聚合诱导自组装制备多腔室囊泡以及成核链段中亲溶剂片段的影响

doi:10.6023/A22030128

摘要/Abstract

聚合物纳米材料的形貌对于其性能具有重要的影响, 其中囊泡(特别是多腔室囊泡)由于其具备空心结构备受关注. 聚合诱导自组装(PISA)是一种高效的制备聚合物纳米材料的方法. 然而, 目前利用PISA高效制备多腔室囊泡的报道则相对较少. 本工作中, 以聚乙二醇为大分子可逆加成-断裂链转移(RAFT)试剂(PEG₄₅-PETTC)调控苯乙烯(St)在混合溶剂乙醇/水(质量比7/3)中的RAFT聚合诱导自组装, 成功制备了多腔室囊泡. 同时开展了St和寡聚乙二醇甲醚甲基丙烯酸酯(OEGMA)的RAFT共聚合诱导自组装, 探索在成核链段中引入亲溶剂基元OEGMA对所得纳米材料形貌的影响. 由于聚苯乙烯的链刚性较强, 在聚苯乙烯链段中引入亲溶剂链段来增加成核链段的柔顺性是一种已报道的促进形貌转变的方法. 然而St和OEGMA在混合溶剂乙醇/水(质量比7/3)的聚合诱导自组装体系中, 发现亲溶剂基元(OEGMA)的引入, 导致所得纳米材料的形貌退化. 随着成核链段中亲溶剂基元的增加, 所得纳米材料逐渐由多腔室囊泡转变为单腔室囊泡和球形胶束.

关键词: 聚合诱导自组装, 多腔室囊泡, 形貌转变

The morphology of polymeric nano-objects has an important influence on its properties, among which vesicles (especially multi-chambered vesicles) have attracted much attention due to their hollow structures. Polymerization-induced self-assembly (PISA) is an efficient method for preparing polymeric nano-objects. However, there are relatively few reports on the efficient preparation of multi-chambered vesicles by PISA. In this paper, multi-chambered vesicles were successfully prepared by reversible addition-fragmentation chain transfer (RAFT) polymerization-induced self-assembly using styrene (St) as monomer, ethanol/water (7/3, mass ratio) as the solvent and polyethylene glycol (PEG₄₅-PETTC) as macro RAFT reagent. At the same time, RAFT copolymerization-induced self-assembly of St and oligoethylene glycol methyl ether methacrylate monomers (OEGMA) were carried out to explore the effect of introducing solvophilic moiety OEGMA into the core-forming blocks on the morphology of the resulting nano-objects. Due to the strong chain rigidity of polystyrene, the introduction of a solvophilic segment into the polystyrene segment to increase the flexibility of the core-forming blocks is a reported method to promote morphology evolution. However, in the polymerization-induced self-assembly system of St and OEGMA in ethanol/water (7/3, mass ratio), the introduction of solvophilic moieties (OEGMA) resulted in the morphology degradation of the resulting nano-objects. With the increase of solvophilic moieties in the core-forming blocks, the resulting nano-objects gradually transformed from multi-chambered vesicles to unicellular vesicles and spherical micelles. Random copolymer P(St-co-OEGMA) of the core-forming blocks in the corresponding nano-objects were formed by RAFT copolymerization of St and OEGMA. The solvated degree of the core-forming blocks increased due to the introduction of solvophilic OEGMA moieties. Moreover, the large side groups may also increase the free volume of core-forming blocks. The increasing of the free volume and solvated degree of the core-forming blocks synergistically weakened the packing strength of the core-forming blocks, leading to adversely effects on morphology transition of the nano-objects. We believe that the results of this study is a good complement to the current polymerization-induced self-assembly system.

Key words: polymerization-induced self-assembly, multi-chambered vesicles, morphology evolution

引用此文

Jamshid Kadirkhanov, 钟峰, 张文建, 洪春雁. 聚合诱导自组装制备多腔室囊泡以及成核链段中亲溶剂片段的影响[J]. 化学学报, 2022, 80(7): 913-920.

