特定序列两亲性偶氮苯交替类肽的自组装与光响应行为研究

朱熹萌; 张栋鑫; 刘帆; 武鹏超; 靳海宝; 林绍梁

doi:10.11777/j.issn1000-3304.2024.24156

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特定序列两亲性偶氮苯交替类肽的自组装与光响应行为研究

研究论文 | 更新时间：2025-01-26

- 特定序列两亲性偶氮苯交替类肽的自组装与光响应行为研究
- Self-assembly and Photo-responsive Behavior of Sequence-defined Amphiphilic Azobenzene Alternating Peptoids
- 高分子学报 2025年56卷第1期页码：104-113
- 作者机构：
  
  华东理工大学材料科学与工程学院上海市先进聚合物材料重点实验室上海 200237
- 作者简介：
  
  E-mail: haibaojin@ecust.edu.cn
  slin@ecust.edu.cn
- 基金信息：
  
  国家自然科学基金(基金号 ┣52373114;52325308);22001071,52073092┫
- DOI：10.11777/j.issn1000-3304.2024.24156
  中图分类号：
- CSTR：32057.14.GFZXB.2024.7275
- 纸质出版日期：2025-01-20，
  
  网络出版日期：2024-09-27，
  
  收稿日期：2024-06-05，
  
  录用日期：2024-08-19
- 稿件说明：
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朱熹萌, 张栋鑫, 刘帆, 武鹏超, 靳海宝, 林绍梁. 特定序列两亲性偶氮苯交替类肽的自组装与光响应行为研究. 高分子学报, 2025, 56(1), 104-113

Zhu X. M.; Zhang D. X.; Liu F.; Wu P. C.; Jin H. B.; Lin S. L. Self-assembly and photo-responsive behavior of sequence-defined amphiphilic azobenzene alternating peptoids. Acta Polymerica Sinica, 2025, 56(1), 104-113
朱熹萌, 张栋鑫, 刘帆, 武鹏超, 靳海宝, 林绍梁. 特定序列两亲性偶氮苯交替类肽的自组装与光响应行为研究. 高分子学报, 2025, 56(1), 104-113 DOI： 10.11777/j.issn1000-3304.2024.24156. CSTR： 32057.14.GFZXB.2024.7275.

Zhu X. M.; Zhang D. X.; Liu F.; Wu P. C.; Jin H. B.; Lin S. L. Self-assembly and photo-responsive behavior of sequence-defined amphiphilic azobenzene alternating peptoids. Acta Polymerica Sinica, 2025, 56(1), 104-113 DOI： 10.11777/j.issn1000-3304.2024.24156. CSTR： 32057.14.GFZXB.2024.7275.

摘要

刺激响应型序列可控聚合物在传感器、光电器件、信息存储、生物医药等领域中具有广阔的应用前景，因此其精准合成一直是一项极具挑战性的研究课题. 本工作通过固相亚单体合成法，设计并合成了一种新型特定序列结构、光响应的两亲性偶氮苯交替类肽，并通过溶液自组装制备了结构均匀的蠕虫状胶束. 利用耗散粒子动力学模拟，证实了侧链共轭堆积组装机理，及蠕虫状胶束内部两亲性偶氮苯交替类肽的排列方式. 在紫外光和可见光的交替照射下，聚集体能够实现从蠕虫状胶束到球形胶束的可逆光致结构转变. 本研究为刺激响应型序列可控聚合物的自组装研究提供了理论指导.

Abstract

Stimuli-responsive sequence-controlled polymers are capable of making reversible changes in physical and chemical property under external stimuli such as light

heat

electrical fields

and pH

exhibiting significant applications in the fields of sensing

optoelectronics

information storage

and biomedicines. However

the precise synthesis of stimuli-responsive sequence-controlled polymers remains a tremendous challenge. This study reported the design and synthesis of a photo-responsive and sequence-defined amphiphilic azobenzene alternating peptoids (AAAPs) of (NeAzo-

alt

-NEG

)

using the solid-phase sub-monomer synthesis technique. The self-assembly of (NeAzo-

alt

-NEG

)

