High-Generation Second-Order Nonlinear Optical (NLO) Dendrimers that Contain Isolation Chromophores: Convenient Synthesis by Using Click Chemistry and their Increased NLO Effects

被引:59
作者
Wu, Wenbo [2 ]
Li, Conggang [1 ]
Yu, Gui [3 ]
Liu, Yunqi [3 ]
Ye, Cheng [3 ]
Qin, Jingui [2 ]
Li, Zhen [2 ]
机构
[1] Chinese Acad Sci, China State Key Lab Magnet Resonance & Atom & Mol, Wuhan Inst Phys & Math, Wuhan 430071, Peoples R China
[2] Wuhan Univ, Dept Chem, Hubei Key Lab Organ & Polymer Optoelect Mat, Wuhan 430072, Peoples R China
[3] Chinese Acad Sci, Organ Solids Labs, Inst Chem, Beijing 100080, Peoples R China
基金
美国国家科学基金会;
关键词
azo compounds; chromophores; click chemistry; dendrimers; nonlinear optics; ORGANIC ELECTROOPTIC MATERIALS; MAIN-CHAIN POLYURETHANES; THERMAL-STABILITY; POLYMERS; DESIGN; MACROMOLECULES; EFFICIENT; ASSEMBLIES; MOIETIES; LAYER;
D O I
10.1002/chem.201200441
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Herein, high-generation dendrimers G4-NS and G5-NS, which contained 30 and 62 azo-benzene chromophore moieties, respectively, were conveniently prepared in high purity and satisfied yields by a combination of divergent and convergent approaches, coupled with the utilization of the powerful Sharpless click reaction. These dendrimers possessed a regular structure of alternating layers of nitro-based and sulfonyl-based azo chromophores in which the sulfonyl-based azo-chromophore moieties were utilized as co-isolation groups for the nitro-based moieties to achieve larger macroscopic second-order nonlinear optical (NLO) effects. These high-generation dendrimers (G4-NS and G5-NS) displayed very large NLO efficiencies (up to 253.0 pm?V-1), which is, to the best of our knowledge, the record highest efficiency for simple azo-chromophore moieties.
引用
收藏
页码:11019 / 11028
页数:10
相关论文
共 61 条
[31]   Tailored Organic Electro-optic Materials and Their Hybrid Systems for Device Applications [J].
Luo, Jingdong ;
Huang, Su ;
Shi, Zhengwei ;
Polishak, Brent M. ;
Zhou, Xing-Hua ;
Jen, Alex K-Y. .
CHEMISTRY OF MATERIALS, 2011, 23 (03) :544-553
[32]   Rational molecular design and supramolecular assembly of highly efficient organic electro-optic materials [J].
Luo, Jingdong ;
Zhou, Xing-Hua ;
Jen, Alex K. -Y. .
JOURNAL OF MATERIALS CHEMISTRY, 2009, 19 (40) :7410-7424
[33]  
Ma H, 2002, ADV FUNCT MATER, V12, P565, DOI 10.1002/1616-3028(20020916)12:9<565::AID-ADFM565>3.0.CO
[34]  
2-8
[35]   Design and synthesis of chromophores and polymers for electro-optic and photorefractive applications [J].
Marder, SR ;
Kippelen, B ;
Jen, AKY ;
Peyghambarian, N .
NATURE, 1997, 388 (6645) :845-851
[36]  
MARKS TJ, 1995, ANGEW CHEM INT EDIT, V34, P155, DOI 10.1002/anie.199501551
[37]  
MARKS TJ, 1995, ANGEW CHEM, V107, P167
[38]   Wideband 15 THz response using organic electro-optic polymer emitter-sensor pairs at telecommunication wavelengths [J].
McLaughlin, Colin V. ;
Hayden, L. Michael ;
Polishak, Brent ;
Huang, Su ;
Luo, Jingdong ;
Kim, Tae-Dong ;
Jen, Alex K. -Y. .
APPLIED PHYSICS LETTERS, 2008, 92 (15)
[39]   N-acetylgalactosamine-functionalized dendrimers as hepatic cancer cell-targeted carriers [J].
Medina, Scott H. ;
Tekumalla, Venkatesh ;
Chevliakov, Maxim V. ;
Shewach, Donna S. ;
Ensminger, William D. ;
El-Sayed, Mohamed E. H. .
BIOMATERIALS, 2011, 32 (17) :4118-4129
[40]   Cu-catalyzed azide-alkyne cycloaddition [J].
Meldal, Morten ;
Tornoe, Christian Wenzel .
CHEMICAL REVIEWS, 2008, 108 (08) :2952-3015