Research Progress of Lewis Acid and Base Pairs Applied in Materials Chemistry

doi:10.6023/cjoc202301009

Abstract

Lewis Pairs (LPs) have made a rapid development in the fields of small molecule activation (such as CO₂, H₂, CO, SO₂, N₂O) and asymmetric catalysis, mainly thanks to the diversity of Lewis Pairs (LPs) synthesis and the convenient tunability of steric hindrance and electronic effects. The synthesis of novel functional polymer materials has always been a research hotspot in material chemistry. The introduction of Lewis acids (LAs) and Lewis bases (LBs) into the polymer skeleton can endow materials with unique properties and greatly enrich the types of functional polymer materials. Herein, this review summarizes the recent advance and synthesis of macro-LAs and macro-LBs, but also illustrates the diversity and versatility of LPs and Lewis pair polymerizations (LPPs) in the application of material chemistry. This review highlights the construction of supramolecular polymer networks, CO₂ capture and release, and the synthesis of novel topological polymers. In addition, the challenges and the future development trend in this field are also proposed.

Key words: Lewis pairs, Lewis pair polymerization, supramolecular polymer networks, CO₂ capture and release, topological polymer

Cite this article

Lijuan Xiao, Yanping Zhang, Miao Hong. Research Progress of Lewis Acid and Base Pairs Applied in Materials Chemistry[J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 949-960.

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Fig. & Tab. 14

Scheme 1. (A) Classical Lewis adduct (CLA), interacting Lewis pair (ILP) and frustrated Lewis pair (FLP), and (B) chain initiation and propagation in LPP

Scheme 2. (A) Reversible cross-linking based on dynamic interaction of the LP between silicone-boronate and aminosilicones, and (B) thermally reversible crosslinking between di-2-thienylboryl-substituted PS and pyridine-bearing telechelic PDMS

Scheme 3. Synthesis of LA functionalized polystyrene and LB functionalized PDMS and the formation of transient polymer networks

Scheme 4. Polymeric FLP based on phosphorous LB- and borane LA-functionalized polystyrene and the formation of a network gel by addition of cross-linking agent DEAD

Scheme 5. Preparation of a poly (FLP) crosslinking network by cycloether PSt-P and PSt-B

Scheme 6. Second-generation CO2-responsive system based on polymer-FLP (P1 and P2) Second-generation CO2-responsive system based on polymer-FLP (P1 and P2)

Scheme 7. Formation of dynamic CO2-cross-linked polymer networks based on trefoil-like frustrated Lewis pair

Scheme 8. Synthesis of poly(NHC) and poly(NHC)-catalyzed CO2 reduction to formamid with amine

Scheme 9. (A) Synthesis of poly(NHC) and the subsequent capture of CO2, and (B) synthesis of polyimidazole salt ionic liquid and the preparation of poly(NHC)-CO2 adduct (A) Synthesis of poly(NHC) and the subsequent capture of CO2, and (B) synthesis of polyimidazole salt ionic liquid and the preparation of poly(NHC)-CO2 adduct

Scheme 10. (A) Synthetic route to poly(RNHC) (R=iPr, nBu), and (B) polymeric Lewis adducts between the poly(N-heterocyclic carbene) [poly(NHC)] and C60

Scheme 11. (A) Synthetic routes of P3HT-(CH2)3-MIM and P3HT-(CH2)3-VIM, (B) linked D-A adduct of P3HT-(CH2)3-MIM-C60, and (C) the polymer brush of P[P3HT-(CH2)3-VIM-C60]

Scheme 12. Preparation of linear polymer brushes and bottle-brush brushes via LPP using SIP-initiating systems (A) the combination of self-assembled monolayers (SAMs) with NHO ends, (B) surface-attached macroinitiators bearing NHOs

Scheme 13. Synthesis of poly(NHO) and schematic diagram of molecular brush with side chain of P(δ-VL) and PMMA, respectively

Scheme 14. Preparation of PISA catalyzed by iBu2Al(BHT)/NHO via a one-pot reaction

