Positional Isomers of Chromophore–Peptide Conjugates Self‐Assemble into Different Morphologies,Chemistry - A European Journal

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Positional Isomers of Chromophore–Peptide Conjugates Self‐Assemble into Different Morphologies
Chemistry - A European Journal ( IF 3.9 ) Pub Date : 2018-07-18 , DOI: 10.1002/chem.201801545
Urszula Lewandowska ₁ , Stefano Corra ₁ , Wojciech Zajaczkowski ₂ , Nellie A. K. Ochs ₁ , Michal S. Shoshan ₁ , Junki Tanabe _{1,

3} , Sebastian Stappert ₂ , Chen Li ₂ , Eiji Yashima ₃ , Wojciech Pisula _{2,

4} , Klaus Müllen _{2,

5} , Helma Wennemers ₁

Affiliation

Ordering π‐systems into defined supramolecular structures is important for the development of organic functional materials. In recent years, peptides with defined secondary structures and/or self‐assembly properties were introduced as powerful tools to order peptide–chromophore conjugates into different morphologies. This work explores whether or not the directionality of peptides can be used to control the self‐assembly. The position of the π‐system in conjugates between oligoprolines and perylene monoimide (PMI) chromophores was varied by attaching the PMI moiety to the second‐to‐last residue from the C‐ and N‐termini, respectively. Microscopic and diffraction analysis revealed that the positional isomers form distinctly different supramolecular architectures that extend into the micrometer regime. NMR spectroscopic studies in solution phase allowed correlation of the self‐assembly properties with markedly different conformational preferences of the isomeric building blocks. These insights enabled the design of building blocks with predictable self‐assembly properties. Thus, the directionality of peptides offers exciting opportunities for controlling the self‐assembly and electronic properties of π‐systems.

中文翻译：

发色团-肽的位置异构体可自组装成不同的形态

将π系统排列成定义的超分子结构对于有机功能材料的开发很重要。近年来，具有定义的二级结构和/或自组装特性的肽作为强大的工具被引入，可以将肽-发色团缀合物定序为不同的形态。这项工作探讨了肽的方向性是否可用于控制自组装。通过将PMI部分分别连接到C和N末端的倒数第二个残基上，可以改变olipro脯氨酸和per单酰亚胺（PMI）生色团之间的共轭体系中π系统的位置。显微镜和衍射分析表明，位置异构体形成了截然不同的超分子结构，并延伸到微米范围。溶液相的NMR光谱研究使自组装特性与异构体结构单元的构象偏好显着不同相关。这些见解使具有可预测的自组装特性的构建基块的设计成为可能。因此，肽的方向性为控制π系统的自组装和电子性质提供了令人兴奋的机会。

更新日期：2018-07-18

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