Jamshid Kadirkhanov, Feng Zhong, Wenjian Zhang, Chunyan Hong. Preparation of Multi-chambered Vesicles by Polymerization-induced Self-assembly and the Influence of Solvophilic Fragments in the Core-forming Blocks[J]. Acta Chimica Sinica, 2022, 80(7): 913-920.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

图/表 8

图式1. (A) PEG45-PETTC调控St在混合溶剂乙醇/水(质量比7/3)中的RAFT聚合诱导自组装制备多腔室囊泡. (B) St和OEGMA的RAFT共聚合诱导自组装体系中的形貌退化

Scheme 1. (A) Multi-chambered vesicles are prepared by polymerization-induced self-assembly (PISA) using PEG45-PETTC-mediated RAFT polymerization of styrene (St) in ethanol/water (7/3, mass ratio). (B) Morphology degradation in the PISA system of RAFT copolymerization of St and oligoethylene glycol methyl ether methacrylate (OEGMA)

图1. (A)大分子RAFT试剂PEG45-PETTC在CDCl3中的核磁共振氢谱(1H NMR). (B)大分子RAFT试剂PEG45-PETTC的凝胶渗透色谱(GPC)曲线

Figure 1. (A) 1H NMR spectra of the macro RAFT agent PEG45-PETTC in CDCl3. (B) GPC trace of the macro RAFT agent PEG45-PETTC

图2. St的RAFT聚合诱导自组装体系(St/PEG45-PETTC物质的量比600/1, 乙醇/水质量比7/3)中(A)单体转化率和聚合时间的关系图, (B) ln([M]0/[M]t)和聚合时间的关系图

Figure 2. (A) The curve of monomer conversion vs. polymerization time and (B) the curve of ln([M]0/[M]t) vs. polymerization time in the RAFT polymerization-induced self-assembly system with the feed molar ratio (600/1) of St/PEG45-PETTC and mass ratio (7/3) of ethanol/water as the solvent

图3. St的RAFT聚合体系中(St/PEG45-PETTC物质的量比600/1, 乙醇/水质量比7/3)不同的聚合时间所得PEG45-b-PSt纳米材料的TEM照片, (A) 12 h, (B) 15 h, (C) 18 h和(D) 24 h. 图片St下标的数字是此时的单体转化率. (E)为(D)的放大图

Figure 3. TEM images of the PEG45-b-PSt nano-objects obtained by RAFT polymerization of St in ethanol/water (7/3, mass ratio) with feed molar ratio (600/1) of St/PEG45-PETTC at different polymerization time, (A) 12 h, (B) 15 h, (C) 18 h and (D) 24 h. In the image, the subscript number of St is the monomer conversion at this time. (E) The magnified image of (D)

图4. St和OEGMA的RAFT共聚合体系中(St/OEGMA/PEG45-PETTC物质的量比600/10/1, 乙醇/水质量比7/3)不同的聚合时间所得PEG45-b-P(St-co-OEGMA)纳米材料的TEM照片, (A) 12 h和(B) 24 h. 图片上St代表苯乙烯, St的下标数字代表此时苯乙烯的转化率, O代表OEGMA, O的下标数字代表此时OEGMA的转化率

Figure 4. TEM images of the PEG45-b-P(St-co-OEGMA) nano-objects obtained by RAFT copolymerization of St and OEGMA in ethanol/water (7/3, mass ratio) with feed molar ratio (600/10/1) of St/OEGMA/ PEG45-PETTC at different polymerization time, (A) 12 h and (B) 24 h. St represents styrene, the subscript number of St is the conversion of styrene at this time, O represents OEGMA, and the subscript number of O is the conversion of OEGMA at this time

图5. 在混合溶剂乙醇/水(质量比7/3)中, St和OEGMA的RAFT共聚合在OEGMA/St/PEG45-PETTC不同物质的量比时所得PEG45-b-P(St-co- OEGMA)纳米材料的TEM照片, (A1) 10/300/1, (B1) 10/400/1, (C1) 10/500/1, (D1) 10/600/1, (A2) 30/300/1, (B2) 30/400/1, (C2) 30/500/1和(D2) 30/600/1. 图片上St代表苯乙烯, St的下标数字代表苯乙烯的转化率, O代表OEGMA, O的下标数字代表OEGMA的转化率

