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To this end, shape\u2010persistent macrocycles were designed with alternating carbazoles and triazoles to program a one\u2010pot synthesis and to bind large anions. The macrocycles bind anions that were once considered too weak to be coordinated, such as PF<jats:sub>6<\/jats:sub><jats:sup>\u2212<\/jats:sup>, with surprisingly high affinities (<jats:italic>\u03b2<\/jats:italic><jats:sub>2<\/jats:sub>=10<jats:sup>11<\/jats:sup>\u2009<jats:sc>M<\/jats:sc><jats:sup>\u22122<\/jats:sup> in 80:20 chloroform\/methanol) and positive cooperativity, <jats:italic>\u03b1<\/jats:italic>=(4\u2005<jats:italic>K<\/jats:italic><jats:sub>2<\/jats:sub>\/<jats:italic>K<\/jats:italic><jats:sub>1<\/jats:sub>)=1200. We also discovered that the macrocycles assemble into ultrathin films of hierarchically ordered tubes on graphite surfaces. The remarkable surface\u2010templated self\u2010assembly properties, as was observed by using scanning tunneling microscopy, are attributed to the complementary pairing of alternating triazoles and carbazoles inscribed into both the co\u2010facial and edge\u2010sharing seams that exist between shape\u2010persistent macrocycles. The multilayer assembly is also consistent with the high degree of molecular self\u2010association observed in solution, with self\u2010association constants of <jats:italic>K<\/jats:italic>=300\u2009000\u2009<jats:sc>M<\/jats:sc><jats:sup>\u22121<\/jats:sup> (chloroform\/methanol 80:20). Scanning tunneling microscopy data also showed that surface assemblies readily sequester iodide anions from solution, modulating their assembly. This multifunctional macrocycle provides a foundation for materials composed of hierarchically organized and nanotubular self\u2010assemblies.<\/jats:p>","DOI":"10.1002\/chem.201503161","type":"journal-article","created":{"date-parts":[[2015,11,23]],"date-time":"2015-11-23T07:40:03Z","timestamp":1448264403000},"page":"560-569","source":"Crossref","is-referenced-by-count":79,"title":["Multifunctional Tricarbazolo Triazolophane Macrocycles: One\u2010Pot Preparation, Anion Binding, and Hierarchical Self\u2010Organization of Multilayers"],"prefix":"10.1002","volume":"22","author":[{"given":"Semin","family":"Lee","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Brandon E.","family":"Hirsch","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yun","family":"Liu","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"James 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