Amphiphilic molecular gels from omega-aminoalkylated L-glutamic acid derivatives with unique chiroptical properties.
Self-assembling amphiphiles with unique chiroptical properties were derived from L-glutamic acid through omega-aminoalkylation and double long-chain alkylation. These amphiphiles can disperse in various solvents ranging from water to n-hexane. TEM and SEM observations indicate that the improvement in dispersity is induced by the formation of tubular and/or fibrillar aggregates with nanosized diameters, which makes these amphiphiles similar to aqueous lipid membrane systems. Spectroscopic observations, such as UV-visible and CD spectroscopies indicate that the aggregates are constructed on the basis of S- and R-chirally ordered structures through interamide interactions in water and organic media, respectively, and that these chiroptical properties can be controlled thermotropically and lyotropically. It is also reported that the chiral assemblies provide specific binding sites for achiral molecules and then induce chirality for the bonded molecules. Further, the applicability of the amphiphiles to template polymerization is discussed.
Kira
Yoshiko
Y
Department of Applied Chemistry and Biochemistry, Kumamoto University, 2-39-1 Kurokami, Kumamoto, 860-8555, Japan.
Okazaki
Yutaka
Y
Sawada
Tsuyoshi
T
Takafuji
Makoto
M
Ihara
Hirotaka
H
D002942:Circular Dichroism; D005782:Gels / Q000737:chemistry*; D018698:Glutamic Acid / Q000031:analogs & derivatives* / Q000737:chemistry; D006586:Hexanes; D046529:Microscopy, Electron, Transmission; D012997:Solvents; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism; D013501:Surface-Active Agents / Q000737:chemistry*; D014867:Water
D005782:Gels; D006586:Hexanes; D012997:Solvents; D013501:Surface-Active Agents; D014867:Water; C026385:n-hexane; D018698:Glutamic Acid