Tuning methyl 4,6-O-benzylidene α-D-glucopyranosides' gelation ability by minor group modifications

被引:17
作者
Abreu, Marlon F. [1 ]
Salvador, Vitor T. [1 ]
Vitorazi, Leticia [1 ]
Gatts, Carlos E. N. [2 ]
dos Santos, Denise R. [2 ]
Giacomini, Rosana [2 ]
Cardoso, Sergio L. [2 ]
Miranda, Paulo C. M. L. [1 ]
机构
[1] Univ Estadual Campinas, UNICAMP, Inst Chem, BR-13083970 Campinas, SP, Brazil
[2] No State Univ Rio Janeiro, UENF, Campos Dos Goytacazes, RJ, Brazil
基金
巴西圣保罗研究基金会;
关键词
LMOG; SAFIN; Organogelators; Self-assembly; SUGAR-INTEGRATED GELATORS; LOW-MOLECULAR-MASS; ORGANIC-SOLVENTS; REMARKABLE DIVERSITY; DUAL-COMPONENT; SOFT MATTER; OIL-SPILLS; GELS; ORGANOGELS; LIQUIDS;
D O I
10.1016/j.carres.2012.03.021
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Ten methyl 4,6-O-benzylidene alpha-D-glucopyranosides were synthesized for the purpose of studying systematically the effect of small group changes at position 4 of the aromatic ring on the ability to gelate organic solvents. The gelation properties are discussed on the basis of small angle X-ray scattering (SAXS), Fourier transform infrared spectroscopy (FTIR), differential scanning calorimetry (DSC) measurements, and scanning electron microscopy (SEM) observations. Sol-gel transition temperatures were determined simultaneously by DSC and temperature-dependent FTIR measurements. The current study emphasizes that carbohydrates furnish not only valuable information about structural requirements for organogelator design, but also for molecular assembly systems in general. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:69 / 78
页数:10
相关论文
共 54 条
[1]   New sugar-based gelators with an amino group, the gelation ability of which is remarkably reinforced by the hydrogen bond and the metal coordination [J].
Amanokura, N ;
Kanekiyo, Y ;
Shinkai, S ;
Reinhoudt, DN .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1999, (10) :1995-2000
[2]   Synthesis, self-assembly and characterization of a new glucoside-type hydrogel having a Schiff base on the aglycon [J].
Bao, CY ;
Lu, R ;
Jin, M ;
Xue, PC ;
Tan, CH ;
Zhao, YY ;
Liu, GF .
CARBOHYDRATE RESEARCH, 2004, 339 (07) :1311-1316
[3]   Impressive gelation in organic solvents by synthetic, low molecular mass, self-organizing urethane amides of L-phenylalanine [J].
Bhattacharya, S ;
Acharya, SNG .
CHEMISTRY OF MATERIALS, 1999, 11 (11) :3121-3132
[4]   First report of phase selective gelation of oil from oil/water mixtures. Possible implications toward containing oil spills [J].
Bhattacharya, S ;
Krishnan-Ghosh, Y .
CHEMICAL COMMUNICATIONS, 2001, (02) :185-186
[5]   Solvent Effect on 1,2-O-(1-Ethylpropylidene)-α-D-glucofuranose Organogel Properties [J].
Bielejewski, M. ;
Lapinski, A. ;
Luboradzki, R. ;
Tritt-Goc, J. .
LANGMUIR, 2009, 25 (14) :8274-8279
[6]  
Carretti E, 2005, SOFT MATTER, V1, P17, DOI 10.1039/b501033k
[7]   Synthesis and structural analysis of a series of D-glucose derivatives as low molecular weight gelators [J].
Cheuk, Sherwin ;
Stevens, Edwin D. ;
Wang, Guijun .
CARBOHYDRATE RESEARCH, 2009, 344 (04) :417-425
[8]   Solvent-tuned multiple self-assembly of a new sugar-appended gelator [J].
Cui, Jiaxi ;
Zheng, Jia ;
Qiao, Wenqiang ;
Wan, Xinhua .
JOURNAL OF COLLOID AND INTERFACE SCIENCE, 2008, 326 (01) :267-274
[9]   Tuning the Helicity of Self-Assembled Structure of a Sugar-Based Organogelator by the Proper Choice of Cooling Rate [J].
Cui, Jiaxi ;
Liu, Anhua ;
Guan, Yan ;
Zheng, Jia ;
Shen, Zhihao ;
Wan, Xinhua .
LANGMUIR, 2010, 26 (05) :3615-3622
[10]   Supramolecular gelling agents: can they be designed? [J].
Dastidar, Parthasarathi .
CHEMICAL SOCIETY REVIEWS, 2008, 37 (12) :2699-2715