{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,28]],"date-time":"2026-09-28T03:39:23Z","timestamp":1790566763097,"version":"4.1.0"},"reference-count":80,"publisher":"Wiley","issue":"43","license":[{"start":{"date-parts":[[2025,9,1]],"date-time":"2025-09-01T00:00:00Z","timestamp":1756684800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/100000001","name":"National Science Foundation","doi-asserted-by":"publisher","award":["CHE\u20102304883"],"award-info":[{"award-number":["CHE\u20102304883"]}],"id":[{"id":"10.13039\/100000001","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100017170","name":"Thailand Science Research and Innovation","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100017170","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004705","name":"King Mongkut's University of Technology Thonburi","doi-asserted-by":"publisher","award":["RGNS 64\u2010094"],"award-info":[{"award-number":["RGNS 64\u2010094"]}],"id":[{"id":"10.13039\/501100004705","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2025,10,20]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>We describe the preparation, conformational dynamics, and stereoselective recognition characteristics of water\u2010soluble pillar[6]arenes <jats:italic>pS<\/jats:italic>\u2013<jats:bold>2<\/jats:bold><jats:sup>12\u2212<\/jats:sup> and <jats:italic>pR<\/jats:italic>\u2013<jats:bold>2<\/jats:bold><jats:sup>12\u2212<\/jats:sup>. These two novel and diastereomeric cavitands comprise a 2,5\u2010<jats:italic>bis<\/jats:italic>(ethoxy)pillar[6]arene core with one of six phenylene ring conjugated to two hexaanionic dendrons. Each dendron includes an (<jats:italic>S<\/jats:italic>)\u2212glutamic acid amidated with two <jats:italic>tris<\/jats:italic>\u2010carboxylic Behera's amines. Cavitands <jats:italic>pS<\/jats:italic>\u2013<jats:bold>2<\/jats:bold><jats:sup>12\u2212<\/jats:sup> and <jats:italic>pR<\/jats:italic>\u2013<jats:bold>2<\/jats:bold><jats:sup>12\u2212<\/jats:sup> were obtained in six synthetic steps and resolved by column chromatography. The results of <jats:sup>1<\/jats:sup>H NMR and circular dichroism spectroscopic measurements are in line with <jats:italic>pS<\/jats:italic>\/<jats:italic>pR<\/jats:italic>\u2013<jats:bold>2<\/jats:bold><jats:sup>12\u2212<\/jats:sup> having unidirectional orientation of alkoxy substituents (i.e., planar chirality) and no observable interconversion for, at least, 2 weeks. Computational studies supported with <jats:sup>1<\/jats:sup>H DOSY NMR measurements revealed that sufficiently bulky dendrons require high activation energy to pass through the pillararene's cylindrical cavity therefore inhibiting rotation of the phenylene holding them. With the unique and chiral binding pocket, <jats:italic>pS<\/jats:italic>\u2013<jats:bold>2<\/jats:bold><jats:sup>12\u2212<\/jats:sup> (<jats:italic>pR<\/jats:italic>\u2013<jats:bold>2<\/jats:bold><jats:sup>12\u2212<\/jats:sup>) formed inclusion complexes with cocaine adulterants levamisole and dexamisole (<jats:italic>K<\/jats:italic><jats:sub>d<\/jats:sub>\u00a0&gt;\u00a0mM), with their racemic mixture showing separate <jats:sup>1<\/jats:sup>H NMR spectroscopic resonances. In this way, dendritic pillar[6]arenes can be used as chiral shift reagents for determining enantiopurity of pharmaceuticals but also for examining a variety of chiral recognition processes, sensing of chiral molecules, and stereoselective sequestrations in aqueous media.<\/jats:p>","DOI":"10.1002\/anie.202514676","type":"journal-article","created":{"date-parts":[[2025,9,1]],"date-time":"2025-09-01T12:49:44Z","timestamp":1756730984000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Dendritic Pillar[6]Arenes with Fixed Planar Chirality for Stereoselective Inclusions in Water: A Case of Facile Differentiation of Cocaine Adulterants, Levamisole and Dexamisole"],"prefix":"10.1002","volume":"64","author":[{"given":"Nitesh","family":"Kumar","sequence":"first","affiliation":[{"name":"Department of Chemistry and Biochemistry The Ohio State University  100 West 18th Avenue Columbus OH 43210 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Pratik","family":"Karmakar","sequence":"additional","affiliation":[{"name":"Supramolecular Chemistry Research Unit Department of Chemistry Faculty of Science King Mongkut's University of Technology Thonburi  126 Pracha Uthit Road, Bang Mod, Thung Khru Bangkok 10140 Thailand"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Matthew