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      Supramolecular delivery systems based on pillararenes

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          Abstract

          This article summarizes pillararene-based supramolecular delivery systems constructed through host–guest interactions and outlines the future challenges for their broader applications.

          Abstract

          Supramolecular delivery systems (SDSs) fabricated via molecular assembly, which conveniently allow integration of multiple functions in a single system and structural diversity of systems, are a very active research area due to their enormous potential in biomedical applications, including drug delivery, cell imaging, diagnosis, and release monitoring. Pillararenes, a novel type of macrocyclic molecule, are gaining increasing interest as an important component in the construction of SDSs due to their unique structural and chemical properties. This feature article summarizes pillararene-based SDSs constructed via host–guest interactions via four strategies: (1) supramolecular host–guest complexation; (2) self-assembly of supramolecular amphiphiles; (3) self-assembly of amphiphilic supramolecular polymer conjugates; (4) hybridization with other porous materials, such as inorganic materials and metal-organic frameworks (MOFs). The various SDSs based on pillararenes for the delivery of different cargoes from anti-cancer drugs, fluorescent molecules, siRNAs, and insulin to antibiotics are reviewed. Furthermore, future challenges for advanced SDSs based on pillararenes and their broader applications are outlined.

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          para-Bridged symmetrical pillar[5]arenes: their Lewis acid catalyzed synthesis and host-guest property.

          Tomoki Ogoshi, Suguru Kanai, Shuhei Fujinami … (2008)
          Condensation of 1,4-dimethoxybenzene (DMB) with paraformaldehyde in the presence of BF3.O(C2H5)2 gave novel para-bridged pentacyclic pillar DMB (DMpillar[5]arene). Moreover, para-bridged pentacyclic hydroquinone (pillar[5]arene) was prepared. Pillar[5]arene formed 1:1 host-guest complexes with dialkyl viologen and alkyl pyridinium derivatives. However, pillar[5]arene did not form complexes with the diadamantyl viologen derivative since a bulky adamantyl group was unable to thread the cavity of pillar[5]arene.
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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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              Emerging Multifunctional Metal-Organic Framework Materials.

              Bin Li, Yuanjing Cui, Hui-Min Wen … (2016)
              Metal-organic frameworks (MOFs), also known as coordination polymers, represent an interesting type of solid crystalline materials that can be straightforwardly self-assembled through the coordination of metal ions/clusters with organic linkers. Owing to the modular nature and mild conditions of MOF synthesis, the porosities of MOF materials can be systematically tuned by judicious selection of molecular building blocks, and a variety of functional sites/groups can be introduced into metal ions/clusters, organic linkers, or pore spaces through pre-designing or post-synthetic approaches. These unique advantages enable MOFs to be used as a highly versatile and tunable platform for exploring multifunctional MOF materials. Here, the bright potential of MOF materials as emerging multifunctional materials is highlighted in some of the most important applications for gas storage and separation, optical, electric and magnetic materials, chemical sensing, catalysis, and biomedicine.
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                Author and article information

                Journal
                Journal ID (publisher-id): CHCOFS
                Title: Chemical Communications
                Abbreviated Title: Chem. Commun.
                Publisher: Royal Society of Chemistry (RSC)
                ISSN (Print): 1359-7345
                ISSN (Electronic): 1364-548X
                Publication date Created: December 4 2018
                Publication date (Electronic): 2018
                Volume: 54
                Issue: 97
                Pages: 13626-13640
                Affiliations
                [1 ]Shaanxi Key Laboratory of Natural Products & Chemical Biology
                [2 ]College of Chemistry & Pharmacy
                [3 ]Northwest A&F University
                [4 ]Yangling
                [5 ]Shaanxi 712100
                Article
                DOI: 10.1039/C8CC08252A
                SO-VID: 93c29888-edb5-4dfa-bc70-f30c9e0cf598
                Copyright © © 2018
                License:

                http://rsc.li/journals-terms-of-use

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