Evidence of Nanotubular Self-Organization in Solution and Solid States of Heterochiral Cyclo 1:1 [α/α-Nα-Bn-hydrazino]mers Series

被引：10

作者：

Moussodia, Ralph-Olivier ^{[1
]}

Acherar, Samir ^{[1
]}

Romero, Eugenie ^{[1
]}

Didierjean, Claude ^{[2
]}

Jamart-Gregoire, Brigitte ^{[1
]}

机构：

[1] Univ Lorraine, CNRS, UMR 7375, LCPM, F-54001 Nancy, France

[2] Univ Lorraine, CNRS, UMR 7036,Fac Sci & Technol, Lab Crystallog Resonance Magnet & Modelisat CRM2, F-54506 Vandoeuvre Les Nancy, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 06期

关键词：

ASSEMBLING ORGANIC NANOTUBES; AMINO-ACID; CONFORMATIONAL-ANALYSIS; CHOLESTEROL-STILBENE; BETA-PEPTIDES; GAMMA-TURNS; TETRAPEPTIDE; FOLDAMERS; STACKING; DYNAMICS;

D O I：

10.1021/jo502684g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The cyclization of heterochiral 1:1 [alpha/alpha-N-alpha-Bn-hydrazino]mers leads to the corresponding cyclotetramer and cyclohexamer 3 and 4. X-ray crystallographic analysis of 3 unveils its ability to self-assemble into nanotubular structures. Further experiments conducted in the solid state through SEM analyses demonstrate the capability of 3 and 4 to form aerogels consisting of a network of nontwisted fibers, thus confirming the presence of self-organization within this series of mixed-hydrazinopeptides. Subsequent FTIR and NMR studies demonstrate the presence of an equilibrium between monomeric (intramolecular H-bonds) and nanotubular (intermolecular H-bonds) forms in solution. This equilibrium can be modified by varying the solvent.

引用

页码：3022 / 3029

页数：8

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