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First, the cycloaddition of vinyl acetate to anthracene was optimized to, upon hydrolysis, give dibenzobarrelene derivative <jats:bold>6<\/jats:bold>, which after five functional group transformations and then cyclotrimerization gave heptiptycene dodecaester <jats:bold>4<\/jats:bold> in an overall 17\u2009% yield. Following that, compound <jats:bold>4<\/jats:bold> was converted into <jats:italic>D<\/jats:italic><jats:sub>3<jats:italic>h<\/jats:italic><\/jats:sub> symmetric <jats:bold>1<\/jats:bold>, composed of two fused cavitands each holding three terminal alkynes at the rim for conjugation to functional molecules using the highly efficient CuAAC reaction. To survey the reactivity of hexavalent <jats:bold>1<\/jats:bold>, we \u201cclicked\u201d 2\u2010acetamido\u20102\u2010deoxy\u2010\u03b2\u2010<jats:sc>d<\/jats:sc>\u2010glucopyranosyl azide 3,4,6\u2010triacetate (carbohydrate), methoxypolyethylene glycol azide (PEG, <jats:italic>M<\/jats:italic><jats:sub>n<\/jats:sub>=2000; polymer) and benzyl azide (aromatic) to obtain hexavalent conjugates <jats:bold>12<\/jats:bold>\u2013<jats:bold>14<\/jats:bold> in 50\u201379\u2009% yields. In summary, dual\u2010cavity <jats:bold>1<\/jats:bold> is an accessible, structurally\u2010unique and hexavalent host that can be \u201cclicked\u201d to a variety of functional molecules for (a)\u2005combinatorial lead identification of drugs, (b)\u2005preparation of hierarchical soft materials and (c)\u2005design of selective chemosensors, scavengers, or supramolecular catalysts.<\/jats:p>","DOI":"10.1002\/chem.201805246","type":"journal-article","created":{"date-parts":[[2018,11,22]],"date-time":"2018-11-22T11:33:17Z","timestamp":1542886397000},"page":"1242-1248","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["A Hexavalent Basket for Bottom\u2010Up Construction of Functional Soft Materials and Polyvalent Drugs through a \u201cClick\u201d Reaction"],"prefix":"10.1002","volume":"25","author":[{"given":"Taylor A.","family":"Neal","sequence":"first","affiliation":[{"name":"Department of Chemistry &amp; Biochemistry The Ohio State University  100 West 18th Avenue 43210 Columbus Ohio USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6421-2358","authenticated-orcid":false,"given":"Weikun","family":"Wang","sequence":"additional","affiliation":[{"name":"Department of Chemistry &amp; Biochemistry The Ohio State University  100 West 18th Avenue 43210 Columbus Ohio USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Lei","family":"Zhiquan","sequence":"additional","affiliation":[{"name":"Department of Chemistry &amp; Biochemistry The Ohio State University  100 West 18th Avenue 43210 Columbus Ohio USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ruojing","family":"Peng","sequence":"additional","affiliation":[{"name":"Department of Chemistry &amp; Biochemistry The Ohio State University  100 West 18th Avenue 43210 Columbus Ohio USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Priti","family":"Soni","sequence":"additional","affiliation":[{"name":"Department of Chemistry &amp; Biochemistry The Ohio State University  100 West 18th Avenue 43210 Columbus Ohio USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Han","family":"Xie","sequence":"additional","affiliation":[{"name":"Department of Chemistry &amp; Biochemistry The Ohio State University  100 West 18th Avenue 43210 Columbus Ohio USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7540-2387","authenticated-orcid":false,"given":"Jovica D.","family":"Badji\u0107","sequence":"additional","affiliation":[{"name":"Department of Chemistry &amp; Biochemistry The Ohio State University  100 West 18th Avenue 43210 Columbus Ohio USA"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2018,12,20]]},"reference":[{"key":"e_1_2_6_1_1","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3773(19981102)37:20<2754::AID-ANIE2754>3.0.CO;2-3"},{"key":"e_1_2_6_1_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3757(19981016)110:20<2908::AID-ANGE2908>3.0.CO;2-2"},{"key":"e_1_2_6_2_1","unstructured":"\u00a0"},{"key":"e_1_2_6_3_2","first-page":"345","volume-title":"Multivalency in Biological Systems in Chemical Probes in Biology (NATO Sci. 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