in the aqueous solution formed uniform worm-like micelles. Dissipative particle dynamics simulations demonstrated the pendants conjugate packing mechanisms and the molecular stacking of AAAPs in the aggregates. The different stage of self-assembly was further confirmed by time-dependent transmission electron microscopy (TEM) characterizations. The self-assembly of AAAPs into uniform worm-like micelles was an active growth procedure from amorphous spherical micelles to crystalline worm-like micelles

with intermediate states of short nanorods. Additionally

the X-ray diffraction patterns further verified the high-crystalline architecture within the worm-like micelles. Ultraviolet-visible (UV-Vis) spectra in aqueous or THF solutions were recorded to unravel the photo-triggered conformation transition of azobenzene units. Under the alternating irradiation with ultraviolet and visible light

a reversible photo-triggered transformation from worm-like micelles to sphe

rical micelles with an average diameter of (67±12) nm was rendered owing to the photo-isomerization of azobenzene units. Our work provides valuable theoretical insights into the self-assembly of stimuli-responsive sequence-controlled polymers.

关键词

两亲性偶氮苯交替类肽固相合成自组装光响应性光致结构转变

Keywords

Amphiphilic azobenzene alternating peptoidsSolid-phase synthesisSelf-assemblyPhoto-responsive capacityPhoto-triggered structural transformation

references

Fong C.; Le T.; Drummond C. J.Lyotropic liquid crystal engineering-ordered nanostructured small molecule amphiphile self-assembly materials by design. Chem. Soc. Rev., 2012, 41(3), 1297-1322. doi:10.1039/c1cs15148ghttp://dx.doi.org/10.1039/c1cs15148g

Palermo V.; Samorì P.Molecular self-assembly across multiple length scales. Angew. Chem. Int. Ed., 2007, 46(24), 4428-4432. doi:10.1002/anie.200700416http://dx.doi.org/10.1002/anie.200700416

Lutz J. F.; Ouchi M.; Liu D. R.; Sawamoto M.Sequence-controlled polymers. Science, 2013, 341(6146), 1238149. doi:10.1126/science.1238149http://dx.doi.org/10.1126/science.1238149

张留乔, 黄智豪, 张正彪, 朱秀林.序列可控高分子的合成及应用. 高分子学报,. doi:10.11777/j.issn1000-3304.2018.18101http://dx.doi.org/10.11777/j.issn1000-3304.2018.18101

2018, (9), 1144-1154. doi:10.11777/j.issn1000-3304.2018.18101http://dx.doi.org/10.11777/j.issn1000-3304.2018.18101

Shi Q. Q.; Yin H.; Song R. D.; Xu J.; Tan J. J.; Zhou X.; Cen J.; Deng Z. Y.; Tong H. M.; Cui C. H.; Zhang Y. F.; Li X. P.; Zhang Z. B.; Liu S. Y.Digital micelles of encoded polymeric amphiphiles for direct sequence reading and ex vivo label-free quantification. Nat. Chem., 2023, 15(2), 257-270. doi:10.1038/s41557-022-01076-yhttp://dx.doi.org/10.1038/s41557-022-01076-y

Austin M. J.; Rosales A. M.Tunable biomaterials from synthetic, sequence-controlled polymers. Biomater. Sci., 2019, 7(2), 490-505. doi:10.1039/c8bm01215fhttp://dx.doi.org/10.1039/c8bm01215f

Zhang Z.; Xiong Y.; Yang P.; Li Y.; Tang R.; Nie X.; Chen G.; Wang L. H.; Hong C. Y.; You Y. Z.Easy access to diverse multiblock copolymers with on-demand blocks via thioester-relayed in-chain cascade copolymerization. Angew. Chem. Int. Ed, 2023, 62(15), e202216685. doi:10.1002/anie.202216685http://dx.doi.org/10.1002/anie.202216685

滕润鑫, 范震, 杜建忠. 肿瘤诊疗多肽/聚氨基酸自组装纳米材料. 高分子学报, 2023, 54(6), 853-869.

