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      Construction of muscle-like metallo-supramolecular polymers from a pillar[5]arene-based [c2]daisy chain

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          Abstract

          A muscle-like metallo-supramolecular polymer based on a solvent-driven [ c2]daisy chain has been prepared from an amino-modified pillar[5]arene. The integration of terpyridine moieties on both ends of the [ c2]daisy chain and the stiff architecture of pillar[5]arene units facilitated the efficient formation of the metallo-supramolecular polymer.

          Abstract

          A muscle-like metallo-supramolecular polymer based on a solvent-driven [ c2]daisy chain has been prepared from an amino-modified pillar[5]arene. The integration of terpyridine moieties on both ends of the [ c2]daisy chain and the stiff architecture of pillar[5]arene units facilitated the efficient formation of the metallo-supramolecular polymer. UV/vis absorption spectroscopy, dynamic light scattering, transmission electron microscopy and scanning electron microscopy were used to characterize the self-assembly behavior of the resulting polymer chains. From proton NMR studies, we confirmed that the pillar[5]arene-based [ c2]daisy chain could change its length continuously in response to changes in the polarity of the solvent. Consequently, the metallo-supramolecular polymer could change its length continuously according to the solvent polarity based on the individual contraction or extension of each daisy chain repeating unit. The current system can serve as a platform to mimic the muscle movement.

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          Pillararenes, a new class of macrocycles for supramolecular chemistry.

          Min Xue, Yong Yang, Xiaodong Chi … (2012)
          Because of the importance of novel macrocycles in supramolecular science, interest in the preparation of these substances has grown considerably. However, the discovery of a new class of macrocycles presents challenges because of the need for routes to further functionalization of these molecules and good host-guest complexation. Furthermore, useful macrocylic hosts must be easily synthesized in large quantities. With these issues in mind, the recently discovered pillararenes attracted our attention. These macrocycles contain hydroquinone units linked by methylene bridges at para positions. Although the composition of pillararenes is similar to that of calixarenes, they have different structural characteristics. One conformationally stable member of this family is pillar[5]arene, which consists of five hydroquinone units. The symmetrical pillar architecture and electron-donating cavities of these macrocycles are particularly intriguing and afford them with some special and interesting physical, chemical, and host-guest properties. Due to these features and their easy accessibility, pillararenes, especially pillar[5]arenes, have been actively studied and rapidly developed within the last 4 years. In this Account, we provide a comprehensive overview of pillararene chemistry, summarizing our results along with related studies from other researchers. We describe strategies for the synthesis, isomerization, and functionalization of pillararenes. We also discuss their macrocyclic cavity sizes, their host-guest properties, and their self-assembly into supramolecular polymers. The hydroxyl groups of the pillararenes can be modified at all positions or selectively on one or two positions. Through a variety of functionalizations, researchers have developed many pillararene derivatives that exhibit very interesting host-guest properties both in organic solvents and in aqueous media. Guest molecules include electron acceptors such as viologen derivatives and (bis)imidazolium cations and alkyl chain derivatives such as n-hexane, alkanediamines, n-octyltrimethyl ammonium, and neutral bis(imidazole) derivatives. These host-guest studies have led to the fabrication of (pseudo)rotaxanes or poly(pseudo)rotaxanes, supramolecular dimers or polymers, artificial transmembrane proton channels, fluorescent sensors, and other functional materials.
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            Formation of Linear Supramolecular Polymers That Is Driven by CH⋅⋅⋅π Interactions in Solution and in the Solid State

            Feihe Huang, Yihua Yu, Zhi Z. Ma … (2011)
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              Sequence-specific peptide synthesis by an artificial small-molecule machine.

              Bartosz Lewandowski, Guillaume De Bo, John Ward … (2013)
              The ribosome builds proteins by joining together amino acids in an order determined by messenger RNA. Here, we report on the design, synthesis, and operation of an artificial small-molecule machine that travels along a molecular strand, picking up amino acids that block its path, to synthesize a peptide in a sequence-specific manner. The chemical structure is based on a rotaxane, a molecular ring threaded onto a molecular axle. The ring carries a thiolate group that iteratively removes amino acids in order from the strand and transfers them to a peptide-elongation site through native chemical ligation. The synthesis is demonstrated with ~10(18) molecular machines acting in parallel; this process generates milligram quantities of a peptide with a single sequence confirmed by tandem mass spectrometry.
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                Author and article information

                Journal
                Journal ID (publisher-id): PCOHC2
                Title: Polym. Chem.
                Abbreviated Title: Polym. Chem.
                Publisher: Royal Society of Chemistry (RSC)
                ISSN (Print): 1759-9954
                ISSN (Electronic): 1759-9962
                Publication date Created: 2014
                Publication date (Electronic): 2014
                Volume: 5
                Issue: 19
                Pages: 5734-5739
                Affiliations
                [1 ]State Key Laboratory of Chemical Engineering
                [2 ]Department of Chemistry
                [3 ]Zhejiang University
                [4 ]Hangzhou 310027, P.R. China
                Article
                DOI: 10.1039/C4PY00733F
                SO-VID: 0681a5bb-2fd0-4219-b565-b55ec49ebe8f
                Copyright © © 2014
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