Empereur-Mot, J. Mahato, S. S. Agasti, G. M. Pavan, A. Chowdhury, S. J. George, J. Am. Chem. Soc. 2020, 142, 11528;
- 16cA. Sarkar, R. Sasmal, A. Das, S. S. Agasti, S. J. George, Chem. Commun. 2021, 57, 3937.
- 17A. Sarkar, R. Sasmal, A. Das, A. Venugopal, S. S. Agasti, S. J. George, Angew. Chem. Int. Ed. 2021, 60, 18209.
- 18
- 18aM. J. Sun, Y. W. Zhong, J. Yao, Angew. Chem. Int. Ed. 2018, 57, 7820;
- 18bM. J. Sun, Y. Liu, W. Zeng, Y. S. Zhao, Y. W. Zhong, J. Yao, J. Am. Chem. Soc. 2019, 141, 6157;
- 18cQ. Wan, K. Xiao, Z. Li, J. Yang, J. T. Kim, X. Cui, C.-M. Che, Adv. Mater. 2022, 34, e2204839;
- 18dS. Lei, J. Tian, Y. Kang, Y. Zhang, I. Manners, J. Am. Chem. Soc. 2022, 144, 17630;
- 18eQ. Wan, D. Li, J. Zou, T. Yan, R. Zhu, K. Xiao, S. Yue, X. Cui, Y. Weng, C.-M. Che, Angew. Chem. Int. Ed. 2022, 61, e202114323;
- 18fX. H. Jin, M. B. Price, J. R. Finnegan, C. E. Boott, J. M. Richter, A. Rao, S. M. Menke, R. H. Friend, G. R. Whittell, I. Manners, Science 2018, 360, 897;
- 18gJ. Tian, Y. Zhang, L. Du, Y. He, X. H. Jin, S. Pearce, J. C. Eloi, R. L. Harniman, D. Alibhai, R. Ye, D. L. Phillips, I. Manners, Nat. Chem. 2020, 12, 1150.
- 19
- 19aY. Chen, L. Zhang, L. Wang, L. Guo, C. Liu, Mater. Chem. Front. 2021, 5, 7808;
- 19bY. Chen, Z. Gao, L. Wang, J. Li, Y. Tang, C. Liu, ACS Appl. Polym. Mater. 2022, 4, 1055;
- 19cY. Chen, Y. Shi, Z. Gao, L. Wang, Y. Tang, J. Liu, C. Liu, Angew. Chem. Int. Ed. 2023, 62, e202302581.
- 20
- 20aA. Aliprandi, M. Mauro, L. De Cola, Nat. Chem. 2016, 8, 10;
- 20bS. Ogi, C. Grzeszkiewicz, F. Würthner, Chem. Sci. 2018, 9, 2768;
- 20cI. Helmers, G. Ghosh, R. Q. Albuquerque, G. Fernández, Angew. Chem. Int. Ed. 2021, 60, 4368.
- 21
- 21aJ. Matern, Z. Fernández, G. Fernández, Chem. Commun. 2022, 58, 12309;
- 21bL. Borsdorf, L. Herkert, N. Baumer, L. Rubert, B. Soberats, P. A. Korevaar, C. Bourque, C. Gatsogiannis, G. Fernández, J. Am. Chem. Soc. 2023, 145, 8882.
- 22Deposition number 2219728 (for 2) contains the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures service.
- 23S. Grimme, Angew. Chem. Int. Ed. 2008, 47, 3430–3434.
- 24
- 24aS. Datta, Y. Kato, S. Higashiharaguchi, K. Aratsu, A. Isobe, T. Saito, D. D. Prabhu, Y. Kitamoto, M. J. Hollamby, A. J. Smith, R. Dalgliesh, N. Mahmoudi, L. Pesce, C. Perego, G. M. Pavan, S. Yagai, Nature 2020, 583, 400;
- 24bN. Sasaki, M. F. J. Mabesoone, J. Kikkawa, T. Fukui, N. Shioya, T. Shimoaka, T. Hasegawa, H. Takagi, R. Haruki, N. Shimizu, S. I. Adachi, E. W. Meijer, M. Takeuchi, K. Sugiyasu, Nat. Commun. 2020, 11, 3578;
- 24cS. Sarkar, A. Sarkar, A. Som, S. S. Agasti, S. J. George, J. Am. Chem. Soc. 2021, 143, 11777;
- 24dR. Laishram, S. Sarkar, I. Seth, N. Khatun, V. K. Aswal, U. Maitra, S. J. George, J. Am. Chem. Soc. 2022, 144, 11306;
- 24eH. Itabashi, K. Tashiro, S. Koshikawa, S. Datta, S. Yagai, Chem. Commun. 2023, 59, 7375;
- 24fS. Sarkar, R. Laishram, D. Deb, S. J. George, J. Am. Chem. Soc. 2023, 145, 22009.
