{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,21]],"date-time":"2026-09-21T18:14:22Z","timestamp":1790014462002,"version":"4.0.1"},"reference-count":50,"publisher":"American Chemical Society (ACS)","issue":"30","license":[{"start":{"date-parts":[[2026,7,23]],"date-time":"2026-07-23T00:00:00Z","timestamp":1784764800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2026,7,23]],"date-time":"2026-07-23T00:00:00Z","timestamp":1784764800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2026,7,23]],"date-time":"2026-07-23T00:00:00Z","timestamp":1784764800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-045"}],"funder":[{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["22371241"],"award-info":[{"award-number":["22371241"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["22541160267"],"award-info":[{"award-number":["22541160267"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"name":"North Sichuan Medical College","award":["CBY23-QDA15"],"award-info":[{"award-number":["CBY23-QDA15"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,8,5]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Conformational chirality is widespread in principle, yet often inaccessible in practice because rapid stereochemical averaging can preclude both enantiomeric resolution and chiroptical characterization. Here we show that a stereolabile pillar[5]arene-based macrocycle, though dynamically racemic in solution, undergoes spontaneous resolution upon crystallization to form a conglomerate. Single-crystal X-ray diffraction shows that individual crystals contain one of the two enantiomeric conformers, while solid-state electronic and vibrational circular dichroism, supported by density functional theory calculations, establish their absolute configurations. Notably, this handedness is also expressed in distinguishable hemihedral facets, enabling manual sorting by external morphology. The same conglomerate packing motif can be retained across related solvomorphs, while a chiral guest can bias crystallization toward a single-handed form. These results establish a direct link among molecular structure, solid-state chiroptical response, crystal morphology, and absolute configuration within a dynamically racemic system, and illustrate how crystallization can render otherwise averaged conformational chirality structurally, spectroscopically, and even visually legible.<\/jats:p>","DOI":"10.1021\/jacs.6c10931","type":"journal-article","created":{"date-parts":[[2026,7,23]],"date-time":"2026-07-23T06:53:01Z","timestamp":1784789581000},"page":"32736-32742","source":"Crossref","is-referenced-by-count":2,"title":["Resolving Conformational\nChirality in a Stereolabile\nMacrocycle"],"prefix":"10.1021","volume":"148","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-4728-607X","authenticated-orcid":true,"given":"Haiying","family":"Wang","sequence":"first","affiliation":[{"name":"Xiamen University , , , ,","place":["Xiamen, Fujian, P. R. China, 61005"]},{"name":"North Sichuan Medical College , , , ,","place":["Nanchong, Sichuan, China, 637000"]},{"name":"Tianjin University , , ,","place":["Tianjin, China, 300072"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3612-9493","authenticated-orcid":true,"given":"Cai-Hong","family":"Zhan","sequence":"additional","affiliation":[{"name":"Zhejiang Normal University , , , ,","place":["Jinhua, Zhejiang, China, 321004"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7171-3487","authenticated-orcid":true,"given":"Kim K.","family":"Baldridge","sequence":"additional","affiliation":[{"name":"Tianjin University , , ,","place":["Tianjin, China, 300072"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yinan","family":"Lu","sequence":"additional","affiliation":[{"name":"Xiamen University , , , ,","place":["Xiamen, Fujian, P. R. China, 61005"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Li-Rong","family":"Lin","sequence":"additional","affiliation":[{"name":"Xiamen University , , , ,","place":["Xiamen, Fujian, P. R. China, 61005"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8192-1116","authenticated-orcid":true,"given":"Hui","family":"Zhang","sequence":"additional","affiliation":[{"name":"Xiamen University , , , ,","place":["Xiamen, Fujian, P. R. China, 61005"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9557-2658","authenticated-orcid":true,"given":"Andrew C.