Chiromers: conformation-driven mirror-image supramolecular chirality isomerism identified in a new class of helical rosette nanotubes

被引:20
|
作者
Hemraz, Usha D. [1 ,2 ]
El-Bakkari, Mounir [1 ,2 ]
Yamazaki, Takeshi [1 ,2 ]
Cho, Jae-Young [2 ]
Beingessner, Rachel L. [2 ]
Fenniri, Hicham [1 ,2 ,3 ,4 ]
机构
[1] Univ Alberta, Dept Chem, Edmonton, AB, Canada
[2] Natl Inst Nanotechnol, Edmonton, AB T6G 2M9, Canada
[3] Northeastern Univ, Dept Chem & Biomed Engn, Boston, MA 02115 USA
[4] Qatar Biomed Res Inst, Biomed Engn Res Ctr, Doha, Qatar
关键词
MOLECULAR-STRUCTURE; SHAPED MOLECULES; SERGEANTS;
D O I
10.1039/c4nr00340c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Rosette nanotubes are biologically inspired nanostructures, formed through the hierarchical organization of a hybrid DNA base analogue (GAC), which features hydrogen-bonding arrays of guanine and cytosine. Several twin-GAC 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-GAC 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.
引用
收藏
页码:9421 / 9427
页数:7
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