Self-assembled spiral nanoarchitecture and supramolecular chirality in Langmuir-Blodgett films of an achiral amphiphilic barbituric acid.
An amphiphilic barbituric acid derivative was found to form stable monolayers showing a clear phase transition at the air/water interface. It is interesting to find that the deposited Langmuir-Blodgett (LB) films of the compound showed circular dichroism (CD) although the molecule itself was achiral. AFM measurements on the transferred one-layer LB film revealed that spiral nanoarchitectures were formed. It was further found that the supramolecular chirality of the LB films was related to symmetry breaking at the interface. Hydrogen bonding and the pi-pi stacking between the neighboring molecules resulted in chiral fibers which formed the spiral structures. To the best of our knowledge, this is the first report on the chirality of the molecular assemblies and spiral nanostructures formed through the air/water interface by achiral molecules.
Huang
Xin
X
CAS Key Laboratory of Colloid and Interface Science, Institute of Chemistry, CAS, 100080 Beijing, PR China.
Li
Chao
C
Jiang
Siguang
S
Wang
Xuesong
X
Zhang
Baowen
B
Liu
Minghua
M
D001463:Barbiturates / Q000737:chemistry*; D002942:Circular Dichroism; D006860:Hydrogen Bonding; D018625:Microscopy, Atomic Force; D008968:Molecular Conformation; D036103:Nanotechnology / Q000379:methods*; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism; D013499:Surface Properties
D001463:Barbiturates; C032232:barbituric acid