Amphiphilic N-benzoyl-1-amino-1-deoxy-D-glucitol derivatives forming thermotropic lamellar, columnar and different types of cubic mesophases

被引:101
作者
Borisch, K
Diele, S
Goring, P
Muller, H
Tschierske, C
机构
[1] UNIV HALLE WITTENBERG,INST ORGAN CHEM,D-06120 HALLE,GERMANY
[2] UNIV HALLE WITTENBERG,INST PHYS CHEM,D-06108 HALLE,GERMANY
关键词
D O I
10.1080/026782997209144
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Novel amphiphilic glucamine derivatives have been synthesized. These are N-benzoyl-1-deoxyl-methylamino-D-glucitols and N-benzoyl-1-amino-1-deoxy-D-glucitols carrying one, two or three aliphatic chains (CnH2n+1O- with n = 3, 6 and 12) grafted to the benzamido group. The thermotropic mesophases of these compounds were studied by thermal polarizing optical microscopy and differential scanning calorimetry, and some also by X-ray scattering. Depending on the number and the length of the alkyl chains lamellar, bicontinuous cubic, hexagonal columnar or inverted micellar cubic mesophases were detected by analogy with lyotropic systems. In the contact region between lamellar phases of the single chain amphiphiles and micellar cubic phases of the mesomorphic triple chain compounds, hexagonal columnar phases can be induced. A hexagonal columnar phase was also induced in the contact region between a bicontinuous and a micellar cubic mesophase. The lyotropic liquid crystalline behaviour of the dodecyloxy substituted N-benzoyl-1-deoxy-1-methylamino-D-glucitols was investigated by the solvent penetration method using ethylene glycol as protic solvent. On increasing the solvent content, the double chain compound forms a cubic and a lamellar mesophase and the triple chain compound forms a hexagonal columnar lyomesophase. The dodecyloxy substituted compounds were also investigated with respect to their behaviour as thin films at the air-water interface using a Langmuir film-balance. Different types of pi/A-isotherms were observed whereby the molecular areas at collapse were determined either by the size of the carbohydrate head group (single chain compounds) or by the number of alkyl chains (double and triple chain compound).
引用
收藏
页码:427 / 443
页数:17
相关论文
共 47 条
  • [1] [Anonymous], J CHEM SOC CHEM COMM
  • [2] LIQUID-CRYSTALLINE PRIMARY BENZAMIDES
    BEGINN, U
    LATTERMANN, G
    [J]. MOLECULAR CRYSTALS AND LIQUID CRYSTALS SCIENCE AND TECHNOLOGY SECTION A-MOLECULAR CRYSTALS AND LIQUID CRYSTALS, 1994, 241 : 215 - 219
  • [3] THE LYOTROPIC LIQUID-CRYSTAL PROPERTIES OF N-OCTYL 1-O-BETA-D-GLUCOPYRANOSIDE AND RELATED N-ALKYL PYRANOSIDES
    CHUNG, YJ
    JEFFREY, GA
    [J]. BIOCHIMICA ET BIOPHYSICA ACTA, 1989, 985 (03) : 300 - 306
  • [4] Claisen L., 1913, LIEBIGS ANN CHEM, V401, P29
  • [5] COATES D, 1976, J CHEM SOC PERK T 2, P863, DOI 10.1039/p29760000863
  • [6] DUNKEL R, UNPUB
  • [7] Fischer E, 1911, LIEBIGS ANN CHEM, V383, P68
  • [8] A CARBOHYDRATE WITH A RECTANGULAR COLUMNAR PHASE
    FISCHER, H
    VILL, V
    VOGEL, C
    JESCHKE, U
    [J]. LIQUID CRYSTALS, 1993, 15 (05) : 733 - 737
  • [9] ON THE STRUCTURE OF THE THERMOTROPIC CUBIC MESOPHASES
    FISCHER, S
    FISCHER, H
    DIELE, S
    PELZL, G
    JANKOWSKI, K
    SCHMIDT, RR
    VILL, V
    [J]. LIQUID CRYSTALS, 1994, 17 (06) : 855 - 861
  • [10] FONTELL K, 1985, MOL CRYST LIQ CRYST, V1, P9