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Synthesis and Self-assembly of Azobenzene-Functionalized Polypeptoids Based on Ugi Multicomponent Polymerization
Research Article | 更新时间：2026-05-11
|
Synthesis and Self-assembly of Azobenzene-Functionalized Polypeptoids Based on Ugi Multicomponent Polymerization
增强出版- Acta Polymerica Sinica Vol. 56, Issue 10, Pages: 1716-1726(2025)
- 作者机构：
上海市先进聚合物材料重点实验室 华东理工大学材料科学与工程学院 上海 200237
- 作者简介：
Xin-feng Tao, E-mail: taoxinfeng@ecust.edu.cn
Shao-liang Lin, E-mail: slin@ecust.edu.cn
- 基金信息：
DOI：10.11777/j.issn1000-3304.2025.25100
CLC：- CSTR：32057.14.GFZXB.2025.7420
Received：14 April 2025，
Accepted：17 May 2025，
Online First：24 July 2025，
Published：20 October 2025
- 稿件说明：
移动端阅览
李妙川, 金圣, 冯伟胜, 陶鑫峰, 林绍梁. 基于Ugi多组分聚合的偶氮苯聚类肽合成与自组装. 高分子学报, 2025, 56(10), 1716-1726
Li, M. C.; Jin, S.; Feng, W. S.; Tao, X. F.; Lin, S. L. Synthesis and self-assembly of azobenzene-functionalized polypeptoids based on Ugi multicomponent polymerization. Acta Polymerica Sinica, 2025, 56(10), 1716-1726
李妙川, 金圣, 冯伟胜, 陶鑫峰, 林绍梁. 基于Ugi多组分聚合的偶氮苯聚类肽合成与自组装. 高分子学报, 2025, 56(10), 1716-1726 DOI： 10.11777/j.issn1000-3304.2025.25100. CSTR： 32057.14.GFZXB.2025.7420.
Li, M. C.; Jin, S.; Feng, W. S.; Tao, X. F.; Lin, S. L. Synthesis and self-assembly of azobenzene-functionalized polypeptoids based on Ugi multicomponent polymerization. Acta Polymerica Sinica, 2025, 56(10), 1716-1726 DOI： 10.11777/j.issn1000-3304.2025.25100. CSTR： 32057.14.GFZXB.2025.7420.
Synthesis and Self-assembly of Azobenzene-Functionalized Polypeptoids Based on Ugi Multicomponent Polymerization 增强出版
摘要
设计合成了4-异氰基偶氮苯(Azo-NC)单体和4-((2
5
8
11-四氧杂十三烷-13-基)氧基)苯甲醛(EG
4
-CHO)单体，并以4-氨基丁酸(AA
4
)、5-氨基戊酸(AA
5
)、6-氨基己酸(AA
6
)为氨基酸单体，通过Ugi多组分聚合成功制备了新型主链结构的偶氮苯功能化聚(
γ
-类肽)、聚(
δ
-类肽)和聚(
ε
-类肽)，即P(AA
x
-Azo/EG
4
) (
x
=4、5和6). 通过核磁共振氢谱(
1
H-NMR)、红外光谱(FTIR)和体积排除色谱(SEC)表征了偶氮苯聚类肽的化学结构、分子量和分子量分布. 系统研究了P(AA
x
-Azo/EG
4
)的自组装行为，利用透射电子显微镜(TEM)对组装体的形貌进行了详细表征，获得了“松针”状和“竹叶”状等形貌的组装体. 紫外-可见光谱(UV-Vis)测试表明，随着氨基酸重复单元长度的增加，组装体中偶氮苯基团从H-型排列向J-型排列转变，且光致异构化速率加快. P(AA
x
-Azo/EG
4
)组装体具有良好的光响应性和温度响应性，“竹叶”形片状组装体在365 nm紫外光照后转变为纺锤形聚集体，在45 ℃热处理后转变为球形大复合胶束.
Abstract
Azobenzene-functionalized polypeptoids represent a significant class of photo-responsive smart materials
exhibiting remarkable application potential in biomimetics
medicine
and other fields because of their excellent biocompatibility
remotely controllable structure
and non-contact variable performance. However
reported azobenzene-functionalized polypeptoids are mainly poly(
α
-peptoid) synthesized by solid-phase synthesis and ring-opening polymerization of
N
-substituted glycine
N
-carboxyanhydride (NNCA) or
N
-substituted glycine
N
-thiocarboxyanhydride (NNTA). Azobenzene-functionalized polypeptoids with alternative main-chain structures have rarely been explored. In this study
novel azobenzene-functionalized polypeptoids were synthesized through Ugi multicomponent polymerization. First
4-isocyanoazobenzene (Azo-NC) and 4-((2
5
8
11-tetraoxatridecan-13-yl)oxy)benzaldehyde (EG
4
-CHO) were designed and synthesized
which could endow polypeptoids with photo-responsiveness and thermo-responsiveness. Azo-NC and EG
4
-CHO were polymerized with 4-aminobutyric acid (AA
4
)
5-aminovaleric acid (AA
5
)
and 6-aminocaproic acid (AA
6
) respectively in trifluoroethanol at 50 ℃ for 96 h
yielding azobenzene-functionalized poly(
γ
-peptoid) (P(AA
4
-Azo/EG
4
))
poly(
δ
-peptoid) (P(AA
5
-Azo/EG
4
))
and poly(
ε
-peptoid) (P(AA
6
-Azo/EG
4
)) with high yields (
>
86%). The chemical structures
molecular weights (MWs)
and MW distributions of P(AA
x
-Azo/EG
4
) were confirmed using proton nuclear magnetic resonance (
1
H-NMR) spectroscopy
Fourier transform infrared (FTIR) spectroscopy
and size-exclusion chromatography (SEC). The self-assembly behavior of P(AA
x
-Azo/EG
4
) in an aqueous solution was systematically investigated
and the resulting morphologies were characterized by TEM. At an initial water At an initial water content of 33% in volume
P(AA
4
-Azo/EG
4
) formed "pine leaf"-like assemblies
whereas P(AA
5
-Azo/EG
4
) and P(AA
6
-Azo/EG
4
) formed "bamboo leaf"-like assemblies
which indicated that aspect ratio of the assemblies decreased with increasing lengths of the amino acid repeat unit. As the initial water content was increased
spherical composite micelles gradually appeared. UV-Vis spectroscopy measurements revealed that P(AA
x
-Azo/EG
4
) and its assemblies showed excellent photo-isomerization properties. Notably
with longer amino acid repeat units
the azobenzene groups within the assemblies changed from an H-type to a J-type arrangement
accompanied by an accelerated rate of photo-induced
trans
-to-
cis
isomerization. The P(AA
x
-Azo/EG
4
) assemblies exhibited excellent photo-responsiveness and thermo-responsiveness. Specifically
the "bamboo leaf"-like assemblies of P(AA
6
-Azo/EG
4
) transformed into spindle-shaped aggregates after 6 h irradiation of 365 nm ultraviolet light. The "bamboo leaf"-like assemblies of P(AA
5
-Azo/EG
4
) reorganized into spherical composite micelles after 4 h heat treatment at 45 ℃.
关键词
Keywords
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