A family of strong low-molecular-weight organogelators based on aminoacid derivatives

被引:37
作者
Brosse, N
Barth, D
Jamart-Grégoire, B
机构
[1] ENSIC INPL, Lab Chim Phys Macromol, UMR 7568, F-54001 Nancy, France
[2] ENSIC INPL, Lab Thermodynam Milieux Polyphases, F-54001 Nancy, France
关键词
organogel; organogelator; electronic microscopy;
D O I
10.1016/j.tetlet.2004.10.139
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new family of potent aminoacid-type organogelators obtained via an easy and unexpensive way is described. We demonstrated that structural variations onto the side chains of the aminoacid derivatives allowed modulations of the gelation properties. The organogelators bearing a benzyl or an isopropyl group (compounds 1e, 2a, and 2c) are able to provide gelation of apolar solvents at very low concentration ( less than or equal to 0.2 wt%) and to form thermostable gels. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:9521 / 9524
页数:4
相关论文
共 24 条
[1]   Minimalist peptidomimetic cyclophanes as strong organogelators [J].
Becerril, J ;
Burguete, MI ;
Escuder, B ;
Luis, SV ;
Miravet, JF ;
Querol, M .
CHEMICAL COMMUNICATIONS, 2002, (07) :738-739
[2]  
BECERRIL J, 1992, J CHEM SOC CHEM COMM, P1371
[3]   Rheology and thermotropic properties of bis-urea-based organogels in various primary alcohols [J].
Brinksma, J ;
Feringa, BL ;
Kellogg, RM ;
Vreeker, R ;
van Esch, J .
LANGMUIR, 2000, 16 (24) :9249-9255
[4]   Preparation of multiply protected alkylhydrazine derivatives by mitsunobu and PTC approaches [J].
Brosse, N ;
Pinto, MF ;
Jamart-Grégoire, B .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (24) :4757-4764
[5]   New synthesis of 1,1-substituted hydrazines by alkylation of N-acyl- or N-alkyloxycarbonylaminophthalimide using the Mitsunobu protocol [J].
Brosse, N ;
Pinto, MF ;
Jamart-Grégoire, B .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (14) :4370-4374
[6]   A new synthetic route to protected α-hydrazinoesters in high optical purity using the Mitsunobu protocol [J].
Brosse, N ;
Pinto, MF ;
Bodiguel, J ;
Jamart-Grégoire, B .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (08) :2869-2873
[7]   Hydrazinoazadipeptides as aromatic solvent gelators [J].
Carré, A ;
Le Grel, P ;
Baudy-Floc'h, M .
TETRAHEDRON LETTERS, 2001, 42 (10) :1887-1889
[8]  
de Loos M, 2001, ANGEW CHEM INT EDIT, V40, P613, DOI 10.1002/1521-3773(20010202)40:3<613::AID-ANIE613>3.0.CO
[9]  
2-K
[10]   Water gelation by small organic molecules [J].
Estroff, LA ;
Hamilton, AD .
CHEMICAL REVIEWS, 2004, 104 (03) :1201-1217