Formation of trimethylsilylated open-cage oligomeric azidophenylsilsesquioxanes

被引:28
作者
Ervithayasuporn, Vuthichai [1 ,2 ]
Wang, Xin [2 ]
Gacal, Burcin [3 ]
Gacal, Bahadir N. [3 ]
Yagci, Yusuf [3 ]
Kawakami, Yusuke [2 ]
机构
[1] Mahidol Univ, Dept Chem, Fac Sci, Bangkok 10400, Thailand
[2] Japan Adv Inst Sci & Technol JAIST, Sch Mat Sci, Nomi, Ishikawa 9231292, Japan
[3] Istanbul Tech Univ, Dept Chem, TR-34469 Istanbul, Turkey
关键词
Silsesquioxane; Oligomer; Azide; Trimethylsilyl group; Open-cage structure; CLICK CHEMISTRY; SILSESQUIOXANE; POSS; AZIDES;
D O I
10.1016/j.jorganchem.2010.11.030
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Formation of open-cage oligomeric azidophenylsilsesquioxane was surprisingly discovered in the successive reduction and azidation reactions starting from octa(nitrophenyl)octasilsesquioxane. The mixture of oligomeric products was characterized after end-capping with trimethylsilyl groups. The IR spectra confirmed the introduction of azide function to aromatic moiety, and trimethylsilyl group on silsesquioxane framework. Together with the GPC result, NMR analysis revealed the introduction of different number of trimethylsilyl groups in the structure. Some of them maintained the cage-like silsesquioxane structure characterized by XRD analysis. Their TGA profiles gave a unique pattern with clear two-step mass loss with the first mass loss of about 8-10 wt% from 180 to 225 degrees C corresponding to a thermal decomposition of azide groups. (C) 2010 Elsevier B.V. All rights reserved.
引用
收藏
页码:2193 / 2198
页数:6
相关论文
共 38 条
[1]  
AC, 2008, Pharm Res, V25, P2216
[2]   Enhancing electrochromic properties of polypyrrole by silsesquioxane nanocages [J].
Ak, Metin ;
Gacal, Burcin ;
Kiskan, Baris ;
Yagci, Yusuf ;
Toppare, Levent .
POLYMER, 2008, 49 (09) :2202-2210
[3]   Efficient conversion of aromatic amines into azides: A one-pot synthesis of triazole linkages [J].
Barral, Karine ;
Moorhouse, Adam D. ;
Moses, John E. .
ORGANIC LETTERS, 2007, 9 (09) :1809-1811
[4]   Fluoride-ion encapsulation within a silsesquioxane cage [J].
Bassindale, AR ;
Pourny, M ;
Taylor, PG ;
Hursthouse, MB ;
Light, ME .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (30) :3488-3490
[5]   PREPARATION + CHARACTERIZATION OF LOWER EQUILIBRATED PHENYLSILSESQUIOXANES [J].
BROWN, JF ;
VOGT, LH ;
PRESCOTT, PI .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (06) :1120-&
[6]   Organic/inorganic imide nanocomposites from aminophenylsilsesquioxanes [J].
Choi, JW ;
Tamaki, R ;
Kim, SG ;
Laine, RM .
CHEMISTRY OF MATERIALS, 2003, 15 (17) :3365-3375
[7]   Recent Developments in the Chemistry of Cubic Polyhedral Oligosilsesquioxanes [J].
Cordes, David B. ;
Lickiss, Paul D. ;
Rataboul, Franck .
CHEMICAL REVIEWS, 2010, 110 (04) :2081-2173
[8]  
Erben C., 2006, SILICON CHEM, DOI DOI 10.1007/S11201-005-9000-5
[9]   Synthesis, characterization, and OLED application of oligo(p-phenylene ethynylene)s with polyhedral oligomeric silsesquioxanes (POSS) as pendant groups [J].
Ervithayasuporn, Vuthichai ;
Abe, Junichi ;
Wang, Xin ;
Matsushima, Toshinori ;
Murata, Hideyuki ;
Kawakami, Yusuke .
TETRAHEDRON, 2010, 66 (48) :9348-9355
[10]   Synthesis and characterization of highly pure azido-functionalized polyhedral oligomeric silsesquioxanes (POSS) [J].
Ervithayasuporn, Vuthichai ;
Wang, Xin ;
Kawakami, Yusuke .
CHEMICAL COMMUNICATIONS, 2009, (34) :5130-5132