Supramolecular Explorations: Exhibiting the Extent of Extended Cationic Cyclophanes

Accounts of Chemical Research
Edward J DaleJ Fraser Stoddart

Abstract

Acting as hosts, cationic cyclophanes, consisting of π-electron-poor bipyridinium units, are capable of entering into strong donor-acceptor interactions to form host-guest complexes with various guests when the size and electronic constitution are appropriately matched. A synthetic protocol has been developed that utilizes catalytic quantities of tetrabutylammonium iodide to make a wide variety of cationic pyridinium-based cyclophanes in a quick and easy manner. Members of this class of cationic cyclophanes with boxlike geometries, dubbed Ex(n)Boxm(4+) for short, have been prepared by altering a number of variables: (i) n, the number of "horizontal" p-phenylene spacers between adjoining pyridinium units, to modulate the "length" of the cavity; (ii) m, the number of "vertical" p-phenylene spacers, to modulate the "width" of the cavity; and (iii) the aromatic linkers, namely, 1,4-di- and 1,3,5-trisubstituted units for the construction of macrocycles (ExBoxes) and macrobicycles (ExCages), respectively. This Account serves as an exploration of the properties that emerge from these structural modifications of the pyridinium-based hosts, coupled with a call for further investigation into the wealth of properties inherent in this clas...Continue Reading

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Citations

Feb 26, 2016·Journal of the American Chemical Society·Edward J DaleJ Fraser Stoddart
Apr 26, 2016·Journal of the American Chemical Society·Ryan M YoungDick T Co
Jan 14, 2017·ACS Applied Materials & Interfaces·Teng GongEn-Qing Gao
Feb 23, 2017·Journal of the American Chemical Society·Tomáš ŠolomekMichael R Wasielewski
Feb 9, 2017·Journal of the American Chemical Society·Mark C LipkeJ Fraser Stoddart
Feb 23, 2017·Journal of the American Chemical Society·Xirui GongJ Fraser Stoddart
Apr 22, 2017·Angewandte Chemie·Minh T NguyenJ Fraser Stoddart
Mar 1, 2017·Chemical Communications : Chem Comm·Leilei RuiWeian Zhang
Jan 21, 2017·Chemical Communications : Chem Comm·Ning-Ning YangEn-Qing Gao
Jul 12, 2017·The Journal of Organic Chemistry·Yago García-Rodeja, Israel Fernández
Jul 7, 2018·Angewandte Chemie·Elena PazosMarcos D García
Jul 25, 2019·Angewandte Chemie·Ommid AnamimoghadamJ Fraser Stoddart
Nov 7, 2019·Angewandte Chemie·Honghong DuanLiping Cao
Mar 13, 2020·Advanced Materials·Oliver DumeleSamuel I Stupp
Feb 13, 2020·Chemistry : a European Journal·Morten JensenJan Oskar Jeppesen
May 13, 2020·Chemical Society Reviews·Arturo Blanco-GómezMarcos D García
May 16, 2020·Angewandte Chemie·Weijian XueLyle Isaacs
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Feb 14, 2020·Angewandte Chemie·Kaidi XuChunju Li
Apr 8, 2020·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Jiahong JinLi Ren
May 4, 2017·Chemical Society Reviews·Zhichang LiuJ Fraser Stoddart
Mar 25, 2020·Chemical Science·Arturo Blanco-GómezMarcos D García
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Dec 28, 2019·Journal of Chemical Information and Modeling·Rabindranath Paul, Sandip Paul
Sep 4, 2020·Angewandte Chemie·Johnny HuHenri-Pierre Jacquot de Rouville

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