Metal-Free Click Polymerization: Synthesis and Photonic Properties of Poly(aroyltriazole)s

被引:161
作者
Qin, Anjun [1 ,2 ]
Tang, Li [1 ]
Lam, Jacky W. Y. [2 ]
Jim, Cathy K. W. [2 ]
Yu, Yong [2 ]
Zhao, Hui [1 ]
Sun, Jingzhi [1 ]
Tang, Ben Zhong [1 ,2 ]
机构
[1] Zhejiang Univ, Key Lab Macromol Synth & Functionalizat, Minist Educ China, Dept Polymer Sci & Engn, Hangzhou 310027, Peoples R China
[2] Hong Kong Univ Sci & Technol, Dept Chem, Kowloon, Hong Kong, Peoples R China
基金
中国国家自然科学基金; 中国博士后科学基金;
关键词
AGGREGATION-INDUCED EMISSION; LIGHT-EMITTING-DIODES; REFRACTIVE-INDEX; CONTAINING POLYACETYLENES; ENHANCED EMISSIONS; OPTICAL-PROPERTIES; MATERIAL SCIENCE; FACILE SYNTHESIS; CHEMISTRY; PHOTOLUMINESCENCE;
D O I
10.1002/adfm.200801933
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Regioselective 1,3-dipolar polycycloadditions of tetraphenylethene (TPE)-containing diazides 1-3 and bis(aroylacetylene) 4 are initiated by simple heating, affording poly(aroyltriazole)s (PATAs) PI-PIII with high molecular weights in high yields. The PATAs are completely soluble in common organic solvents and stable at temperatures up to 358 degrees C. Thanks to their TPE units, the polymers show aggregation-induced emission and work as explosive sensors with high sensitivity. The PATAs are optically transparent in the whole visible spectral region. Their refractive indexes can be tuned to a great extent (Delta n approximate to 0.08) by simply changing their alkyl spacer lengths. The modified Abbe numbers of the PATAs are very high (up to 273), indicative of very low optical dispersions in the telecommunication-important wavelength region. UV irradiation through a photomask quenches the light emissions of the polymers, enabling the generation of two-dimensional fluorescent images without development. The polymers can be readily photo-crosslinked, yielding three-dimensional patterns with high resolutions.
引用
收藏
页码:1891 / 1900
页数:10
相关论文
共 89 条
[1]   Peptidomimetics via copper-catalyzed azide-alkyne cycloadditions [J].
Angell, Yu L. ;
Burgess, Kevin .
CHEMICAL SOCIETY REVIEWS, 2007, 36 (10) :1674-1689
[2]  
[Anonymous], 1984, 1 3 DIPOLAR CYCLOADD
[3]   1,3-dipolar cycloaddition for the generation of nanostructured semiconductors by heated probe tips [J].
Bakbak, Selma ;
Leech, Peter J. ;
Carson, Bradley E. ;
Saxena, Shubham ;
King, William P. ;
Bunz, Uwe H. F. .
MACROMOLECULES, 2006, 39 (20) :6793-6795
[4]   Emission enhancement by formation of aggregates in hybrid chromophoric surfactant amphiphile/silica nanocomposites [J].
Bhongale, CJ ;
Hsu, CS .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (09) :1404-1408
[5]   'Click' chemistry in polymer and material science: An update [J].
Binder, Wolfgang H. ;
Sachsenhofer, Robert .
MACROMOLECULAR RAPID COMMUNICATIONS, 2008, 29 (12-13) :952-981
[6]   Surface-modified nanoparticles via thermal and Cu(I)-mediated "click" chemistry:: Generation of luminescent CdSe nanoparticles with polar ligands guiding supramolecular recognition [J].
Binder, Wolfgang H. ;
Sachsenhofer, Robert ;
Straif, Christoph J. ;
Zirbs, Ronald .
JOURNAL OF MATERIALS CHEMISTRY, 2007, 17 (20) :2125-2132
[7]   Azide/alkyne-"click" reactions: Applications in material science and organic synthesis [J].
Binder, Wolfgang H. ;
Kluger, Christian .
CURRENT ORGANIC CHEMISTRY, 2006, 10 (14) :1791-1815
[8]   CuI-catalyzed alkyne-azide "click" cycloadditions from a mechanistic and synthetic perspective [J].
Bock, VD ;
Hiemstra, H ;
van Maarseveen, JH .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (01) :51-68
[9]   Modular synthesis and dynamics of a variety of donor-acceptor interlocked compounds prepared by click chemistry [J].
Braunschweig, Adam B. ;
Dichtel, William R. ;
Miljanic, Ognjen S. ;
Olson, Mark A. ;
Spruell, Jason M. ;
Khan, Saeed I. ;
Heath, James R. ;
Fraser Stoddart, J. .
CHEMISTRY-AN ASIAN JOURNAL, 2007, 2 (05) :634-647
[10]   Highly efficient organic light-emitting diodes with a silole-based compound [J].
Chen, HY ;
Lam, WY ;
Luo, JD ;
Ho, YL ;
Tang, BZ ;
Zhu, DB ;
Wong, M ;
Kwok, HS .
APPLIED PHYSICS LETTERS, 2002, 81 (04) :574-576