D.","family":"Politeski","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biochemistry The Ohio State University  100 West 18th Avenue Columbus OH 43210 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alexandar R.","family":"Hansen","sequence":"additional","affiliation":[{"name":"Campus Chemical Instrument Center The Ohio State University  100 West 18th Avenue Columbus OH 43210 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Carson E.","family":"Ward","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biochemistry The Ohio State University  100 West 18th Avenue Columbus OH 43210 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Christopher","family":"Mortensen","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biochemistry The Ohio State University  100 West 18th Avenue Columbus OH 43210 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Christopher M.","family":"Hadad","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biochemistry The Ohio State University  100 West 18th Avenue Columbus OH 43210 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kornkanya","family":"Pratumyot","sequence":"additional","affiliation":[{"name":"Supramolecular Chemistry Research Unit Department of Chemistry Faculty of Science King Mongkut's University of Technology Thonburi  126 Pracha Uthit Road, Bang Mod, Thung Khru Bangkok 10140 Thailand"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7540-2387","authenticated-orcid":false,"given":"Jovica D.","family":"Badji\u0107","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biochemistry The Ohio State University  100 West 18th Avenue Columbus OH 43210 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,9]]},"reference":[{"key":"e_1_2_8_1_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.5b00765"},{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c12329"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1246\/cl.190544"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol200062j"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1039\/D1CC03778A"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c11037"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.cgd.0c00982"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2024.154941"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202308316"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.1039\/D3CC03829G"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201916285"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8OB00156A"},{"key":"e_1_2_8_13_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201702542"},{"key":"e_1_2_8_14_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-021-22880-z"},{"key":"e_1_2_8_15_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202100458"},{"key":"e_1_2_8_16_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b00277"},{"key":"e_1_2_8_17_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202001680"},{"key":"e_1_2_8_18_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c09598"},{"key":"e_1_2_8_19_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202001145"},{"key":"e_1_2_8_20_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202100934"},{"key":"e_1_2_8_21_1","doi-asserted-by":"publisher","DOI":"10.1039\/c4cc02559h"},{"key":"e_1_2_8_22_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.4c06061"},{"key":"e_1_2_8_23_1","doi-asserted-by":"publisher","DOI":"10.1039\/D3CS00939D"},{"key":"e_1_2_8_24_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-0037-1610635"},{"key":"e_1_2_8_25_1","doi-asserted-by":"publisher","DOI":"10.1039\/D1CS01061A"},{"key":"e_1_2_8_26_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemmater.3c02859"},{"key":"e_1_2_8_27_1","first-page":"28005","volume":"146","author":"Wilson C. R.","year":"2024","journal-title":"J. Am. Chem. Soc."},{"key":"e_1_2_8_28_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202007682"},{"key":"e_1_2_8_29_1","doi-asserted-by":"publisher","DOI":"10.1021\/acsami.4c11893"},{"key":"e_1_2_8_30_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo100273n"},{"key":"e_1_2_8_31_1","doi-asserted-by":"publisher","DOI":"10.1039\/c3cc49794a"},{"key":"e_1_2_8_32_1","doi-asserted-by":"publisher","DOI":"10.1038\/ncomms8590"},{"key":"e_1_2_8_33_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201200122"},{"key":"e_1_2_8_34_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-025-57461-x"},{"key":"e_1_2_8_35_1","doi-asserted-by":"publisher","DOI":"10.1039\/c3cc44672g"},{"key":"e_1_2_8_36_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202415