MOLECULAR DESIGN AND CHARACTERIZATIONS OF NEW CALIXARENE-BASED GELATORS OF ORGANIC FLUIDS

被引:77
作者
AOKI, M [1 ]
NAKASHIMA, K [1 ]
KAWABATA, H [1 ]
TSUTSUI, S [1 ]
SHINKAI, S [1 ]
机构
[1] RES DEV CORP JAPAN,ERATO,CHEMIRECOGN PROJECT,332-1 KAMIKOGA,CHIKUSHINO,FUKUOKA 818,JAPAN
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 1993年 / 03期
关键词
D O I
10.1039/p29930000347
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We have found that certain calix[n]arenes having long acyl groups at the p-positions (e.g., 5,11,17,23,29,35,41,47-octadodecanoylcalix[8]arene-49,50,51,52,53,54,55,56-octol: 2C-8(12)) act as excellent and unique gelators of various organic solvents (e.g., toluene, carbon tetrachloride, carbon disulfide, hexane, isopropanol, etc.). The sol-gel phase transition temperatures (T(gel)), could be determined by the inverted test-tube method or by the DSC method. The change in the aggregation mode at the phase transition temperature was directly observable by an optical microscope: below T(gel) the fibrillar network (diameter ca. 1 mum) appeared whereas above T(gel) it 'melted' down. It was shown on the basis of these measurements that the sol-gel phase transition occurs reversibly. The spectroscopic studies using H-1 NMR and IR spectroscopy and the comparative experiments using the analogues of 2C-8(12) (nine cyclic and six non-cyclic) established that the prerequisites for the formation of the stable organic gels are (i) the intermolecular C=O ... HO hygrogen-bonding interaction to form the three-dimensional network and (ii) the moderate affinity of gelators with solvent molecules. The results offer important strategies useful for the molecular design of new gelators of organic fluids.
引用
收藏
页码:347 / 354
页数:8
相关论文
共 29 条
  • [1] CALIXARENE-BASED GELATORS OF ORGANIC FLUIDS
    AOKI, M
    MURATA, K
    SHINKAI, S
    [J]. CHEMISTRY LETTERS, 1991, (10) : 1715 - 1718
  • [2] PKA OF CALIXARENES AND ANALOGS IN NONAQUEOUS SOLVENTS
    ARAKI, K
    IWAMOTO, K
    SHINKAI, S
    MATSUDA, T
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1990, 63 (12) : 3480 - 3485
  • [3] FRIES REARRANGEMENT IN CALIXARENE ESTERS - A NEW ENTRY FOR THE SYNTHESIS OF PARA-SUBSTITUTED CALIXARENES
    ARIMURA, T
    SHINKAI, S
    MATSUDA, T
    HIRATA, Y
    SATOH, H
    MANABE, O
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1988, 61 (10) : 3733 - 3734
  • [4] PREPARATION OF SERIES OF CALIX[6]ARENES AND CALIX[8]ARENES DERIVED FROM P-N-ALKYLPHENOLS
    ASFARI, Z
    VICENS, J
    [J]. TETRAHEDRON LETTERS, 1988, 29 (22) : 2659 - 2660
  • [5] A NOVEL SMALL MOLECULAR LUMINESCENT GELLING AGENT FOR ALCOHOLS
    BROTIN, T
    UTERMOHLEN, R
    FAGES, F
    BOUASLAURENT, H
    DESVERGNE, JP
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (06) : 416 - 418
  • [6] George B., 1987, INFRARED SPECTROSCOP
  • [7] TOPICS IN CALIXARENE CHEMISTRY
    GUTSCHE, CD
    ALAM, I
    IQBAL, M
    MANGIAFICO, T
    NAM, KC
    ROGERS, J
    SEE, KA
    [J]. JOURNAL OF INCLUSION PHENOMENA, 1989, 7 (01): : 61 - 72
  • [8] CALIXARENES .13. THE CONFORMATIONAL PROPERTIES OF CALIX[4]ARENES, CALIX[6]ARENES, CALIX[8]ARENES, AND OXACALIXARENES
    GUTSCHE, CD
    BAUER, LJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (21) : 6052 - 6059
  • [9] CALIXARENES
    GUTSCHE, CD
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 1983, 16 (05) : 161 - 170
  • [10] CALIXARENES .12. THE SYNTHESIS OF FUNCTIONALIZED CALIXARENES
    GUTSCHE, CD
    LIN, LG
    [J]. TETRAHEDRON, 1986, 42 (06) : 1633 - 1640