Chinese Journal of Organic Chemistry >
Synthesis and Photo-responsive Self-Assembly of Azobenzene-Containing Molecular Brushes
Received date: 2021-02-25
Revised date: 2021-03-25
Online published: 2021-04-29
Supported by
National Natural Science Foundation of China(52073092); National Natural Science Foundation of China(51873061); National Natural Science Foundation of China(22001072)
Molecular brushes (MBs) are a unique type of branched macromolecules which graft polymeric chains onto a linear polymeric backbone densely. Crowded tethered side chains generate strong steric repulsion and force the backbone to stretch out, resulting in a persistent cylindrical shape and low density of entanglements of brushes. Owing to the unique rheological and mechanical properties and self-assembly behaviors, MBs show a great potential in nanotechnology and surface science. Herein, the synthesis of novel MBs of polyacrylate-g-poly(6-(4-butyl-4'-oxyazobenzene)hexylacrylate)/barbituric acid (PA-g-PAzo/Bar) was reported, in which PAzo brushes and hydrogen-bonding barbituric acid were grafted using the combination of concurrent atom transfer radical polymerization (ATRP) and click reaction. MBs-based aggregates change from cylinder to compound micelle by increasing the concentration. It is interesting that morphology transitions of cylinder-to-porous nanosheet and compound micelle-to-pearl-necklace were observed upon UV irradiation, that was ascribed to thetrans-to-cis isomerization of PAzo brushes.
Hongyu Qian , Pin He , Lu Zhang , Ke Chen , Binbin Xu , Shaoliang Lin . Synthesis and Photo-responsive Self-Assembly of Azobenzene-Containing Molecular Brushes[J]. Chinese Journal of Organic Chemistry, 2021 , 41(7) : 2891 -2897 . DOI: 10.6023/cjoc202102047
| [1] | Cabral, H.; Miyata, K.; Osada, K.; Kataoka, K. Chem. Rev. 2018, 118,6844. |
| [2] | Mai, Y.; Eisenberg, A. Chem. Soc. Rev. 2012, 41,5969. |
| [3] | Zhang, K.; Jiang, M.; Chen, D. Prog. Polym. Sci. 2012, 37,445. |
| [4] | Hayward,R. C.; Pochan,D. J. Macromolecules 2010, 43,3577. |
| [5] | Tao, D.; Feng, C.; Cui, Y.; Yang, X.; Manners, I.; Winnik,M. A.; Huang, X. J. Am. Chem. Soc. 2017, 139,7136. |
| [6] | Tao, D.; Feng, C.; Lu, Y.; Cui, Y.; Yang, X.; Manners, I.; Winnik,M. A.; Huang, X. Macromolecules 2018, 51,2065. |
| [7] | Wu, J.; Liu, Z.; Yao, Y.; Lin, S. Chin. J. Org. Chem. 2019, 39,2952 (in Chinese). |
| [7] | ( 吴嘉诚, 刘争卉, 姚远, 林绍梁, 有机化学, 2019, 39,2952.) |
| [8] | Lutz,J. -F.; Lehn,J. -M.; Meijer,E. W.; Matyjaszewski, K. Nat. Rev. Mater. 2016, 1,16024. |
| [9] | Matyjaszewski, K. Science 2011, 333,1104. |
| [10] | Polymeropoulos, G.; Zapsas, G.; Ntetsikas, K.; Bilalis, P.; Gnanou, Y.; Hadjichristidis, N. Macromolecules 2017, 50,1253. |