References 68

[1]	Lewis, G. N. Valence and the Structure of Atoms and Molecules, Chemical Catalog Co., New York, 1923.
[2]	Welch, G. C.; Juan, R. R. S.; Masuda, J. D.; Stephan, D. W. Science 2006, 314, 1124. doi: 10.1126/science.1134230
[3]	Stephan, D. W. Acc. Chem. Res. 2015, 48, 306. doi: 10.1021/ar500375j
[4]	Stephan, D. W.; Erker, G. Angew. Chem., Int. Ed. 2015, 54, 6400. doi: 10.1002/anie.201409800
[5]	Scott, D. J.; Fuchter, M. J.; Ashley, A. E. Chem. Soc. Rev. 2017, 46, 5689. doi: 10.1039/C7CS00154A
[6]	Meng, W.; Feng, X.; Du, H. Acc. Chem. Res. 2018, 51, 191. doi: 10.1021/acs.accounts.7b00530
[7]	Hong, M.; Chen, J.; Chen, E. Y. X. Chem. Rev. 2018, 118, 10551. doi: 10.1021/acs.chemrev.8b00352
[8]	McGraw, M. L.; Chen, E. Y. X. Macromolecules 2020, 53, 6102. doi: 10.1021/acs.macromol.0c01156
[9]	Zhang, Y.; Miyake, G. M.; John, M. G.; Falivene, L.; Caporaso, L.; Cavallo, L.; Chen, E. Y. X. Dalton Trans. 2012, 41, 9119. doi: 10.1039/c2dt30427a
[10]	Jia, Y.-B.; Wang, Y.-B.; Ren, W.-M.; Xu, T.; Wang, J.; Lu, X.-B. Macromolecules 2014, 47, 1966. doi: 10.1021/ma500047d
[11]	McGraw, M. L.; Clarke, R. W.; Chen, E. Y. X. J. Am. Chem. Soc. 2020, 142, 5969. doi: 10.1021/jacs.0c01127
[12]	Wang, H.; Wang, Q.; He, J.; Zhang, Y. Polym. Chem. 2019, 10, 3597. doi: 10.1039/C9PY00427K
[13]	Zhang, Y.; Miyake, G. M.; Chen, E. Y. X. Angew. Chem., Int. Ed. 2010, 49, 10158. doi: 10.1002/anie.201005534
[14]	Wang, X.-J.; Hong, M. Angew. Chem., Int. Ed. 2020, 59, 2664. doi: 10.1002/anie.v59.7
[15]	Song, Y.; He, J.; Zhang, Y.; Gilsdorf, R. A.; Chen, E. Y. X. Nat. Chem. 2022, 15, 366. doi: 10.1038/s41557-022-01097-7
[16]	Zhao, W.; He, J.; Zhang, Y. Sci. Bull. 2019, 64, 1830. doi: 10.1016/j.scib.2019.08.025
[17]	Bai, Y.; Zhang, Y. Acta Polym. Sin. 2019, 50, 233. (in Chinese)
	(白云, 张越涛, 高分子学报, 2019, 50, 233.)
[18]	Xu, T.; Li, C. Prog. Chem. 2015, 27, 1087. (in Chinese)
	(徐铁齐, 李长宏, 化学进展, 2015, 27, 1087.) doi: 10.7536/PC150166
[19]	Xu, T.; Chen, E. Y. X. J. Am. Chem. Soc. 2014, 136, 1774. doi: 10.1021/ja412445n
[20]	Guan, Y.; Chang, K.; Sun, Q.; Xu, X. Chin. J. Org. Chem. 2022, 42, 1326. (in Chinese) doi: 10.6023/cjoc202112008
	(管怡雯, 常克俭, 孙千林, 徐信, 有机化学, 2022, 42, 1326.) doi: 10.6023/cjoc202112008
[21]	Wang, B.; Ji, H.; Li, Y. Acta Polym. Sin. 2020, 51, 1104. (in Chinese)
	(王彬, 季鹤源, 李悦生, 高分子学报, 2020, 51, 1104.)
[22]	Jia, Y.-G.; Jin, J.; Liu, S.; Ren, L.; Luo, J.; Zhu, X. X. Biomacromolecules 2018, 19, 626. doi: 10.1021/acs.biomac.7b01707
[23]	Yang, Y.; Urban, M. W. Adv. Mater. Interfaces 2018, 5, 1800384. doi: 10.1002/admi.v5.17
[24]	Yan, X.; Wang, F.; Zheng, B.; Huang, F. Chem. Soc. Rev. 2012, 41, 6042. doi: 10.1039/c2cs35091b
