Synthesis and Structure Control of Chiral Helical Polymers

doi:10.6023/cjoc202305003

Abstract

Many researches have been done on artificial chiral helical polymers whose helical senses are excess because of their wide applications such as enantiomeric separation, photoelectric functional materials, and so on. Synthetic optically active helical polymers can be generally divided into static helical polymers and dynamic helical polymers on the basis of whether the helix inversion barriers are high or low. Among the three different kinds of helical polymers, polyisocyanates, polyisocyanides and polyacetylenes were mainly discussed in this review. And this review mainly focuses on the methods such as polymerization of chiral monomer, helix-sense-selective polymerization, chirality induction, chiral amplification, cis-cisoid to cis-transoid, polymerization-induced chiral self-assembly etc.

Key words: optically active helical polymer, polymerization of chiral monomer, helix-sense-selective polymerization, chirality induction, chiral amplification

Cite this article

Qian Wang, Yuqi Liu, Zongquan Wu. Synthesis and Structure Control of Chiral Helical Polymers[J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4141-4146.

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Fig. & Tab. 4

Figure 1. Chiral materials in nature

Figure 2. Transmission of stereochemical information from helical side chain to helical main chain on nanometer scale in chiral PPA-g-PHIC graft copolymer. Reproduced with permission.[17] Copyright (2014) American Chemical Society

Figure 3. Reported catalysts for isocyanide polymerization. Reproduced with permission[18] (a) Copyright (2021) American Chemical Society; (b) copyright (2022) Royal Society of Chemistry

Figure 4. Chiral gels formed by “helix-sense-selective polymerization” combining with “chiral amplification” Reproduced with permission.[47] Copyright (2016) American Chemical Society.