Figure 5. TEM images of the PEG45-b-P(St-co-OEGMA) nano-objects obtained by RAFT copolymerization of St and OEGMA in ethanol/water (7/3, mass ratio) with different feed molar ratio of St/OEGMA/PEG45-PETTC, (A1) 10/300/1, (B1) 10/400/1, (C1) 10/500/1, (D1) 10/600/1, (A2) 30/300/1, (B2) 30/400/1, (C2) 30/500/1 and (D2) 30/600/1. St represents styrene, the subscript number of St is the conversion of styrene, O represents OEGMA, and the subscript number of O is the conversion of OEGMA

图6. (A) St和OEGMA的RAFT共聚合在St/OEGMA/PEG45-PETTC物质的量比300/10/1时所得聚合物PEG45-b-P(St-co-OEGMA)的核磁共振氢谱. (B) St和OEGMA的RAFT共聚合在不同物质的量比St/OEGMA/PEG45-PETTC(黑色: 300/10/1, 红色: 400/10/1, 绿色: 500/10/1, 蓝色: 600/10/1)时所得聚合物PEG45-b-P(St-co-OEGMA)的GPC曲线. (C) St和OEGMA的RAFT共聚合在不同物质的量比St/OEGMA/PEG45-PETTC(黑色: 300/30/1, 红色: 400/30/1, 绿色: 500/30/1, 蓝色: 600/30/1)时所得聚合物PEG45-b-P(St-co-OEGMA)的GPC曲线

Figure 6. (A) The typical 1H NMR spectrum of PEG45-b-P(St-co-OEGMA) obtained by RAFT copolymerization of St and OEGMA at St/OEGMA/PEG45-PETTC (300/10/1, molar ratio). (B) GPC results of the PEG45-b-P(St-co-OEGMA) obtained by RAFT copolymerization of St and OEGMA at different feed molar ratio of St/OEGMA/PEG45-PETTC, black line: 300/10/1, red line: 400/10/1, green line: 500/10/1 and blue line: 600/10/1. (C) GPC results of the PEG45-b-P(St-co-OEGMA) obtained by RAFT copolymerization of St and OEGMA at different feed molar ratio of St/OEGMA/PEG45-PETTC, black line: 300/30/1, red line: 400/30/1, green line: 500/30/1 and blue line: 600/30/1

Sample^a	C_St^b	N_St^b	C_OEGMA^b	N_OEGMA^b	M_n^c	M_w/M_n^c	Morphology^d
OEGMA/St/PEG₄₅-PETTC (0/600/1)	87.8%	527	—	—	56100	1.21	mcv
OEGMA/St/PEG₄₅-PETTC (10/300/1)	96.1%	288	44.2%	4.4	31900	1.20	v
OEGMA/St/PEG₄₅-PETTC (10/400/1)	94.5%	378	25.9%	2.6	40600	1.21	v
OEGMA/St/PEG₄₅-PETTC (10/500/1)	95.2%	476	29.1%	2.9	50400	1.22	v
OEGMA/St/PEG₄₅-PETTC (10/600/1)	89.9%	539	38.9%	3.9	52000	1.24	v
OEGMA/St/PEG₄₅-PETTC (30/300/1)	83.2%	250	30.4%	9.1	29200	1.17	ir
OEGMA/St/PEG₄₅-PETTC (30/400/1)	89.6%	358	27.7%	8.3	41600	1.17	s
OEGMA/St/PEG₄₅-PETTC (30/500/1)	88.6%	443	24.5%	7.4	46500	1.18	s+v
OEGMA/St/PEG₄₅-PETTC (30/600/1)	86.6%	520	20.7%	6.2	53700	1.19	v
OEGMA/St/PEG₄₅-PETTC (50/600/1)	84.9%	509	19.0%	9.5	54100	1.26	s