Shahrokhinia A.; Rijal S.; Sonmez Baghirzade B.; Scanga R. A.; Biswas P.; Tafazoli S.; Apul O. G.; Reuther J. F.Chain extensions in PhotoATRP-induced self-assembly (PhotoATR-PISA): a route to ultrahigh solids concentrations and click nanoparticle networks as adsorbents for water treatment. Macromolecules, 2022, 55(9), 3699-3710. doi:10.1021/acs.macromol.1c02636http://dx.doi.org/10.1021/acs.macromol.1c02636

Wang Y. X.; Zhang X. G.; Mu J.; Li C. X.Synthesis and pH/sugar/salt-sensitivity study of boronate crosslinked glycopolymer nanoparticles. New J. Chem., 2013, 37(3), 796-803. doi:10.1039/c2nj40998dhttp://dx.doi.org/10.1039/c2nj40998d

Vybornyi O.; Liu S. X.; Häner R.Stimuli-responsive supramolecular polymers from amphiphilic phosphodiester-linked azobenzene trimers. Angew. Chem. Int. Ed., 2021, 60(49), 25872-25877. doi:10.1002/anie.202108745http://dx.doi.org/10.1002/anie.202108745

Lv Y. S.; Wang L. Q.; Liu F.; Feng W. S.; Wei J.; Lin S. L.Self-assembly of amphiphilic alternating copolymers with stimuli-responsive rigid pendant groups. Polym. Chem., 2020, 11(29), 4798-4806. doi:10.1039/d0py00765jhttp://dx.doi.org/10.1039/d0py00765j

Li Y. M.; Liu S. Y.Enzyme-triggered transition from polymeric vesicles to core cross-linked micelles for selective release of antimicrobial agents. Anal. Chim. Acta, 2017, 1(7), 1178-1190. doi:10.11777/j.issn1000-3304.2017.17035http://dx.doi.org/10.11777/j.issn1000-3304.2017.17035

Jiang C. Q.; Xu G. H.; Gao J. P.Stimuli-responsive macromolecular self-assembly. Sustainability, 2022, 14(18), 11738. doi:10.3390/su141811738http://dx.doi.org/10.3390/su141811738

Islam M. R.; Lu Z. Z.; Li X.; Sarker A. K.; Hu L.; Choi P.; Li X.; Hakobyan N.; Serpe M. J.Responsive polymers for analytical applications: a review. Anal. Chim. Acta, 2013, 789, 17-32. doi:10.1016/j.aca.2013.05.009http://dx.doi.org/10.1016/j.aca.2013.05.009

Wang Y.; Feng A.; Yuan J.Application of stimuli-responsive polymer in catalyst systems of gold nanoparticles. Prog. Chem., 2016, 28(7), 1054-1061.

Xiong R. H.; Xu R. X.; Huang C. B.; De Smedt S.; Braeckmans K.Stimuli-responsive nanobubbles for biomedical applications. Chem. Soc. Rev., 2021, 50(9), 5746-5776. doi:10.1039/c9cs00839jhttp://dx.doi.org/10.1039/c9cs00839j

Yuan Y.; Nie T. Q.; Fang Y. F.; You X. R.; Huang H.; Wu J.Stimuli-responsive cyclodextrin-based supramolecular assemblies as drug carriers. J. Mater. Chem. B, 2022, 10(13), 2077-2096. doi:10.1039/d1tb02683fhttp://dx.doi.org/10.1039/d1tb02683f

Zhang X. H.; Cheng D. B.; Ji L.; An H. W.; Wang D.; Yang Z. X.; Chen H.; Qiao Z. Y.; Wang H.Photothermal-promoted morphology transformation in vivo monitored by photoacoustic imaging. Nano Lett., 2020, 20(2), 1286-1295. doi:10.1021/acs.nanolett.9b04752http://dx.doi.org/10.1021/acs.nanolett.9b04752

Zuckermann, R. N. Peptoid origins. Pept. Sci., 2011, 96(5), 545-555. doi:10.1002/bip.21573http://dx.doi.org/10.1002/bip.21573

Sun J.; Zuckermann R. N.Peptoid polymers: a highly designable bioinspired material. ACS Nano, 2013, 7(6), 4715-4732. doi:10.1021/nn4015714http://dx.doi.org/10.1021/nn4015714

Zuckermann R. N.; Kerr J. M.; Kent S. B. H.; Moos W. H.Efficient method for the preparation of peptoids[oligo(N-substituted glycines)] by submonomer solid-phase synthesis. J. Am. Chem. Soc., 1992, 114(26), 10646-10647. doi:10.1021/ja00052a076http://dx.doi.org/10.1021/ja00052a076