-H.","family":"Sue","sequence":"additional","affiliation":[{"name":"Xiamen University , , , ,","place":["Xiamen, Fujian, P. R. China, 61005"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,7,23]]},"reference":[{"key":"2026080511122902900_cit1","doi-asserted-by":"crossref","DOI":"10.1007\/978-3-030-84961-0","volume-title":"Stereochemistry of\nOrganic Compounds","author":"Ahluwalia","year":"2022"},{"key":"2026080511122902900_cit2","volume-title":"Enantiomers Racemates\nand Resolutions","author":"Jacques","year":"1981"},{"key":"2026080511122902900_cit3","doi-asserted-by":"publisher","first-page":"342","DOI":"10.1039\/B201099M","article-title":"Spontaneous Resolution Under Supramolecular Control","volume":"31","author":"Pe\u0301rez-Garci\u0301a","year":"2002","journal-title":"Chem. Soc. Rev."},{"key":"2026080511122902900_cit4","doi-asserted-by":"publisher","first-page":"941","DOI":"10.1039\/B610714A","article-title":"Spontaneous Resolution, Whence and Whither: From Enantiomorphic\nSolids to Chiral Liquid Crystals, Monolayers and Macro- and Supra-Molecular\nPolymers and Assemblies","volume":"36","author":"Pe\u0301rez-Garci\u0301a","year":"2007","journal-title":"Chem. Soc. Rev."},{"key":"2026080511122902900_cit5","doi-asserted-by":"publisher","first-page":"269","DOI":"10.1002\/(SICI)1520-636X(2000)12:4&lt;269::AID-CHIR13&gt;3.0.CO;2-P","article-title":"CD Spectra of Solid-State\nSamples","volume":"12","author":"Kuroda","year":"2000","journal-title":"Chirality"},{"key":"2026080511122902900_cit6","doi-asserted-by":"publisher","first-page":"1781","DOI":"10.1039\/c1nj20185a","article-title":"Concentration\nEffects in Solid-State CD Spectra of Chiral Atropisomeric Compounds","volume":"35","author":"Ding","year":"2011","journal-title":"New J. Chem."},{"key":"2026080511122902900_cit7","doi-asserted-by":"publisher","first-page":"1067","DOI":"10.1021\/cg401577m","article-title":"Viedma\nRipening of Conglomerate Crystals of Achiral Molecules Monitored Using\nSolid-State Circular Dichroism","volume":"14","author":"McLaughlin","year":"2014","journal-title":"Cryst. Growth\nDes."},{"key":"2026080511122902900_cit8","doi-asserted-by":"publisher","first-page":"670","DOI":"10.1039\/b008379h","article-title":"Circular Dichroism\nStudies of Crystalline Chiral and Achiral \u03b1-Nitronyl Nitroxide\nRadicals in a KBr Matrix","volume":"30","author":"Minguet","year":"2001","journal-title":"J. Chem. Soc., Perkin\nTrans. 2"},{"key":"2026080511122902900_cit9","doi-asserted-by":"publisher","first-page":"173","DOI":"10.1016\/0022-0248(93)90849-R","article-title":"Recognition of Enantiomers\nThrough Morphology of Single\nCrystals; Application to Some 5-Alkyl-5-Aryl-Hydantoin Derivatives","volume":"130","author":"Coquerel","year":"1993","journal-title":"J. Cryst. Growth"},{"key":"2026080511122902900_cit10","doi-asserted-by":"publisher","first-page":"777","DOI":"10.1021\/ed052p777","article-title":"The Resolution of Racemic Acid: A\nClassic Stereochemical\nExperiment for the Undergraduate Laboratory","volume":"52","author":"Kauffman","year":"1975","journal-title":"J. Chem. 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Rev."},{"key":"2026080511122902900_cit16","doi-asserted-by":"publisher","first-page":"1198","DOI":"10.1039\/B404388J","article-title":"\u201cInherent\nChirality\u201d and Curvature","volume":"28","author":"Dalla Cort","year":"2004","journal-title":"New J. Chem."},{"key":"2026080511122902900_cit17","doi-asserted-by":"publisher","first-page":"1278","DOI":"10.1246\/cl.190544","article-title":"Conformation and Planar\nChirality of Pillar[n]arenes","volume":"48","author":"Fa","year":"2019","journal-title":"Chem. Lett."},{"key":"2026080511122902900_cit18","doi-asserted-by":"publisher","first-page":"9029","DOI":"10.1039\/D1CC03778A","article-title":"Pillararenes:\nFascinating Planar\nChiral Macrocyclic Arenes","volume":"57","author":"Chen","year":"2021","journal-title":"Chem. 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Lett."},{"key":"2026080511122902900_cit22","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202415190","article-title":"Catalytic\nEnantioselective Synthesis of Planar Chiral Pillar[5]arenes via Asymmetric\nSonogashira Coupling","volume":"64","author":"Zhou","year":"2025","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026080511122902900_cit23","doi-asserted-by":"publisher","first-page":"7493","DOI":"10.1002\/chem.201200122","article-title":"High-Yield Diastereoselective\nSynthesis\nof Planar Chiral [2]- and [3]-Rotaxanes Constructed from Per-Ethylated\nPillar[5]arene and Pyridinium Derivatives","volume":"18","author":"Ogoshi","year":"2012","journal-title":"Chem.\n- Eur. J."},{"key":"2026080511122902900_cit24","doi-asserted-by":"publisher","first-page":"7590","DOI":"10.1038\/ncomms8590","article-title":"Mechanically Selflocked\nChiral Gemini Catenanes","volume":"6","author":"Li","year":"2015","journal-title":"Nat. Commun."