表1. 不同OEGMA/St/PEG45-PETTC投料比的PISA体系中的单体转化率、疏溶剂链段中St和OEGMA的结构单元数量、所得聚合物PEG45-b-P(St-co-OEGMA)的分子量(Mn)和分子量分布(Mw/Mn)以及所得纳米材料的形貌

Table 1. The monomer conversion, number of St and OEGMA units in the solvophobic blocks, Mn and Mw/Mn of the resultant polymer PEG45-b-P(St-co-OEGMA), and morphology of the nano-objects obtained by PISA with different feed molar ratio of OEGMA/St/PEG45-PETTC

参考文献 73

[1]	Hu, X. L.; Zhang, Y. G.; Xie, Z. G.; Jing, X. B.; Bellotti, A.; Gu, Z. Biomacromolecules 2017, 18, 649. doi: 10.1021/acs.biomac.6b01704
[2]	Blackman, L. D.; Varlas, S.; Arno, M. C.; Houston, Z. H.; Fletcher, N. L.; Thurecht, K. J.; Hasan, M.; Gibson, M. I.; O'Reilly, R. K. ACS Central Sci. 2018, 4, 718. doi: 10.1021/acscentsci.8b00168 pmid: 29974067
[3]	Zhang, W. J.; Hong, C. Y.; Pan, C. Y. J. Mater. Chem. A 2014, 2, 7819. doi: 10.1039/c4ta00465e
[4]	Zhao, X.; Chen, M.; Zhang, W. G.; Wang, C. H.; Wang, F.; You, Y. Z.; Zhang, W. J.; Hong, C. Y. Macromol. Rapid Commun. 2020, 41, 2000260. doi: 10.1002/marc.202000260
[5]	Chang, J.; Zhang, W. J.; Hong, C. Y. Chin. J. Chem. 2017, 35, 1016. doi: 10.1002/cjoc.201600890
[6]	Zeng, M.; Zhou, S.; Sui, X. F.; Yuan, J. Y. Chin. J. Chem. 2021, 39, 3448. doi: 10.1002/cjoc.202100457
[7]	He, J.; Cao, J. P.; Chen, Y.; Zhang, L.; Tan, J. B. ACS Macro Lett. 2020, 9, 533. doi: 10.1021/acsmacrolett.0c00151
[8]	Luckerath, T.; Koynov, K.; Loescher, S.; Whitfield, C. J.; Nuhn, L.; Walther, A.; Barner-Kowollik, C.; Ng, D. Y. W.; Weil, T. Angew. Chem.-Int. Ed. 2020, 59, 15474. doi: 10.1002/anie.201916177
[9]	Shi, P.; Gao, C.; He, X.; Sun, P.; Zhang, W. Macromolecules 2015, 48, 1380. doi: 10.1021/acs.macromol.5b00021
[10]	Tan, J. B.; Liu, D. D.; Huang, C. D.; Li, X. L.; He, J.; Xu, Q.; Zhang, L. Macromol. Rapid Commun. 2017, 38, 1700195. doi: 10.1002/marc.201700195
[11]	Li, J. W.; Chen, M.; Zhang, Z.; Pan, C. Y.; Zhang, W. J.; Hong, C. Y. Polym. Chem. 2022, 13, 402. doi: 10.1039/D1PY01031J
[12]	Huo, M.; Du, H. T.; Zeng, M.; Pan, L.; Fang, T.; Xie, X. M.; Wei, Y.; Yuan, J. Y. Polym. Chem. 2017, 8, 2833. doi: 10.1039/C7PY00214A
[13]	Li, J. Y.; Qiu, L.; Xu, X. F.; Pan, C. Y.; Hong, C. Y.; Zhang, W. J. J. Mater. Chem. B 2018, 6, 1678. doi: 10.1039/C7TB02998E
[14]	Sun, X. L.; Liu, D. M.; Li, S. S.; Li, K. K.; Wan, W. M. Macromol. Rapid Commun. 2017, 38, 1700424. doi: 10.1002/marc.201700424
