Amplification of chirality in helical supramolecular columns

被引:29
作者
Brunsfeld, L [1 ]
Lohmeijer, BGG [1 ]
Vekemans, JAJM [1 ]
Meijer, EW [1 ]
机构
[1] Eindhoven Univ Technol, Lab Macromol & Organ Chem, NL-5600 MB Eindhoven, Netherlands
关键词
supramolecular chemistry; discotics; self-assembly; circular dichroism;
D O I
10.1023/A:1014417621324
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Strong amplification of chirality occurs in dynamic, but highly ordered, helical columns in n-butanol. for which one chiral seed molecule suffices to render a column of 400 molecules to become homochiral. The chiral columns are formed in a thermally dependent stepwise process. The transition from achiral stacks to helical columns is highly cooperative owing to well-defined intermolecular interactions. 'Sergeant and Soldiers' measurements allow for the calculation of the association constant and cooperativity length of the homochiral segments. The 'Sergeant and Soldiers' data on the number of molecules within a column show a strikingly good match with data obtained from a theoretical model describing the self-assembly of the discotic molecules as a function of temperature and concentration.
引用
收藏
页码:61 / 64
页数:4
相关论文
共 14 条
  • [1] Chiral autocatalysis:: where stereochemistry meets the origin of life
    Avalos, M
    Babiano, R
    Cintas, P
    Jiménez, JL
    Palacios, JC
    [J]. CHEMICAL COMMUNICATIONS, 2000, (11) : 887 - 892
  • [2] Chirality amplification in dynamic helical columns in water
    Brunsveld, L
    Lohmeijer, BGG
    Vekemans, JAJM
    Meijer, EW
    [J]. CHEMICAL COMMUNICATIONS, 2000, (23) : 2305 - 2306
  • [3] Hierarchical growth of chiral self-assembled structures in protic media
    Brunsveld, L
    Zhang, H
    Glasbeek, M
    Vekemans, JAJM
    Meijer, EW
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (26) : 6175 - 6182
  • [4] Chiral amplification in columns of self-assembled N,N′,N"-tris((S)-3,7-dimethyloctyl)benzene-1,3,5-tricarboxamide in dilute solution
    Brunsveld, L
    Schenning, APHJ
    Broeren, MAC
    Janssen, HM
    Vekemans, JAJM
    Meijer, EW
    [J]. CHEMISTRY LETTERS, 2000, (03) : 292 - 293
  • [5] Transfer of chiral information through molecular assembly
    Castellano, RK
    Nuckolls, C
    Rebek, J
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (48) : 11156 - 11163
  • [6] THE STEREOCHEMISTRY OF LINEAR MACROMOLECULES
    FARINA, M
    [J]. TOPICS IN STEREOCHEMISTRY, 1987, 17 : 1 - 111
  • [7] Feringa BL, 1999, ANGEW CHEM INT EDIT, V38, P3419
  • [8] A HELICAL POLYMER WITH A COOPERATIVE RESPONSE TO CHIRAL INFORMATION
    GREEN, MM
    PETERSON, NC
    SATO, T
    TERAMOTO, A
    COOK, R
    LIFSON, S
    [J]. SCIENCE, 1995, 268 (5219) : 1860 - 1866
  • [9] MACROMOLECULAR STEREOCHEMISTRY - THE OUT-OF-PROPORTION INFLUENCE OF OPTICALLY-ACTIVE CO-MONOMERS ON THE CONFORMATIONAL CHARACTERISTICS OF POLYISOCYANATES - THE SERGEANTS AND SOLDIERS EXPERIMENT
    GREEN, MM
    REIDY, MP
    JOHNSON, RJ
    DARLING, G
    OLEARY, DJ
    WILLSON, G
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (16) : 6452 - 6454
  • [10] Helical self-assembled polymers from cooperative stacking of hydrogen-bonded pairs
    Hirschberg, JHKK
    Brunsveld, L
    Ramzi, A
    Vekemans, JAJM
    Sijbesma, RP
    Meijer, EW
    [J]. NATURE, 2000, 407 (6801) : 167 - 170