Multicomponent Click Polymerization: A Facile Strategy toward Fused Heterocyclic Polymers

被引:59
作者
Deng, Haiqin [1 ,2 ,3 ]
Han, Ting [1 ,2 ,3 ]
Zhao, Engui [1 ,2 ,3 ]
Kwok, Ryan T. K. [1 ,2 ,3 ]
Lam, Jacky W. Y. [1 ,2 ,3 ]
Tang, Ben Zhong [1 ,2 ,3 ,4 ]
机构
[1] HKUST, Inst Adv Study, Inst Mol Funct Mat,Div Life Sci, Dept Chem,Div Biomed Engn,Hong Kong Branch,Chines, Kowloon, Hong Kong, Peoples R China
[2] HKUST, State Key Lab Mol Neurosci, Kowloon, Hong Kong, Peoples R China
[3] HKUST Shenzhen Res Inst, 9 Yuexing First RD,South Area,Hitech Pk, Shenzhen 518057, Peoples R China
[4] SCUT, Guangdong Innovat Res Team, SCUT HKUST Joint Res Lab, State Key Lab Luminescent Mat & Devices, Guangzhou 510640, Guangdong, Peoples R China
基金
美国国家科学基金会;
关键词
AGGREGATION-INDUCED EMISSION; SULFONYL AZIDE; ALKYNE; MACROMOLECULES; CYCLOADDITION; CHEMISTRY; DIYNES; DESIGN; ACIDS;
D O I
10.1021/acs.macromol.6b01217
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
We herein report a facile and efficient multi component click polymerization route to construct fused heterocyclic polymers with advanced functionalities. Mediated by CuI and trimethylamine at room temperature, diynes, disulfonyl azide, and salicylaldehyde, or o-hydroxylacetophenone undergo polymerizations efficiently and smoothly, affording high -molecular -weight poly(iminocoumarin)s (M-w up to 64 600) in satisfactory yields (up to 99%). This multicomponent click polymerization approach enjoys remarkable merits of both multicomponent reactions and click reactions, such as simple operation, high reaction efficiency and isolation yield, mild reaction conditions, and common substrates. The resulting polymers possess outstanding film-forming ability, high thermal stability, and good morphological stability. With tetraphenylethene luminogens embedded in the polymer chains, their solutions fluoresce weakly, whereas their aggregates emit intensely, demonstrative of a typical feature of aggregation-enhanced emission. Furthermore, the obtained polymers with bright film emission and high photosensitivity can be facilely fabricated into well-resolved 2D and 3D patterns by treatment of their films with UV light. Additionally, thanks to the highly polarized conjugated structures, the polymer films possess outstanding refractive indices (1.9284-1.7734) in the visible and near-IR regions (400-893 nm), which can be further adjusted by UV light.
引用
收藏
页码:5475 / 5483
页数:9
相关论文
共 47 条
[1]   Highly efficient one-pot synthesis of N-sulfonylamidines by Cu-catalyzed three-component coupling of sulfonyl azide, alkyne, and amine [J].
Bae, I ;
Han, H ;
Chang, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (07) :2038-2039
[2]  
Beyler CL., 2002, SFPE HDB FIRE PROTEC, V2
[3]  
Brandrup J., 2004, Polymer Handbook, V4
[4]   Fabrication of photonic crystals for the visible spectrum by holographic lithography [J].
Campbell, M ;
Sharp, DN ;
Harrison, MT ;
Denning, RG ;
Turberfield, AJ .
NATURE, 2000, 404 (6773) :53-56
[5]   Recent progress in organic photovoltaics: device architecture and optical design [J].
Cao, Weiran ;
Xue, Jiangeng .
ENERGY & ENVIRONMENTAL SCIENCE, 2014, 7 (07) :2123-2144
[6]   Construction of Functional Macromolecules with Well-Defined Structures by Indium-Catalyzed Three-Component Polycoupling of Alkynes, Aldehydes, and Amines [J].
Chan, Carrie Y. K. ;
Tseng, Nai-Wen ;
Lam, Jacky W. Y. ;
Liu, Jianzhao ;
Kwok, Ryan T. K. ;
Tang, Ben Zhong .
MACROMOLECULES, 2013, 46 (09) :3246-3256
[7]   Copper-catalyzed hydrative amide synthesis with terminal alkyne, sulfonyl azide, and water [J].
Cho, SH ;
Yoo, EJ ;
Bae, L ;
Chang, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (46) :16046-16047
[8]   Multicomponent reactions: advanced tools for sustainable organic synthesis [J].
Cioc, Razvan C. ;
Ruijter, Eelco ;
Orru, Romano V. A. .
GREEN CHEMISTRY, 2014, 16 (06) :2958-2975
[9]   Novel and efficient synthesis of iminocoumarins via copper-catalyzed multicomponent reaction [J].
Cui, Sun-Liang ;
Lin, Xu-Feng ;
Wang, Yan-Guang .
ORGANIC LETTERS, 2006, 8 (20) :4517-4520
[10]   Multifunctional Poly(N-sulfonylamidine)s Constructed by Cu-Catalyzed Three-Component Polycouplings of Diynes, Disulfonyl Azide, and Amino Esters [J].
Deng, Haiqin ;
Zhao, Engui ;
Li, Hongkun ;
Lam, Jacky W. Y. ;
Tang, Ben Zhong .
MACROMOLECULES, 2015, 48 (10) :3180-3189