Supramolecular Chiral Helical Ribbons of Tetraphenylethylene‐Appended Naphthalenediimide Controlled by Solvent and Induced by l‐ and d‐Alanine Spacers,Chemistry - An Asian Journal

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Supramolecular Chiral Helical Ribbons of Tetraphenylethylene‐Appended Naphthalenediimide Controlled by Solvent and Induced by l‐ and d‐Alanine Spacers
Chemistry - An Asian Journal ( IF 3.5 ) Pub Date : 2018-11-26 , DOI: 10.1002/asia.201801421
Santosh P. Goskulwad _{1,

2} , Mohammad Al Kobaisi ₃ , Duong Duc La ₄ , Rajesh S. Bhosale _{1,

5} , Malavath Ratanlal ₆ , Sidhanath V. Bhosale _{1,

2} , Sheshanath V. Bhosale ₇

Affiliation

Naphthalenediimide‐tetraphenylethylene conjugates with an alanine spacer (coded as: NDI‐(Ala‐TPE)₂) were synthesized to study the influence of the chirality of the amino acid spacer on its self‐assemblies. Here we particularly show that NDI‐Ala‐TPE bearing l‐alanine gives left‐handed (M‐type) helical superstructure, while d‐alanine produces right‐handed (P‐type) helical ribbons in THF:H₂O at 40:60 % v/v ratio. However, particular aggregates were observed at 20:80 % v/v ratio. Circular dichroism was used to characterise the induction of chirality and the handedness of the helical superstructures, and the microstructure of the self‐assembled materials was visualised using scanning electron microscopy while DLS analysis confirmed the formation of particular aggregates in solution.

中文翻译：

四苯基乙烯附加的萘二甲酰亚胺的超分子手性螺旋带由溶剂控制并由l和d-丙氨酸间隔基诱导

合成了带有丙氨酸间隔基的萘二酰亚胺-四苯乙烯共轭物（编码为：NDI-（Ala-TPE）₂），以研究氨基酸间隔基的手性对其自组装的影响。在这里，我们特别表明，NDI-ALA-TPE轴承升丙氨酸给左撇子（M型）的螺旋上层建筑，而d丙氨酸产生右旋（P型）的THF螺旋带：H ₂O的v / v比为40：60％。然而，以20：80％v / v的比例观察到特定的聚集体。圆二色性用于表征手性的诱导和螺旋上层结构的顺手性，并且使用扫描电子显微镜观察自组装材料的微观结构，而DLS分析证实了溶液中特定聚集体的形成。

更新日期：2018-11-26

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