References 55

[1]	Watso J. D.; Crick H. C. Nature 1953, 171, 737. doi: 10.1038/171737a0
[2]	Shen J.; Okamoto Y. Chem. Rev. 2016, 116, 1094. doi: 10.1021/acs.chemrev.5b00317 pmid: 26402470
[3]	(a) Bak I. G.; Chae C.; Lee J.-S. Macromolecules 2022, 55, 1923. doi: 10.1021/acs.macromol.1c02160
	(b) Song L.-F.; Zhou Y.-Y.; Gao T.; Yan P.-F.; Li H.-F. Acta Chim. Sinica 2021, 79, 1042. (in Chinese) doi: 10.6023/A21040185
	(宋龙飞, 周妍妍, 高婷, 闫鹏飞, 李洪峰, 化学学报, 2021, 79, 1042.) doi: 10.6023/A21040185
	(c) Zhai X.-Y.; Wang X.-Q.; Wu B.; Zhou Y.-G. Chin. J. Chem. 2022, 40, 21. doi: 10.1002/cjoc.v40.1
[4]	(a) Liu J.-Z.; Lam J. W. Y.; Tang B.-Z. Chem. Rev. 2009, 109, 5799. doi: 10.1021/cr900149d pmid: 11740926
	(b) Nakano T.; Okamoto Y. Chem. Rev. 2001, 101, 4013. pmid: 11740926
	(c) Cornelissen J. J. L. M.; Rowan A. E.; Nolte R. J. M.; Sommerdijk C N. A. J. M. Chem. Rev. 2001, 101, 4039. pmid: 11740926
[5]	Hanes C. S. New Phytol. 1937, 36, 189. doi: 10.1111/nph.1937.36.issue-3
[6]	Pauling L.; Corey R. B.; Branson H. R. Proc. Natl. Acad. Sci. U. S. A. 1951, 378, 205.
[7]	Watson J. D.; Crick F. H. C. Nature 1953, 171, 737. doi: 10.1038/171737a0
[8]	Natta G.; Pino P.; Corradini P.; Danusso F.; Mantica E.; Nazzanti G.; Moraglio G. J. Am. Chem. Soc. 1955, 77, 1708. doi: 10.1021/ja01611a109
[9]	(a) Pino P.; Lorenzi G. P. J. Am. Chem. Soc. 1960, 82, 4745.
[10]	(a) Rowan A. E.; Nolte R. J. M. Angew. Chem., Int. Ed. 1998, 37, 63. pmid: 11740925
	(b) Cornelissen J. J. L. M.; Rowan A. E.; Nolte R. J. M.; Sommerdijk N. A. J. M. Chem. Rev. 2001, 101, 4039. pmid: 11740925
	(c) Okamoto Y.; Nakano T. Chem. Rev. 1994, 94, 349. doi: 10.1021/cr00026a004 pmid: 11740925
	(d) Nakano T.; Okamoto Y. Chem. Rev. 2001, 101, 4013. pmid: 11740925
	(e) Green M. M.; Peterson N. C.; Sato T.; Teramoto A.; Cook R.; Lifson S. Science 1995, 268, 1860. pmid: 11740925
	(f) Fujiki M. Macromol. Rapid Commun. 2001, 22, 539. doi: 10.1002/1521-3927(20010501)22:8【-逻辑与-】lt;539::AID-MARC539【-逻辑与-】gt;3.0.CO;2-K pmid: 11740925
	(g) Wulff G. Angew. Chem., nt. Ed. Engl. 1989, 28, 21. pmid: 11740925
	(h) Pu L. Acta Polym. 1997, 48, 116. doi: 10.1002/actp.01.v48:4 pmid: 11740925
	(i) Maeda K.; Yashima E. Top. Curr. Chem. 2006, 265, 47. pmid: 11740925
	(j) Nakano T.; Okamoto Y. Chem. Rev. 2001, 101, 4013. pmid: 11740925
[11]	Okamoto Y.; Suzuki K.; Ohta K.; Hatada K.; Yuki H. J. Am. Chem. Soc. 1979, 101, 4763. doi: 10.1021/ja00510a072
[12]	Green M. M.; Andreola C.; Muñoz B.; Reidy M. P. J. Am. Chem. Soc. 1988, 110, 4063. doi: 10.1021/ja00220a070
[13]	(a) Goodman M.; Chen S.-C. Macromolecules 1970, 3, 398. doi: 10.1021/ma60016a005
	(b) Goodman M.; Chen S.-C. Macromolecules 1971, 4, 625. doi: 10.1021/ma60023a023