190"},{"key":"e_1_2_8_37_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja3082523"},{"key":"e_1_2_8_38_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2023.154891"},{"key":"e_1_2_8_39_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.chempr.2022.11.019"},{"key":"e_1_2_8_40_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2023.133607"},{"key":"e_1_2_8_41_1","doi-asserted-by":"publisher","DOI":"10.1039\/D2OB01487D"},{"key":"e_1_2_8_42_1","doi-asserted-by":"publisher","DOI":"10.1039\/D4CC00772G"},{"key":"e_1_2_8_43_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202420574"},{"key":"e_1_2_8_44_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.0c00522"},{"key":"e_1_2_8_45_1","doi-asserted-by":"publisher","DOI":"10.1038\/clpt.2010.156"},{"key":"e_1_2_8_46_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6AY02015A"},{"key":"e_1_2_8_47_1","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.1326"},{"key":"e_1_2_8_48_1","doi-asserted-by":"publisher","DOI":"10.1021\/ed066p814"},{"key":"e_1_2_8_49_1","doi-asserted-by":"publisher","DOI":"10.1039\/D5CC00828J"},{"key":"e_1_2_8_50_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.4c16508"},{"key":"e_1_2_8_51_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja9806229"},{"key":"e_1_2_8_52_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules28207009"},{"key":"e_1_2_8_53_1","doi-asserted-by":"publisher","DOI":"10.1002\/3527605746.ch14"},{"key":"e_1_2_8_54_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.273.5275.627"},{"key":"e_1_2_8_55_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4CS00140K"},{"key":"e_1_2_8_56_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b01261"},{"key":"e_1_2_8_57_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202116518"},{"key":"e_1_2_8_58_1","doi-asserted-by":"publisher","DOI":"10.1039\/C005254J"},{"key":"e_1_2_8_59_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.6b00859"},{"key":"e_1_2_8_60_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201603082"},{"key":"e_1_2_8_61_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4TC01022A"},{"key":"e_1_2_8_62_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202209222"},{"key":"e_1_2_8_63_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202004003"},{"key":"e_1_2_8_64_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.266.5188.1226"},{"key":"e_1_2_8_65_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.cclet.2021.12.010"},{"key":"e_1_2_8_66_1","doi-asserted-by":"publisher","DOI":"10.1039\/D1CP05253E"},{"key":"e_1_2_8_67_1","doi-asserted-by":"publisher","DOI":"10.1002\/slct.201701762"},{"key":"e_1_2_8_68_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.clinbiochem.2025.110912"},{"key":"e_1_2_8_69_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00204-017-1947-4"},{"key":"e_1_2_8_70_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.xphs.2022.12.014"},{"key":"e_1_2_8_71_1","doi-asserted-by":"publisher","DOI":"10.1002\/ardp.19833161213"},{"key":"e_1_2_8_72_1","doi-asserted-by":"publisher","DOI":"10.1002\/dta.3227"},{"key":"e_1_2_8_73_1","doi-asserted-by":"publisher","DOI":"10.1002\/dta.2505"},{"key":"e_1_2_8_74_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0731-7085(00)00513-6"},{"key":"e_1_2_8_75_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00214a063"},{"key":"e_1_2_8_76_1","doi-asserted-by":"publisher","DOI":"10.1039\/C0CS00062K"},{"key":"e_1_2_8_77_1","doi-asserted-by":"publisher","DOI":"10.1039\/D3CC05485C"},{"key":"e_1_2_8_78_1","doi-asserted-by":"publisher","DOI":"10.1039\/D3SC05627A"},{"key":"e_1_2_8_79_1","doi-asserted-by":"publisher","DOI":"10.1002\/chir.20108"},{"key":"e_1_2_8_80_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201305761"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202514676","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,18]],"date-time":"2025-10-18T17:14:07Z","timestamp":1760807647000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.202514676"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,9]]},"references-count":80,"journal-issue":{"issue":"43","published-print":{"date-parts":[[2025,10,20]]}},"alternative-id":["10.1002\/anie.202514676"],"URL":"https:\/\/doi.org\/10.1002\/anie.202514676","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,9]]},"assertion":[{"value":"2025-07-05","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-08-25","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-09-01","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202514676"}}