[15]	D'Agosto, F.; Rieger, J.; Lansalot, M.. Angew. Chem.-Int. Ed. 2020, 59, 8368. doi: 10.1002/anie.201911758
[16]	Khor, S. Y.; Quinn, J. F.; Whittaker, M. R.; Truong, N. P.; Davis, T. P. Macromol. Rapid Commun. 2019, 40, 1800438. doi: 10.1002/marc.201800438
[17]	Yeow, J.; Boyer, C. Adv. Sci. 2017, 4, 1700137. doi: 10.1002/advs.201700137
[18]	Zhang, Q. C.; Zeng, R. M.; Zhang, Y. X.; Chen, Y.; Zhang, L.; Tan, J. B. Macromolecules 2020, 53, 8982. doi: 10.1021/acs.macromol.0c01624
[19]	Zhang, W. J.; Kadirkhanov, J.; Wang, C. H.; Ding, S. G.; Hong, C. Y.; Wang, F.; You, Y. Z. Polym. Chem. 2020, 11, 3654. doi: 10.1039/D0PY00368A
[20]	Zhu, R. M.; Yang, C. L.; Chang, Z. X.; Pan, C. Y.; Zhang, W. J.; Hong, C. Y. Chin. J. Chem. 2022, 40, 453. doi: 10.1002/cjoc.202100665
[21]	Zhong, F.; Pan, C. Y. Macromol. Rapid Commun. 2021, 42, 2100566.
[22]	An, N. K.; Chen, X.; Yuan, J. Y. Polym. Chem. 2021, 12, 3220. doi: 10.1039/D1PY00216C
[23]	Shi, B. Y.; Wang, G. W. Acta Polym. Sin. 2022, 53, 15. (in Chinese)
	(史柏扬, 王国伟, 高分子学报, 2022, 53, 15.)
[24]	Cao, J. P.; Tan, Y. X.; Chen, Y.; Zhang, L.; Tan, J. B. Macromol. Rapid Commun. 2021, 42, 2100498. doi: 10.1002/marc.202100498
[25]	Jiang, J. H.; Zhu, Y. Q.; Du, J. Z. Acta Chim. Sinica 2020, 78, 719. (in Chinese) doi: 10.6023/A20050162
	(江金辉, 朱云卿, 杜建忠, 化学学报, 2020, 78, 719.) doi: 10.6023/A20050162
[26]	Li, S. Z.; Han, G.; Zhang, W. Q. Polym. Chem. 2020, 11, 4681. doi: 10.1039/D0PY00627K
[27]	Huang, J.; Guo, Y. K.; Gu, S.; Han, G.; Duan, W. F.; Gao, C. Q.; Zhang, W. Q. Polym. Chem. 2019, 10, 3426. doi: 10.1039/C9PY00452A
[28]	Gao, C. Q.; Zhou, H.; Qu, Y. Q.; Wang, W.; Khan, H.; Zhang, W. Q. Macromolecules 2016, 49, 3789. doi: 10.1021/acs.macromol.6b00688
[29]	Cheng, G.; Perez-Mercader, J. Macromol. Rapid Commun. 2019, 40, 1800513. doi: 10.1002/marc.201800513
[30]	Wang, X.; An, Z. S. Macromol. Rapid Commun. 2019, 40, 1800325. doi: 10.1002/marc.201800325
[31]	Wang, X.; Shen, L. L.; An, Z. S. Prog. Polym. Sci. 2018, 83, 1. doi: 10.1016/j.progpolymsci.2018.05.003
[32]	Chen, S. L.; Shi, P. F.; Zhang, W. Q. Chinese J. Polym. Sci. 2017, 35, 455. doi: 10.1007/s10118-017-1907-8
[33]	Chen, X.; Liu, L.; Huo, M.; Zeng, M.; Peng, L.; Feng, A.; Wang, X.; Yuan, J. Angew. Chem.-Int. Ed. 2017, 56, 16541. doi: 10.1002/anie.201709129
[34]	Sun, Y. J.; Cheng, X. X.; Miao, T. F.; Ma, H. T.; Zhang, W.; Zhu, X. L. Chinese J. Polym. Sci. 2022, 40, 56. doi: 10.1007/s10118-021-2647-3