[14]	(a) Green M. M.; Gross R. A.; Crosby III C.; Schilling F. C. Macromolecules 1987, 20, 992. doi: 10.1021/ma00171a019
	(b) Hino K.; Maeda K.; Okamoto Y. J. Phys. Org. Chem. 2000, 13, 361. doi: 10.1002/(ISSN)1099-1395
	(c) Shin Y.-D.; Ahn J.-H.; Lee J.-S. Macromol. Rapid Commun. 2001, 22, 1041. doi: 10.1002/(ISSN)1521-3927
[15]	(a) Green M. M.; Andreola C.; Peterson N. C. J. Am. Chem. Soc. 1989, 111, 8850. doi: 10.1021/ja00206a013
	(b) Gu H.; Nakamura H.; Sato T.; Teramoto A.; Green M. M.; Andreola C.; Peterson N. C.; Lifson S. Macromolecules 1995, 28, 1016. doi: 10.1021/ma00108a032
	(c) Green M. M.; Garetz B. A.; Munoz B.; Chang H. P.; Hoke S.; Cooks R. G. J. Am. Chem. Soc. 1995, 117, 4181. doi: 10.1021/ja00119a039
[16]	Maeda K.; Okamoto Y. Polym. J. 1998, 30, 100. doi: 10.1295/polymj.30.100
[17]	(a) Chae C.-G.; Bak I. G.; Lee J.-S. Macromolecules 2018, 51, 6771. doi: 10.1021/acs.macromol.8b01458
	(b) Shan P. N.; Chae C.-G.; Min J.; Shimada R.; Satoh T.; Kakuchi T.; Lee J.-S. Macromolecules 2014, 47, 2796. doi: 10.1021/ma500544b
[18]	Millich F. Adv. Polym. Sci. 1975, 19, 117.
[19]	(a) Drenth W.; Nolte R. J. M. Acc. Chem. Res. 1979, 12, 30. doi: 10.1021/ar50133a005
	(b) Kamer P. C. J.; Nolte R. J. M.; Drenth W. J. Am. Chem. Soc. 1988, 110, 6818. doi: 10.1021/ja00228a035
[20]	Wada Y.; Shinohara K.; Asakawa H.; Matsui S.; Taima T.; Ikai T. J. Am. Chem. Soc. 2019, 141, 13995. doi: 10.1021/jacs.9b07417
[21]	Wu Z.-Q.; Nagai K.; Banno M.; Okoshi K.; Onitsuka K.; Yashima E. J. Am. Chem. Soc. 2009, 131, 6708. doi: 10.1021/ja900036n
[22]	Xue Y.-X.; Zhu Y. -Y.; Gao L.-M.; He X.-Y.; Liu N.; Zhang W.-Y.; Yin J.; Ding Y.-S.; Zhou H.-P.; Wu Z.-Q. J. Am. Chem. Soc. 2014, 136, 4706. doi: 10.1021/ja5004747
[23]	Yang L.; Tang Y.; Liu N.; Liu C.-H.; Ding Y.-S.; Wu Z.-Q. Macromolecules 2016, 49, 7692. doi: 10.1021/acs.macromol.6b01870
[24]	Jiang Z.-Q.; Zhao S.-Q.; Su Y.-X.; Liu N.; Wu Z.-Q. Macromolecules 2018, 51, 737. doi: 10.1021/acs.macromol.7b02663
[25]	Wang Q.; Chu B.-F.; Chu J.-H.; Liu N.; Wu Z.-Q. ACS Macro Lett. 2018, 7, 127. doi: 10.1021/acsmacrolett.7b00875
[26]	Xu L.; Yang L.; Guo Z.-X.; Liu N.; Zhu Y. -Y.; Li Z. B.; Wu Z.-Q. Macromolecules 2019, 52, 5698. doi: 10.1021/acs.macromol.9b00926
[27]	Zhao S.-Q.; Hu G.-J.; Xu X.-H.; Kang S.-M.; Liu N.; Wu Z.-Q. ACS Macro Lett. 2018, 7, 1073. doi: 10.1021/acsmacrolett.8b00610
[28]	Chen J.-L.; Yang L.; Wang Q.; Jiang Z.-Q.; Liu N.; Yin J.; Ding Y.-S.; Wu Z.-Q. Macromolecules 2015, 48, 7737. doi: 10.1021/acs.macromol.5b02124
[29]	Wang Q.; Xiao J.; Su Y.-H.; Huang J.-W.; Li J.-H.; Qiu L.-G.; Zhan M.-X.; He X.; Yuan W.-Z.; Li Y. Polym. Chem. 2021, 12, 2132. doi: 10.1039/D1PY00022E
