Aminomethylenehelicene Oligomers Possessing Flexible Two-Atom Linker Form a Stimuli-Responsive Double-Helix in Solution

被引：17

作者：

Shigeno, Masanori ^{[1
]}

Sato, Masahiko ^{[1
]}

Kushida, Yo ^{[1
]}

Yamaguchi, Masahiko ^{[1
]}

机构：

[1] Tohoku Univ, Grad Sch Pharmaceut Sci, Dept Organ Chem, Sendai, Miyagi 9808578, Japan

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 3卷 / 07期

基金：

日本学术振兴会;

关键词：

acid/base responses; aminomethylenehelicenes; helical structures; oligomers; thermal hysteresis; OLIGOAMIDE FOLDAMERS; MOLECULAR STRANDS; ETHYNYLHELICENE OLIGOMERS; DIMER FORMATION; POLYMERS; HELICENE; TRANSITION; INDUCTION; PEPTIDES; ROTATION;

D O I：

10.1002/ajoc.201402065

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aminomethylenehelicene oligomers up to the (M)-heptamer were synthesized by reductive amination from a formylhelicene building block. The oligomers containing more than three helicenes formed a double helix in 1,3-dilfuorobenzene. The (M)tetramer and (M)-pentamer unfolded into a random coil by heating to 60 degrees C, whereas the (M)-hexamer only slightly unfolded at the same temperature. A two-sided thermal hysteresis was detected in the structural change of the (M)-tetramer and (M)-pentamer during cooling and heating. The (M)-pentamer and (M)-hexamer unfolded with the addition of trifluoroacetic acid and regenerated a double helix with the addition of triethylamine.

引用

页码：797 / 804

页数：8