[25]	Cordier, P.; Tournilhac, F.; Soulié-Ziakovic, C.; Leibler, L. Nature 2008, 451, 977. doi: 10.1038/nature06669
[26]	Li, C.-H.; Zuo, J.-L. Adv. Mater. 2020, 32, 1903762.
[27]	Burattini, S.; Greenland, B. W.; Merino, D. H.; Weng, W.; Seppala, J.; Colquhoun, H. M.; Hayes, W.; Mackay, M. E.; Hamley, I. W.; Rowan, S. J. J. Am. Chem. Soc. 2010, 132, 12051. doi: 10.1021/ja104446r pmid: 20698543
[28]	Nakahata, M.; Takashima, Y.; Yamaguchi, H.; Harada, A. Nat. Commun. 2011, 2, 511. doi: 10.1038/ncomms1521 pmid: 22027591
[29]	Urban, M. W.; Davydovich, D.; Yang, Y.; Demir, T.; Zhang, Y.; Casabianca, L. Science 2018, 362, 220. doi: 10.1126/science.aat2975
[30]	Yolsal, U.; Horton, T. A. R.; Wang, M.; Shaver, M. P. Prog. Polym. Sci. 2020, 111, 101313. doi: 10.1016/j.progpolymsci.2020.101313
[31]	Hou, Q.; Liu, L.; Mellerup, S. K.; Wang, N.; Peng, T.; Chen, P.; Wang, S. Org. Lett. 2018, 20, 6467. doi: 10.1021/acs.orglett.8b02774
[32]	Mellerup, S. K.; Wang, S. Chem. Soc. Rev. 2019, 48, 3537. doi: 10.1039/c9cs00153k pmid: 31070642
[33]	Kristensen, T. E.; Hansen, T. Eur. J. Org. Chem. 2010, 2010, 3179.
[34]	Wang, M.; Nudelman, F.; Matthes, R. R.; Shaver, M. P. J. Am. Chem. Soc. 2017, 139, 14232. doi: 10.1021/jacs.7b07725
[35]	Dodge, L.; Chen, Y.; Brook, M. A. Chemistry 2014, 20, 9349.
[36]	Vidal, F.; Lin, H.; Morales, C.; Jäkle, F. Molecules 2018, 23, 405. doi: 10.3390/molecules23020405
[37]	Vidal, F.; Gomezcoello, J.; Lalancette, R. A.; Jäkle, F. J. Am. Chem. Soc. 2019, 141, 15963. doi: 10.1021/jacs.9b07452
[38]	Yolsal, U.; Horton, T. A. R.; Wang, M.; Shaver, M. P. J. Am. Chem. Soc. 2021, 143, 12980. doi: 10.1021/jacs.1c06408 pmid: 34387464
[39]	Birkmann, B.; Voss, T.; Geier, S. J.; Ullrich, M.; Kehr, G.; Erker, G.; Stephan, D. W. Organometallics 2010, 29, 5310. doi: 10.1021/om1003896
[40]	Chen, L.; Liu, R.; Yan, Q. Angew. Chem., Int. Ed. 2018, 57, 9336. doi: 10.1002/anie.201804034
[41]	Chen, L.; Liu, R.; Hao, X.; Yan, Q. Angew. Chem., Int. Ed. 2019, 58, 264. doi: 10.1002/anie.201812365
[42]	Stephan, D. W. Science 2016, 354, aaf7229.
[43]	Smith, C. A.; Narouz, M. R.; Lummis, P. A.; Singh, I.; Nazemi, A.; Li, C.-H.; Crudden, C. M. Chem. Rev. 2019, 119, 4986. doi: 10.1021/acs.chemrev.8b00514
[44]	Van Ausdall, B. R.; Glass, J. L.; Wiggins, K. M.; Aarif, A. M.; Louie, J. J. Org. Chem. 2009, 74, 7935. doi: 10.1021/jo901791k pmid: 19775141
[45]	Grossmann, A.; Enders, D. Angew. Chem., Int. Ed. 2012, 51, 314. doi: 10.1002/anie.201105415 pmid: 22121084
[46]	Holschumacher, D.; Bannenberg, T.; Hrib, C. G.; Jones, P. G.; Tamm, M. Angew. Chem., Int. Ed. 2008, 47, 7428. doi: 10.1002/anie.200802705 pmid: 18666192