| [11] | Gregory, A.; Stenzel,M. H. Prog. Polym. Sci. 2012, 37,38. |
| [12] | Que, Y.; Liu, Y.; Tan, W.; Feng, C.; Shi, P.; Li, Y.; Huang, X. ACS Macro Lett. 2016, 5,168. |
| [13] | Ju, M.; Xu, B.; Xu, L. Chin. J. Org. Chem. 2020, 40,4344 (in Chinese). |
| [13] | ( 鞠明杰, 徐彬彬, 徐立功, 有机化学, 2020, 40,4344.) |
| [14] | Xie, G.; Martinez,M. R.; Olszewski, M.; Sheiko,S. S.; Matyjaszewski, K. Biomacromolecules 2019, 20,27. |
| [15] | Feng, C.; Huang, X. Acc. Chem. Res. 2018, 51,2314. |
| [16] | Xu, B.; Feng, C.; Hu, J.; Shi, P.; Gu, G.; Wang, L.; Huang, X. ACS Appl. Mater. Interfaces 2016, 8,6685. |
| [17] | Xu, B.; Liu, Y.; Sun, X.; Hu, J.; Shi, P.; Huang, X. ACS Appl. Mater. Interfaces 2017, 9,16517. |
| [18] | Cai, X.; Hu, W.; Lu, G.; Huang, X. Chin. J. Org. Chem. 2013, 33,2520 (in Chinese). |
| [18] | ( 蔡晓冰, 胡薇, 陆国林, 黄晓宇, 有机化学, 2013, 33,2520.) |
| [19] | Wang, W.; Shen, D.; Li, X.; Yao, Y.; Lin, J.; Wang, A.; Yu, J.; Wang,Z. L.; Hong,S. W.; Lin, Z.; Lin, S. Angew. Chem. Int. Ed. 2018, 57,2139. |
| [20] | Liu, M.; Liu, H.; Yan, D.; Zhang, Z.; Guan, J. Chin. J. Org. Chem. 2020, 40,125 (in Chinese). |
| [20] | ( 刘曼曼, 刘豪浩, 鄢道仁, 张智勇, 关金涛, 有机化学, 2020, 40,125.) |
| [21] | Cheng, X.; Miao, T.; Yin, L.; Ji, Y.; Li, Y.; Zhang, Z.; Zhang, W.; Zhu, X. Angew. Chem. Int. Ed. 2020, 59,9669. |
| [22] | Huang, S.; Chen, Y.; Ma, S.; Yu, H. Angew. Chem. Int. Ed. 2018, 57,12524. |
| [23] | Xu, B.; Qian, H.; Lin, S. ACS Macro Lett. 2020, 9,404. |
| [24] | Xu, B.; Feng, C.; Huang, X. Nat. Commun. 2017, 8,333. |
| [25] | Datta, S.; Kato, Y.; Higashiharaguchi, S.; Aratsu, K.; Isobe, A.; Saito, T.; Prabhu,D. D.; Kitamoto, Y.; Hollamby,M. J.; Smith,A. J.; Dalgliesh, R.; Mahmoudi, N.; Pesce, L.; Perego, C.; Pavan,G. M.; Yagai, S. Nature 2020, 583,400. |
| [26] | Yagai, S.; Goto, Y.; Lin, X.; Karatsu, T.; Kitamura, A.; Kuzuhara, D.; Yamada, H.; Kikkawa, Y.; Saeki, A.; Seki, S. Angew. Chem. Int. Ed. 2012, 51,6643. |
| [27] | Adhikari, B.; Yamada, Y.; Yamauchi, M.; Wakita, K.; Lin, X.; Aratsu, K.; Ohba, T.; Karatsu, T.; Hollamby,M. J.; Shimizu, N.; Takagi, H.; Haruki, R.; Adachi, S.; Yagai, S. Nat. Commun. 2017, 8,15254. |
| [28] | Prabhu,D. D.; Aratsu, K.; Kitamoto, Y.; Ouchi, H.; Ohba, T.; Hollamby,M. J.; Shimizu, N.; Takagi, H.; Haruki, R.; Adachi, S.; Yagai, S. Sci. Adv. 2018, 4,eaat8466. |
| [29] | Foster,J. C.; Varlas, S.; Couturaud, B.; Coe, Z.; O'Reilly,R. K. J. Am. Chem. Soc. 2019, 141,2742-2753. |
| [30] | Manzano,J. I.; Cochet, F.; Boucherle, B.; Gomez-Perez, V.; Boumendjel, A.; Gamarro, F.; Peuchmaur, M. Eur. J. Med. Chem. 2016, 123,161. |
| [31] | Li, Z.; Zeng, Q.; Li, Z.; Dong, S.; Zhu, Z.; Li, Q.; Ye, C.; Di, C.; Liu, Y.; Qin, J. Macromolecules 2006, 39,8544. |
/
| 〈 |
|
〉 |