[35]	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.202109084
[36]	Delaittre, G.; Dire, C.; Rieger, J.; Putaux, J. L.; Charleux, B. Chem. Commun. 2009, 2887.
[37]	Charleux, B.; Delaittre, G.; Rieger, J.; D'Agosto, F. Macromolecules 2012, 45, 6753. doi: 10.1021/ma300713f
[38]	Darabi, A.; Shirin-Abadi, A. R.; Jessop, P. G.; Cunningham, M. F. Macromolecules 2015, 48, 72. doi: 10.1021/ma502175c
[39]	Darabi, A.; Shirin-Abadi, A. R.; Pinaud, J.; Jessop, P. G.; Cunningham, M. F. Polym. Chem. 2014, 5, 6163. doi: 10.1039/C4PY00684D
[40]	Wan, W. M.; Pan, C. Y. Macromolecules 2007, 40, 8897. doi: 10.1021/ma0712854
[41]	Wang, J.; Wu, Z. G.; Wang, G. W.; Matyjaszewski, K. Macromol. Rapid Commun. 2019, 40, 1800332. doi: 10.1002/marc.201800332
[42]	Alzahrani, A.; Zhou, D. W.; Kuchel, R. P.; Zetterlund, P. B.; Aldabbagh, F. Polym. Chem. 2019, 10, 2658. doi: 10.1039/C9PY00498J
[43]	Zaquen, N.; Yeow, J.; Junkers, T.; Boyer, C.; Zetterlund, P. B. Macromolecules 2018, 51, 5165. doi: 10.1021/acs.macromol.8b00887
[44]	Wang, L.; Ding, Y.; Liu, Q. Z.; Zhao, Q. Q.; Dai, X. C.; Lu, X. H.; Cai, Y. L. ACS Macro Lett. 2019, 8, 623. doi: 10.1021/acsmacrolett.9600305
[45]	Ding, Y.; Cai, M.; Cui, Z.; Huang, L.; Wang, L.; Lu, X.; Cai, Y. Angew. Chem.-Int. Ed. 2018, 57, 1053. doi: 10.1002/anie.201710811
[46]	Kadirkhanov, J.; Yang, C. L.; Chang, Z. X.; Zhu, R. M.; Pan, C. Y.; You, Y. Z.; Zhang, W. J.; Hong, C. Y. Polym. Chem. 2021, 12, 1768. doi: 10.1039/D1PY00046B
[47]	Xu, X. F.; Zhu, R. M.; Pan, C. Y.; You, Y. Z.; Zhang, W. J.; Hong, C. Y. Macromolecules 2021, 54, 2729. doi: 10.1021/acs.macromol.0c02882
[48]	Zhao, W.; Gody, G.; Dong, S. M.; Zetterlund, P. B.; Perrier, S. Polym. Chem. 2014, 5, 6990. doi: 10.1039/C4PY00855C
[49]	Boott, C. E.; Gwyther, J.; Harniman, R. L.; Hayward, D. W.; Manners, I. Nat. Chem. 2017, 9, 785. doi: 10.1038/nchem.2721
[50]	Wang, J.; Cao, M. Y.; Zhou, P.; Wang, G. W. Macromolecules 2020, 53, 3157. doi: 10.1021/acs.macromol.0c00371
[51]	Zhou, C. C.; Wang, J.; Zhou, P.; Wang, G. W. Polym. Chem. 2020, 11, 2635. doi: 10.1039/D0PY00296H
[52]	Chen, J.; Sun, R. Y.; Liao, X. J.; Han, H. J.; Li, Y. W.; Xie, M. R. Macromolecules 2018, 51, 10202. doi: 10.1021/acs.macromol.8b01645
[53]	Le, D.; Dilger, M.; Pertici, V.; Diabate, S.; Gigmes, D.; Weiss, C.; Delaittre, G. Angew. Chem.-Int. Ed. 2019, 58, 4725. doi: 10.1002/anie.201813434