[30]	Huang J.; Shen L.; Zou H.; Liu N. Chin. J. Polym. Sci. 2018, 36, 799. doi: 10.1007/s10118-018-2136-5
[31]	Imai T.; Hayakawa K.; Satoh T.; Kaga H.; Kakuchi T. J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 3443. doi: 10.1002/pola.v40:20
[32]	Kanbayashi N.; Tokuhara S.; Sekine T.; Kataoka Y.; Okamura T.; Onitsuka K. J. Polym. Sci., Part A: Polym. Chem. 2018, 56, 496. doi: 10.1002/pola.v56.5
[33]	Xu L.; Xu X.-H.; Liu N.; Zou H.; Wu Z.-Q. Macromolecules 2018, 51, 7546. doi: 10.1021/acs.macromol.8b01478
[34]	(a) Yashima E.; Maeda K.; Okamoto Y. Nature (London) 1999, 399, 449. doi: 10.1038/20900
	(b) Maeda K.; Morino K.; Okamoto Y.; Sato T.; Yashima E. J. Am. Chem. Soc. 2004, 126, 4329. doi: 10.1021/ja0318378
[35]	Maeda K.; Muto M.; Sato T.; Yashima E. Macromolecules 2011, 44, 8343. doi: 10.1021/ma201913g
[36]	Maeda K.; Nozaki M.; Hashimoto K.; Shimomura K.; Hirose D.; Nishimura T.; Watanabe G.; Yashima E. J. Am. Chem. Soc. 2020, 142, 7668. doi: 10.1021/jacs.0c02542
[37]	Kakuchi R.; Sakai R.; Otsuka I.; Kaga H.; Kakuchi T. Macromolecules 2005, 38, 9441. doi: 10.1021/ma051824+
[38]	(a) Aoki T.; Kaneko T.; Maruyama N.; Sumi A.; Takahashi M.; Sato T.; Teraguchi M. J. Am. Chem. Soc. 2003, 125, 6346. doi: 10.1021/ja021233o
	(b) Teraguchi M.; Tanioka D.; Kaneko T.; Aoki T. ACS Macro Lett. 2012, 1, 1258. doi: 10.1021/mz300309c
[39]	Wang S.; Chen J.-X.; Feng X.-Y.; Shi G.; Zhang J.; Wan X.-H. Macromolecules 2017, 50, 4610. doi: 10.1021/acs.macromol.7b01028
[40]	(a) Ishidate R.; Markvoort A. J.; Maeda K.; Yashima E. J. Am. Chem. Soc. 2019, 141, 7605. doi: 10.1021/jacs.9b02904 pmid: 31017424
	(b) Ikai T.; Ishidate R.; Inoue K.; Kaygisiz K.; Maeda K.; Yashima E. Macromolecules 2020, 53, 973. doi: 10.1021/acs.macromol.9b02727 pmid: 31017424
	(c) Ikai T.; Takeda S.; Yashima E. ACS Macro Lett. 2022, 11, 525. doi: 10.1021/acsmacrolett.2c00136 pmid: 31017424
[41]	(a) Li B.-S.; Lam J. W. Y.; Yu Z.-Q.; Tang B.-Z. Langmuir 2012, 28, 5770. doi: 10.1021/la300061u
	(b) Jim C. K. W.; Lam J. W. Y.; Leung C. W. T.; Qin A.-J.; Mahtab F.; Tang B.-Z. Macromolecules 2011, 44, 2427. doi: 10.1021/ma200075y
[42]	(a) Xia Q.; Meng L.-M.; He T. C.; Huang G. X.; Li B. S.; Tang B. Z. ACS Nano 2021, 15, 4956. doi: 10.1021/acsnano.0c09802
	(b) Song F.; Cheng Y.; Liu Q.; Qiu Z.; Lam J. W. Y.; Lin L.; Yang F.; Tang B. Z. Mater. Chem. Front. 2019, 3, 1768. doi: 10.1039/C9QM00332K
	(c) Zhao D.; He H.; Gu X.; Guo L.; Wong K. S.; Lam J. W. Y.; Tang B.-Z. Adv. Opt. Mater. 2016, 4, 534. doi: 10.1002/adom.v4.4
[43]	(a) Wang S.; Hu D.-P.; Guan X.-Y.; Cai S.-L.; Shi G.; Shuai Z.-G.; Zhang J.; Peng Q.; Wan X.-H. Angew. Chem., Int. Ed. 2021, 60, 21918. doi: 10.1002/anie.v60.40
