Synthesis, structure and stimulus-responsive properties of a metallogel of a designer ferrocene appended peptide mimetic†

IF 3.2 3区工程技术 Q2 CHEMISTRY, PHYSICAL

Molecular Systems Design & Engineering Pub Date : 2023-03-29 DOI:10.1039/D2ME00273F

Olamilekan Joseph Ibukun, Milan Gumtya, Surajit Singh, Ananda Shit, M. Douzapau and Debasish Haldar

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Abstract

This study reports a simple protocol for the synthesis of ferrocene substituted benzoic acid and an efficient synthetic approach towards a ferrocene appended peptide mimetic with a high reaction rate, yield and purity. From X-ray single crystal analysis, the ferrocene appended peptide mimetic adopts an extended conformation and self-aggregates to form a dimer structure by intermolecular hydrogen bonds. The dimer formation is also supported by mass spectrometry. In higher order packing, the dimeric subunits further self-assembled to form a complex sheet-like structure stabilized by multiple π–π stacking interactions between the phenyl and cyclopentandienyl rings of ferrocene. Moreover, the ferrocene appended peptide mimetic forms a stimulus-responsive metallogel in DMF–water. The rheology experiments support the formation of a strong gel. The metallogel burst on addition of other salts such as Cu(OAc)₂·4H₂O, Pb(OAc)₂, Zn(OAc)₂·2H₂O, Cd(OAc)₂·4H₂O, and Mn(OAc)₂·4H₂O. The metallogel is responsive to pH. On addition of triethylamine the metallogel turned into a golden yellow solution. However, on further addition of trifluoroacetic acid the metallogel reappeared.

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二茂铁附加肽模拟物金属凝胶的合成、结构和刺激响应性能

本研究报道了二茂铁取代苯甲酸的简单合成方案和二茂铁附加肽的高效合成方法，具有较高的反应速率、产率和纯度。x射线单晶分析表明，二茂铁附加肽模拟物采用延伸构象，并通过分子间氢键自聚集形成二聚体结构。质谱分析也证实了二聚体的形成。在高阶填料中，二聚体亚基进一步自组装形成复杂的片状结构，通过二茂铁的苯基环和环戊二烯环之间的多重π -π堆叠相互作用来稳定结构。此外，二茂铁附加肽模拟物在dmf -水中形成刺激响应的金属凝胶。流变学实验支持强凝胶的形成。在Cu(OAc)2·4H2O、Pb(OAc)2、Zn(OAc)2·2H2O、Cd(OAc)2·4H2O、Mn(OAc)2·4H2O等盐的作用下，金属凝胶破裂。该金属凝胶对ph值有反应。加入三乙胺后，该金属凝胶变成金黄色溶液。然而，当进一步加入三氟乙酸时，金属凝胶重新出现。

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来源期刊

Molecular Systems Design & Engineering Engineering-Biomedical Engineering

CiteScore

6.40

自引率

2.80%

发文量

144

期刊介绍： Molecular Systems Design & Engineering provides a hub for cutting-edge research into how understanding of molecular properties, behaviour and interactions can be used to design and assemble better materials, systems, and processes to achieve specific functions. These may have applications of technological significance and help address global challenges.