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      Polyaromatic molecular tubes: from strategic synthesis to host functions

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          Abstract

          This feature article describes the recent progress in the synthesis and application of short tubular molecules bearing multiple (≥3) polyaromatic rings ( e.g., anthracene, pyrene, chrysene, anthanthrenylene, and HBC). These polyaromatic tubes display characteristic properties such as strong fluorescent emission, a selective molecular binding ability, efficient host–guest energy transfer and open–closed structural transformations.

          Abstract

          Ring- and tube-shaped molecules like crown ethers and cyclodextrins play a fundamental role in supramolecular chemistry since their initial discovery. To date, numerous intriguing properties and reactivities have been reported based on their unique inner microenvironments. While inner spaces encircled by aliphatic and/or small aromatic frameworks have been heavily investigated, tubular structures that feature polyaromatic frameworks remained largely unexplored until 2010, despite their undisputable potential. Polyaromatic rings provide appealing photophysical and electrochemical properties and thus allow for the construction of new functional cylindrical nanospaces. This feature article describes the recent progress in the synthesis and application of short tubular molecules bearing multiple (≥3) polyaromatic rings ( e.g., anthracene, pyrene, chrysene, and HBC). The polyaromatic tubes reported herein display characteristic properties such as strong fluorescent emission, a selective molecular binding ability, efficient host–guest energy transfer and open–closed structural transformations.

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          Most cited references62

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          The cucurbit[n]uril family.

          In 1981, the macrocyclic methylene-bridged glycoluril hexamer (CB[6]) was dubbed "cucurbituril" by Mock and co-workers because of its resemblance to the most prominent member of the cucurbitaceae family of plants--the pumpkin. In the intervening years, the fundamental binding properties of CB[6]-high affinity, highly selective, and constrictive binding interactions--have been delineated by the pioneering work of the research groups of Mock, Kim, and Buschmann, and has led to their applications in waste-water remediation, as artificial enzymes, and as molecular switches. More recently, the cucurbit[n]uril family has grown to include homologues (CB[5]-CB[10]), derivatives, congeners, and analogues whose sizes span and exceed the range available with the alpha-, beta-, and gamma-cyclodextrins. Their shapes, solubility, and chemical functionality may now be tailored by synthetic chemistry to play a central role in molecular recognition, self-assembly, and nanotechnology. This Review focuses on the synthesis, recognition properties, and applications of these unique macrocycles.
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            Cucurbiturils: from synthesis to high-affinity binding and catalysis.

            In the wide area of supramolecular chemistry, cucurbit[n]urils (CBn) present themselves as a young family of molecular containers, able to form stable complexes with various guests, including drug molecules, amino acids and peptides, saccharides, dyes, hydrocarbons, perfluorinated hydrocarbons, and even high molecular weight guests such as proteins (e.g., human insulin). Since the discovery of the first CBn, CB6, the field has seen tremendous growth with respect to the synthesis of new homologues and derivatives, the discovery of record binding affinities of guest molecules in their hydrophobic cavity, and associated applications ranging from sensing to drug delivery. In this review, we discuss in detail the fundamental properties of CBn homologues and their cyclic derivatives with a focus on their synthesis and their applications in catalysis.
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              Supramolecular Chemistry

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                Author and article information

                Journal
                CHCOFS
                Chemical Communications
                Chem. Commun.
                Royal Society of Chemistry (RSC)
                1359-7345
                1364-548X
                2018
                2018
                : 54
                : 26
                : 3195-3206
                Affiliations
                [1 ]Faculty of Engineering
                [2 ]University of Yamanashi
                [3 ]Kofu 400-8511
                [4 ]Japan
                [5 ]Laboratory for Chemistry and Life Science
                [6 ]Institute of Innovative Research
                [7 ]Tokyo Institute of Technology
                [8 ]Yokohama 226-8503
                Article
                10.1039/C8CC00799C
                d74e9c36-36b2-4c80-a80b-a90f3f60f0df
                © 2018

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

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