Synthesis and Photo-responsive Self-Assembly of Azobenzene-Containing Molecular Brushes

doi:10.6023/cjoc202102047

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (7): 2891-2897.DOI: 10.6023/cjoc202102047 Previous Articles Next Articles

NOTES

含偶氮苯侧链分子刷聚合物的合成及其光响应自组装

钱鸿宇, 何品, 张璐, 陈珂, 徐彬彬, 林绍梁^*()

华东理工大学材料科学与工程学院上海 200237

收稿日期:2021-02-25 修回日期:2021-03-25 发布日期:2021-04-29
通讯作者: 林绍梁
基金资助:
国家自然科学基金(52073092); 国家自然科学基金(51873061); 国家自然科学基金(22001072)

Synthesis and Photo-responsive Self-Assembly of Azobenzene-Containing Molecular Brushes

Hongyu Qian, Pin He, Lu Zhang, Ke Chen, Binbin Xu, Shaoliang Lin()

School of Materials Science and Engineering, East China University of Science and Technology, Shanghai 200237

Received:2021-02-25 Revised:2021-03-25 Published:2021-04-29
Contact: Shaoliang Lin
Supported by:
National Natural Science Foundation of China(52073092); National Natural Science Foundation of China(51873061); National Natural Science Foundation of China(22001072)

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Abstract

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.

Key words: azobenzene, molecular brushes, photo-responsiveness, supramolecular self-assembly

Cite this article

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.

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Fig. & Tab. 6

Scheme 1. (A) Syntheses of poly(Br-acrylate-alkyne) (1), and (B) PA-g-PAzo/Bar (4)

Figure 1. (A)1H NMR spectrum and (B) GPC trace of PA-g-PAzo/Bar (4) of PA-g-PAzo/Bar (4)

Figure 2. UV-Vis absorption spectra of PA-g-PAzo/Bar micelle solution (0.2 mg•mL–1, CHCl3/MCH, V∶V=1∶0.2) (A) Upon irradiation of 365 nm light; (B) upon irradiation of 450 nm light

Figure 3. TEM images of PA-g-PAzo/Bar micelle solution: (A, B) 0.2 mg•mL–1 micelle solution, (C) 0.2 mg•mL–1 micelle solution after storing 7 d, and (D) 1 mg•mL–1 micelle solution; (E) Schematic illustration of the obtained cylinder and compound micelles

Figure 4. (A), (B) TEM images of PA-g-PAzo/Bar cylinder micelles after UV irradiation. (C) Simplified schematic illustration of the obtained porous nanosheet after UV irradiation

Figure 5. TEM images of PA-g-PAzo/Bar compound micelles after UV irradiation (A, B) 1 h, and (C, D) 3 h

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含偶氮苯侧链分子刷聚合物的合成及其光响应自组装

Synthesis and Photo-responsive Self-Assembly of Azobenzene-Containing Molecular Brushes

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