Chiromers: conformation-driven mirror-image supramolecular chirality isomerism identified in a new class of helical rosette nanotubes.
Rosette nanotubes are biologically inspired nanostructures, formed through the hierarchical organization of a hybrid DNA base analogue (G∧C), which features hydrogen-bonding arrays of guanine and cytosine. Several twin-G∧C motifs functionalized with chiral moieties, which undergo a self-assembly process under methanolic and aqueous conditions to produce helical rosette nanotubes (RNTs), were synthesized and characterized. The built-in molecular chirality in the twin-G∧C building blocks led to the supramolecular chirality exhibited by the RNTs, as evidenced by the CD activity. Depending on the motifs and environmental conditions, mirror-image supramolecular chirality due to absolute molecular chirality, solvent-induced and structure-dependent supramolecular chirality inversion, and pH-controlled chiroptical switching were observed.
Department of Chemistry, University of Alberta, Edmonton, Alberta, Canada.
Usha D
UD
Hemraz
Mounir
M
El-Bakkari
Takeshi
T
Yamazaki
Jae-Young
JY
Cho
Rachel L
RL
Beingessner
Hicham
H
Fenniri
D007536:Isomerism; D008958:Models, Molecular; D008968:Molecular Conformation; D036103:Nanotechnology / Q000379:methods*; D043942:Nanotubes / Q000737:chemistry* / Q000648:ultrastructure*; D013237:Stereoisomerism