[54]	Varlas, S.; Foster, J. C.; Arkinstall, L. A.; Jones, J. R.; Keogh, R.; Mathers, R. T.; O'Reilly, R. K. ACS Macro Lett. 2019, 8, 466. doi: 10.1021/acsmacrolett.9b00117
[55]	Varlas, S.; Foster, J. C.; O'Reilly, R. K. Chem. Commun. 2019, 55, 9066. doi: 10.1039/C9CC04445K
[56]	Jiang, J. H.; Zhang, X. Y.; Fan, Z.; Du, J. Z. ACS Macro Lett. 2019, 8, 1216. doi: 10.1021/acsmacrolett.9b00606
[57]	Grazon, C.; Salas-Ambrosio, P.; Ibarboure, E.; Buol, A.; Garanger, E.; Grinstaff, M. W.; Lecommandoux, S.; Bonduelle, C. Angew. Chem.-Int. Ed. 2020, 59, 622. doi: 10.1002/anie.201912028
[58]	Wright, D. B.; Touve, M. A.; Adamiak, L.; Gianneschi, N. C. ACS Macro Lett. 2017, 6, 925. doi: 10.1021/acsmacrolett.7b00408
[59]	Zhu, A. D.; Guo, M. Y. Chinese J. Polym. Sci. 2016, 34, 367. doi: 10.1007/s10118-016-1748-x
[60]	Man, S. K.; Wang, X.; Zheng, J. W.; An, Z. S. Chinese J. Polym. Sci. 2020, 38, 9. doi: 10.1007/s10118-019-2303-3
[61]	Zheng, J. W.; Wang, X.; An, Z. S. Acta Polym. Sin. 2019, 50, 1167. (in Chinese)
	(郑晋文, 王晓, 安泽胜, 高分子学报, 2019, 50, 1167.)
[62]	Su, Z. P.; Tan, M. T.; Cao, Y. L.; Shi, Y.; Fu, Z. F. Acta Polym. Sin. 2019, 50, 808. (in Chinese)
	(苏志鹏, 谈梦婷, 曹艳玲, 石艳, 付志峰, 高分子学报, 2019, 50, 808.)
[63]	Lv, F.; An, Z. S.; Wu, P. Y. CCS Chem. 2020, 2, 2211.
[64]	Li, D.; Huo, M.; Liu, L.; Zeng, M.; Chen, X.; Wang, X. S.; Yuan, J. Y. Macromol. Rapid Commun. 2019, 40, 1900202. doi: 10.1002/marc.201900202
[65]	Li, J. W.; Chen, M.; Zhou, J. M.; Pan, C. Y.; Zhang, W. J.; Hong, C. Y. Polymer 2021, 221, 123589. doi: 10.1016/j.polymer.2021.123589
[66]	Guimaraes, T. R.; Bong, Y. L.; Thompson, S. W.; Moad, G.; Perrier, S.; Zetterlund, P. B. Polym. Chem. 2021, 12, 122. doi: 10.1039/D0PY01311K
[67]	Deane, O. J.; Musa, O. M.; Fernyhough, A.; Armes, S. P. Macromolecules 2020, 53, 1422. doi: 10.1021/acs.macromol.9b02394
[68]	Wen, S. P.; Saunders, J. G.; Fielding, L. A. Polym. Chem. 2020, 11, 3416. doi: 10.1039/C9PY01912J
[69]	Zhang, W. J.; Hong, C. Y.; Pan, C. Y. RSC Adv. 2015, 5, 42637. doi: 10.1039/C5RA05105C
[70]	Shi, P. F.; Zhou, H.; Gao, C. Q.; Wang, S.; Sun, P. C.; Zhang, W. Q. Polym. Chem. 2015, 6, 4911. doi: 10.1039/C5PY00697J
[71]	Yang, P. C.; Ratcliffe, L. P. D.; Armes, S. P. Macromolecules 2013, 46, 8545. doi: 10.1021/ma401797a
[72]	Zhou, J. M.; Zhang, W. J.; Hong, C. Y.; Pan, C. Y. Polym. Chem. 2016, 7, 3259. doi: 10.1039/C6PY00164E
[73]	Wan, W. M.; Hong, C. Y.; Pan, C. Y. Chem. Commun. 2009, 39, 5883.