Striking correlation between the unusual trigonal crystal packing and the ability to self-assemble into nanofibers of 2,3-di-n-alkyloxyanthracenes.
The space group of the crystals of derivatives of 2,3-dialkoxyanthracenes is monoclinic P2(1)/a (herringbone structure) with the linear ethyl or propyl chains but abruptly changes to the trigonal P3 or R3 space group for butyl to heptyl chains. Strikingly, this switch is correlated with the capacity of these compounds to self-assemble into nanofibers and organogels. Besides, compounds with a chain length exceeding seven carbon atoms could not be crystallized in accordance with the analysis of the projected crystal structure but are nevertheless excellent organogelators. The study of this series of compounds suggests a tight link between the molecular structure of the crystals and that of the organogels.
Olive
Alexandre G L
AG
Université Bordeaux 1, CNRS, Institut des Sciences Moléculaires UMR 5255, Nanostructures Organiques NEO, 33405 Talence, France.
Raffy
Guillaume
G
Allouchi
Hassan
H
Léger
Jean-Michel
JM
Del Guerzo
André
A
Desvergne
Jean-Pierre
JP
D000873:Anthracenes / Q000737:chemistry*; D002725:Chloroform / Q000737:chemistry; D003460:Crystallization; D018360:Crystallography, X-Ray / Q000379:methods; D005782:Gels; D008422:Materials Testing; D018613:Microscopy, Confocal / Q000379:methods; D008856:Microscopy, Fluorescence / Q000379:methods; D008956:Models, Chemical; D008968:Molecular Conformation; D057139:Nanofibers / Q000737:chemistry*; D036103:Nanotechnology / Q000379:methods*; D013059:Spectrum Analysis, Raman / Q000379:methods; D013499:Surface Properties
D000873:Anthracenes; D005782:Gels; D002725:Chloroform