Liu J. L.; Cai B.; Cui L. F.; Chen C. L.Peptoid-based hierarchically-structured biomimetic nanomaterials: synthesis, characterization and applications. Sci. China Mater., 2020, 63(7), 1099-1112. doi:10.1007/s40843-020-1296-8http://dx.doi.org/10.1007/s40843-020-1296-8

Knight A. S.; Zhou E. Y.; Francis M. B.; Zuckermann R. N.Sequence programmable peptoid polymers for diverse materials applications. Adv. Mater., 2015, 27(38), 5665-5691. doi:10.1002/adma.201500275http://dx.doi.org/10.1002/adma.201500275

Robertson E. J.; Battigelli A.; Proulx C.; Mannige R. V.; Haxton T. K.; Yun L. S.; Whitelam S.; Zuckermann R. N.Design, synthesis, assembly, and engineering of peptoid nanosheets. Acc. Chem. Res., 2016, 49(3), 379-389. doi:10.1021/acs.accounts.5b00439http://dx.doi.org/10.1021/acs.accounts.5b00439

Jin H. B.; Ding Y. H.; Wang M. M.; Song Y.; Liao Z. H.; Newcomb C. J.; Wu X. P.; Tang X. Q.; Li Z.; Lin Y. H.; Yan F.; Jian T. Y.; Mu P.; Chen C. L.Designable and dynamic single-walled stiff nanotubes assembled from sequence-defined peptoids. Nat. Commun., 2018, 9(1), 270. doi:10.1038/s41467-017-02059-1http://dx.doi.org/10.1038/s41467-017-02059-1

Sun J.; Jiang X.; Lund R.; Downing K. H.; Balsara N. P.; Zuckermann R. N.Self-assembly of crystalline nanotubes from monodisperse amphiphilic diblock copolypeptoid tiles. Proc. Natl. Acad. Sci. USA, 2016, 113(15), 3954-3959. doi:10.1073/pnas.1517169113http://dx.doi.org/10.1073/pnas.1517169113

Peng G. P.; Jin H. B.; Liu F.; Yang X. Y.; Sui P. L.; Lin S. L.Biomimetic ultrathin pepsomes for photo-controllable catalysis. Sci. China Chem., 2022, 65(12), 2444-2449. doi:10.1007/s11426-022-1353-4http://dx.doi.org/10.1007/s11426-022-1353-4

Wu P. C.; Sui P. L.; Peng G. P.; Sun Z. C.; Liu F.; Yao W. Q.; Jin H. B.; Lin S. L.Designable photo-responsive micron-scale ultrathin peptoid nanobelts for enhanced performance on hydrogen evolution reaction. Adv. Mater., 2024, 36(16), 2312724. doi:10.1002/adma.202312724http://dx.doi.org/10.1002/adma.202312724

Gohy J. F.; Zhao Y.Photo-responsive block copolymer micelles: design and behavior. Chem. Soc. Rev., 2013, 42(17), 7117-7129. doi:10.1039/c3cs35469ehttp://dx.doi.org/10.1039/c3cs35469e

Qian J.; Zhang L. Z.; Wang Z. H.; Wu S. J.; Jiang X. S.; Lin S. L.; Yao Y.Multiple regulation of dynamic wrinkles based on conjugated copolymer network. Sci. China Mater., 2024, 67(1), 363-371. doi:10.1007/s40843-023-2684-3http://dx.doi.org/10.1007/s40843-023-2684-3

Tamesue S.; Takashima Y.; Yamaguchi H.; Shinkai S.; Harada A.Photoswitchable supramolecular hydrogels formed by cyclodextrins and azobenzene polymers. Angew. Chem. Int. Ed, 2010, 49(41), 7461-7464. doi:10.1002/anie.201003567http://dx.doi.org/10.1002/anie.201003567

Zhao Y. L.; Tao X. F.; Xu B. B.; Liu W. B.; Lin S. L.Robust thiazole-linked covalent organic frameworks with post-modified azobenzene groups: photo-regulated dye adsorption and separation. Adv. Funct. Mater., 2024, 34(34), 2401895. doi:10.1002/adfm.202401895http://dx.doi.org/10.1002/adfm.202401895

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