[47]	Huang, K.; Zhang, J.-Y.; Liu, F.; Dai, S. ACS Catal. 2018, 8, 9079. doi: 10.1021/acscatal.8b02151
[48]	Zhang, Y.; Zhao, L.; Patra, P. K.; Hu, D.; Ying, J. Y. Nano Today 2009, 4, 13. doi: 10.1016/j.nantod.2008.10.015
[49]	Tan, M.; Zhang, Y.; Ying, J. Y. Adv. Synth. Catal. 2009, 351, 1390. doi: 10.1002/adsc.v351:9
[50]	Riduan, S. N.; Ying, J. Y.; Zhang, Y. J. Catal. 2016, 343, 46. doi: 10.1016/j.jcat.2015.09.009
[51]	Zhou, H.; Zhang, W.-Z.; Wang, Y.-M.; Qu, J.-P.; Lu, X.-B. Macromolecules 2009, 42, 5419. doi: 10.1021/ma901109j
[52]	Pinaud, J.; Vignolle, J.; Gnanou, Y.; Taton, D. Macromolecules 2011, 44, 1900. doi: 10.1021/ma1024285
[53]	Coupillaud, P.; Pinaud, J.; Guidolin, N.; Vignolle, J.; Fèvre, M.; Veaudecrenne, E.; Mecerreyes, D.; Taton, D. J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 4530. doi: 10.1002/pola.26869
[54]	Coupillaud, P.; Vignolle, J.; Mecerreyes, D.; Taton, D. Polymer 2014, 55, 3404. doi: 10.1016/j.polymer.2014.02.043
[55]	Hong, M.; Chen, E. Y.-X. Polym. Chem. 2015, 6, 1741. doi: 10.1039/C4PY01488J
[56]	Wang, Y.; Hong, M.; Bailey, T. S.; Chen, E. Y.-X. Molecules 2017, 22, 1564. doi: 10.3390/molecules22091564
[57]	Li, Z.; Tang, M.; Liang, S.; Zhang, M.; Biesold, G. M.; He, Y.; Hao, S.-M.; Choi, W.; Liu, Y.; Peng, J.; Lin, Z. Prog. Polym. Sci. 2021, 116, 101387. doi: 10.1016/j.progpolymsci.2021.101387
[58]	Verduzco, R.; Li, X.; Pesek, S. L.; Stein, G. E. Chem. Soc. Rev. 2015, 44, 2405. doi: 10.1039/c4cs00329b pmid: 25688538
[59]	Feng, C.; Li, Y.; Yang, D.; Hu, J.; Zhang, X.; Huang, X. Chem. Soc. Rev. 2011, 40, 1282. doi: 10.1039/B921358A
[60]	Pelras, T.; Mahon, C. S.; Müllner, M. Angew. Chem., Int. Ed. 2018, 57, 6982. doi: 10.1002/anie.v57.24
[61]	Xie, G.; Martinez, M. R.; Olszewski, M.; Sheiko, S. S.; Matyjaszewski, K. Biomacromolecules 2019, 20, 27. doi: 10.1021/acs.biomac.8b01171
[62]	Wang, Y.; Hong, M.; Bailey, T. S.; Chen, E. Y. X. Molecules 2017, 22, 1564. doi: 10.3390/molecules22091564
[63]	Wang, Q.; Zhao, W.; Zhang, S.; He, J.; Zhang, Y.; Chen, E. Y. X. ACS Catal. 2018, 8, 3571. doi: 10.1021/acscatal.8b00333
[64]	Bai, Y.; He, J.; Zhang, Y. Angew. Chem., Int. Ed. 2018, 57, 17230. doi: 10.1002/anie.v57.52
[65]	Wang, Q.; Zhao, W.; He, J.; Zhang, Y.; Chen, E. Y.-X. Macromolecules 2017, 50, 123. doi: 10.1021/acs.macromol.6b02398
[66]	Hou, L.; Liang, Y.; Wang, Q.; Zhang, Y.; Dong, D.; Zhang, N. ACS Macro Lett. 2018, 7, 65. doi: 10.1021/acsmacrolett.7b00903
[67]	Chen, S.; Hou, L.; Wang, Q.; Dong, D.; Zhang, N. Polym. Chem. 2018, 9, 5470. doi: 10.1039/C8PY01257A
[68]	Li, C.; Zhao, W.; He, J.; Zhang, Y.; Zhang, W. Angew. Chem., Int. Ed. 2022, 61, e202202448.

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