Supramolecular daisy chains

被引:132
作者
Cantrill, SJ
Youn, GJ
Stoddart, JF
Williams, DJ
机构
[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
[2] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AY, England
关键词
D O I
10.1021/jo010405h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Two series of self-complementary daisy chain monomers, in which a secondary ammonium ion-containing arm is grafted onto a macrocycle with either a [24]- or [25]crown-8 constitution, have been synthesized. In the solid- and 'gas'-phases, the parent [24]crown-8-based monomer forms dimeric superstructures, as revealed by X-ray crystallography and mass spectrometry, respectively. Elucidation of the complicated solution-phase behavior of this compound was facilitated by the synthesis and study of both deuterated, and fluorinated, analogues. These investigations revealed that the cyclic dimeric superstructure also dominates in solution, except when extremes of either concentration (low), temperature (high), or solvent polarity (highly polar, e.g., dimethyl sulfoxide) are employed. Whereas, upon aggregation, the [24]crown-8-based daisy chain monomers have the capacity to form stereoisomeric superstructures further complicating the study of this series of compounds. The assembly of [25]crown-8-based monomers gives only achiral superstructures. The weaker association exhibited between secondary dialkylammonium ions and crown ethers with a [25]crown-8 constitution, however, resulted in limited oligomerization-only dimeric and trimeric superstructures were formed at experimentally attainable concentrations-of [25]crown-8-based daisy chain monomers.
引用
收藏
页码:6857 / 6872
页数:16
相关论文
共 146 条
  • [41] Axially coordinated porphyrins as new rotaxane stoppers
    Chichak, K
    Walsh, MC
    Branda, NR
    [J]. CHEMICAL COMMUNICATIONS, 2000, (10) : 847 - 848
  • [42] NEW ASPECTS OF CATIONIC POLYMERIZATION OF SPIROORTHOESTER - CATIONIC SINGLE RING-OPENING POLYMERIZATION AND EQUILIBRIUM POLYMERIZATION
    CHIKAOKA, S
    TAKATA, T
    ENDO, T
    [J]. MACROMOLECULES, 1991, 24 (25) : 6557 - 6562
  • [43] Self-assembly of hydrogen-bonded polymeric rods based on the cyanuric acid•melamine lattice
    Choi, IS
    Li, XH
    Simanek, EE
    Akaba, R
    Whitesides, GM
    [J]. CHEMISTRY OF MATERIALS, 1999, 11 (03) : 684 - 690
  • [44] Ciferri A, 2000, SUPRAMOLECULAR POLYMERS, P1
  • [45] Self-assembling capsules
    Conn, MM
    Rebek, J
    [J]. CHEMICAL REVIEWS, 1997, 97 (05) : 1647 - 1668
  • [46] Metallodendrimers: Metal ions as supramolecular glue
    Constable, EC
    [J]. CHEMICAL COMMUNICATIONS, 1997, (12) : 1073 - 1080
  • [47] Self-association without regard to prototropy. A heterocycle that forms extremely stable quadruply hydrogen-bonded dimers
    Corbin, PS
    Zimmerman, SC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (37) : 9710 - 9711
  • [48] The N-carbamoyl squaramide dimer:: a compact, strongly associated H-bonding motif
    Davis, AP
    Draper, SM
    Dunne, G
    Ashton, P
    [J]. CHEMICAL COMMUNICATIONS, 1999, (22) : 2265 - 2266
  • [49] USE OF HYDROGEN-BONDS TO CONTROL MOLECULAR AGGREGATION - EXTENSIVE, SELF-COMPLEMENTARY ARRAYS OF DONORS AND ACCEPTORS
    DUCHARME, Y
    WUEST, JD
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (24) : 5787 - 5789
  • [50] Quadruple hydrogen bonded oligo(p-phenylene vinylene) dimers
    El-ghayoury, A
    Peeters, E
    Schenning, APHJ
    Meijer, EW
    [J]. CHEMICAL COMMUNICATIONS, 2000, (19) : 1969 - 1970