	(b) Wang S.; Xie S.-Y.; Zeng H.; Du H.-X.; Zhang J.; Wan X.-H. Angew. Chem., Int. Ed. 2022, 61, e202202268. doi: 10.1002/anie.v61.23
	(c) Chen J.-X.; Cai S.-L.; Wang R.; Wang S.; Zhang J.; Wan X.-H. Macromolecules 2020, 53, 1638. doi: 10.1021/acs.macromol.9b02504
	(d) Cai S.-L.; Chen J.-X.; Wang S.; Zhang J.; Wan X.-H. Angew. Chem., Int. Ed. 2021, 60, 9686. doi: 10.1002/anie.v60.17
[44]	(a) Rodríguez R.; Quiñoa E.; Riguera R.; Freire F. J. Am. Chem. Soc. 2016, 138, 9620. doi: 10.1021/jacs.6b04834 pmid: 27419262
	(b) Cobos K.; Rodríguez R.; Domarco O.; Fernandez B.; Quinoa E.; Riguera R.; Freire F. Macromolecules 2020, 53, 3182. doi: 10.1021/acs.macromol.0c00085 pmid: 27419262
[45]	(a) Jia H.-G.; Teraguchi M.; Aoki T.; Abe Y.; Kaneko T.; Hadano S.; Namikoshi T.; Marwanta E. Macromolecules 2009, 42, 17. doi: 10.1021/ma802313z
	(b) Teraguchi M.; Tanioka D.; Kaneko T.; Aoki T. ACS Macro Lett. 2012, 1, 1258. doi: 10.1021/mz300309c
[46]	Zhang Y.-J.; Kang L.; Huang H.-J.; Deng J.-P. ACS Appl. Mater. Interfaces 2020, 12, 6319. doi: 10.1021/acsami.9b21222
[47]	Huang H.-J.; Deng J.-P.; Shi Y. Macromolecules 2016, 49, 2948. doi: 10.1021/acs.macromol.6b00612
[48]	(a) Matyjaszewski K. J. Inorg. Organomet. Polym. 1992, 2, 5. doi: 10.1007/BF00696533
	(b) Fujiki M. J. Am. Chem. Soc. 1994, 116, 6017. doi: 10.1021/ja00092a082
	(c) Frey H.; Moeller M.; Matyjaszewski K. Macromolecules 1994, 27,1814. doi: 10.1021/ma00085a022
	(d) Fujiki M.; Koe J. R.; Terao K.; Sato T.; Teramoto A.; Watanabe J. Polym. J. 2003, 35, 297. doi: 10.1295/polymj.35.297
[49]	Zhao Y.; Chen H.-L.; Yin L.; Cheng X.-X.; Zhang W.; Zhu X.-L. Polym. Chem. 2018, 9, 2295. doi: 10.1039/C8PY00114F
[50]	(a) Cheng X.-X.; Miao T.-F.; Yin L.; Ji Y.-J.; Li Y.-Y.; Zhang Z.-B.; Zhang W.; Zhu X.-L. Angew. Chem., Int. Ed. 2020, 59, 9669. doi: 10.1002/anie.v59.24
	(b) Cheng X.-X.; Miao T.-F.; Ma Y.-F.; Zhu X.-Y.; Zhang W.; Zhu X.-L. Angew. Chem., Int. Ed. 2021, 60, 24430. doi: 10.1002/anie.v60.46
	(c) Gan Y.-J.; Dai H.-B.; Ma Y.-F.; Cheng X.-X.; Wang Z.; Zhang W. Macromolecules 2022, 55, 8556. doi: 10.1021/acs.macromol.2c01454
[51]	Shen J.; Okamoto Y. Chem. Rev. 2016, 116, 1094. doi: 10.1021/acs.chemrev.5b00317 pmid: 26402470
[52]	Kan K.; Fujiki M.; Akashi M. ACS Macro Lett. 2016, 5, 1014. doi: 10.1021/acsmacrolett.6b00513
[53]	Ho R M.; Chen C.-K.; Chiang Y.-W. Adv. Mater. 2010, 18, 2355. doi: 10.1002/adma.v18:18
[54]	Liang J.-Y.; Yang B.-W.; Deng J.-P. Chem. Eng. J. 2018, 344, 262. doi: 10.1016/j.cej.2018.03.076
[55]	O‘Leary L. E. R.; Fallas J. A.; Bakota E. L. Nat. Chem. 2011, 3, 821. doi: 10.1038/nchem.1123

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