Synthesis and self-assembly of amphiphilic semifluorinated calix[4]arenes

被引:25
|
作者
Martin, OM
Mecozzi, S
机构
[1] Univ Wisconsin, Sch Pharm, Madison, WI 53705 USA
[2] Univ Wisconsin, Dept Chem, Madison, WI 53705 USA
关键词
calix[4]arenes; fluorophobic effect; fluorous phase; vesicles; stacked disks; self-assembly;
D O I
10.1080/10610270412331328998
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new amphiphilic molecule based on the calix[4]arene scaffold was synthesized by. appending perfluoroalkyl chains on the upper rim and polar groups on the lower rim of the macrocycle. This molecule self-assembles in water and methanol due to formation of a super-hydrophobic fluorous phase. Bilayer assemblies were observed using dynamic light scattering (131,S) and transmission electron microscopy (TEM). The aggregate architecture is strongly influenced by the solvent. Fibers formed by stacked disks were observed in methanol, whereas spherical aggregates were favored in an aqueous environment.
引用
收藏
页码:9 / 15
页数:7
相关论文
共 50 条
  • [1] Synthesis and pH-dependent self-assembly of semifluorinated calix[4]arenes
    Martin, Oana M.
    Mecozzi, Sandro
    TETRAHEDRON, 2007, 63 (25) : 5539 - 5547
  • [2] Self-assembly of amphiphilic calix[4]arenes in aqueous solution
    Strobel, M
    Kita-Tokarczyk, K
    Taubert, A
    Vebert, C
    Heiney, PA
    Chami, M
    Meier, W
    ADVANCED FUNCTIONAL MATERIALS, 2006, 16 (02) : 252 - 259
  • [3] Self-assembly of amphiphilic calix[4]arenes with liquid crystalline properties.
    Martin, OM
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 229 : U545 - U545
  • [4] The self-assembly of catenated calix[4]arenes
    Li, ZT
    Ji, GZ
    Yuan, SD
    Du, AL
    Ding, H
    Wei, M
    TETRAHEDRON LETTERS, 1998, 39 (36) : 6517 - 6520
  • [5] Solution self-assembly and solid state properties of fluorinated amphiphilic calix[4] arenes
    Martin, OM
    Yu, L
    Mecozzi, S
    CHEMICAL COMMUNICATIONS, 2005, (39) : 4964 - 4966
  • [6] Self-assembly of amphiphilic anionic calix[4]arenes and encapsulation of poorly soluble naproxen and flurbiprofen
    Barbera, Lucia
    Gattuso, Giuseppe
    Kohnke, Franz H.
    Notti, Anna
    Pappalardo, Sebastiano
    Parisi, Melchiorre F.
    Pisagatti, Ilenia
    Patane, Salvatore
    Micali, Norberto
    Villari, Valentina
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (23) : 6468 - 6473
  • [7] Functionalized calix[8]arenes, synthesis and self-assembly on graphite
    Zhang, H
    Podoprygorina, G
    Brusko, V
    Böhmer, V
    Janshoff, A
    CHEMISTRY OF MATERIALS, 2005, 17 (09) : 2290 - 2297
  • [8] Para-acyl calix[4]arenes:: amphiphilic self-assembly from the molecular to the mesoscopic level
    Shahgaldian, P
    Cesario, M
    Goreloff, P
    Coleman, AW
    CHEMICAL COMMUNICATIONS, 2002, (04) : 326 - 327
  • [9] Wide rim urethanes derived from calix[4]arenes:: Synthesis and self-assembly
    Cao, YD
    Vysotsky, MO
    Böhmer, V
    JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (09): : 3429 - 3434
  • [10] Amphiphilic Perylene-Calix[4]arene Hybrids: Synthesis and Tunable Self-Assembly
    Rodler, Fabian
    Schade, Boris
    Jaeger, Christof M.
    Backes, Susanne
    Hampel, Frank
    Boettcher, Christoph
    Clark, Timothy
    Hirsch, Andreas
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (09) : 3308 - 3317