Novel chiral molecular tweezer from (+)-usnic acid.
A new chiral molecular tweezer was synthesized with (1R,2R)-1,2-diaminocyclohexane as spacer and two molecules of (+)-usnic acid as pincers. The ability of this molecular tweezer to bind 2,4,7-trinitrofluorenone was studied. A charge-transfer complex was formed in which TNF was sandwiched between the two usnic acid units with pi-pi-stacked aromatic interactions.
Legouin
Béatrice
B
EA Substances Lichéniques et Photoprotection, Faculté des Sciences Biologiques et Pharmaceutiques, Université de Rennes 1, 2 avenue du Professeur Léon Bernard, F-35043 Rennes Cedex, France.
Uriac
Philippe
P
Tomasi
Sophie
S
Toupet
Loïc
L
Bondon
Arnaud
A
van de Weghe
Pierre
P
D001572:Benzofurans / Q000737:chemistry*; D001665:Binding Sites; D018360:Crystallography, X-Ray; D003510:Cyclohexanes / Q000737:chemistry; D005449:Fluorenes / Q000737:chemistry; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism
D001572:Benzofurans; D003510:Cyclohexanes; D005449:Fluorenes; D006576:Heterocyclic Compounds, 4 or More Rings; C073339:usnic acid; C005644:2,4,7-trinitrofluorenone