},{"key":"2026080511122902900_cit25","doi-asserted-by":"publisher","first-page":"3648","DOI":"10.1039\/D2CS00169A","article-title":"Noncovalently\nBound and Mechanically Interlocked Systems Using Pillar[n]arenes","volume":"51","author":"Kato","year":"2022","journal-title":"Chem. Soc. Rev."},{"key":"2026080511122902900_cit26","doi-asserted-by":"publisher","first-page":"17436","DOI":"10.1021\/ja3082523","article-title":"Incorporation of\nan A1\/A2-Difunctionalized Pillar[5]arene into a Metal\u2013Organic\nFramework","volume":"134","author":"Strutt","year":"2012","journal-title":"J. Am. Chem. Soc."},{"key":"2026080511122902900_cit27","doi-asserted-by":"publisher","first-page":"9876","DOI":"10.1039\/c2cc35498e","article-title":"Syntheses of a Pillar[4]arene[1]quinone\nand a Difunctionalized Pillar[5]arene by Partial Oxidation","volume":"48","author":"Han","year":"2012","journal-title":"Chem. Commun."},{"key":"2026080511122902900_cit28","doi-asserted-by":"publisher","first-page":"10","DOI":"10.1039\/C7QO00641A","article-title":"A New Approach for\nthe Synthesis of Mono- and A1\/A2-Dihydroxy-Substituted Pillar[5]arenes\nand Their Complexation with Alkyl Alcohols in Solution and in the\nSolid State","volume":"5","author":"Al-Azemi","year":"2018","journal-title":"Org. Chem. Front."},{"key":"2026080511122902900_cit29","doi-asserted-by":"publisher","first-page":"10985","DOI":"10.1039\/D1SC02560K","article-title":"Spontaneous and\nInduced Chiral Symmetry Breaking of\nStereolabile Pillar[5]arene Derivatives Upon Crystallization","volume":"12","author":"Wang","year":"2021","journal-title":"Chem. Sci."},{"key":"2026080511122902900_cit30","doi-asserted-by":"publisher","first-page":"6185","DOI":"10.1002\/chem.201600688","article-title":"Piling\nUp Pillar[5]arenes to Self-Assemble Nanotubes","volume":"22","author":"Nierengarten","year":"2016","journal-title":"Chem. - Eur. J."},{"key":"2026080511122902900_cit31","doi-asserted-by":"publisher","first-page":"7007","DOI":"10.1039\/c1ob05871a","article-title":"Efficient\nSynthesis of Copillar[5]arenes and Their Host\u2013Guest Properties\nwith Dibromoalkanes","volume":"9","author":"Liu","year":"2011","journal-title":"Org. Biomol. Chem."},{"key":"2026080511122902900_cit32","doi-asserted-by":"publisher","first-page":"11892","DOI":"10.1002\/chem.201301022","article-title":"Supramolecular\nPolymers Based on Efficient Pillar[5]arene\u2500Neutral\nGuest Motifs","volume":"19","author":"Li","year":"2013","journal-title":"Chem. - Eur. J."},{"key":"2026080511122902900_cit33","doi-asserted-by":"publisher","first-page":"3260","DOI":"10.1021\/acs.orglett.5b01418","article-title":"Activation-Enabled\nSyntheses of Functionalized Pillar[5]arene\nDerivatives","volume":"17","author":"Han","year":"2015","journal-title":"Org. Lett."},{"key":"2026080511122902900_cit34","doi-asserted-by":"publisher","first-page":"7423","DOI":"10.1021\/acs.orglett.1c02620","article-title":"Redox-Driven\nChiral Inversion of Water-Soluble Pillar[5]arene\nwith L-Cystine Derivative in the Aqueous Medium","volume":"23","author":"Chen","year":"2021","journal-title":"Org. Lett."},{"key":"2026080511122902900_cit35","doi-asserted-by":"publisher","first-page":"590","DOI":"10.1038\/s41467-023-36131-w","article-title":"Cation Controlled Rotation in Anionic Pillar[5]arenes and Its Application\nfor Fluorescence Switch","volume":"14","author":"Zheng","year":"2023","journal-title":"Nat. Commun."},{"key":"2026080511122902900_cit36","doi-asserted-by":"publisher","first-page":"618","DOI":"10.1021\/jo1021508","article-title":"Planar-Chiral Pillar[5]arene:\nChiral Switches Induced by Multiexternal Stimulus of Temperature,\nSolvents, and Addition of Achiral Guest Molecule","volume":"76","author":"Ogoshi","year":"2011","journal-title":"J. Org. Chem."},{"key":"2026080511122902900_cit37","doi-asserted-by":"publisher","first-page":"8424","DOI":"10.1039\/D0CC03413D","article-title":"Holding of\nPlanar Chirality of Pillar[5]arene by Kinetic Trapping Using Host\u2013Guest\nInteractions with Achiral Guest Solvents","volume":"56","author":"Nagata","year":"2020","journal-title":"Chem.\nCommun."},{"key":"2026080511122902900_cit38","doi-asserted-by":"publisher","first-page":"8114","DOI":"10.1021\/jacs.3c01019","article-title":"Adaptive Planar Chirality of Pillar[5]arenes\nInvertible by n-Alkane Lengths","volume":"145","author":"Adachi","year":"2023","journal-title":"J. Am. Chem. Soc."},{"key":"2026080511122902900_cit39","doi-asserted-by":"publisher","first-page":"1232","DOI":"10.1021\/acs.orglett.9b00277","article-title":"Critical Role of\nAchiral Guest Molecules in Planar Chirality Inversion of Alanine-Appended\nPillar[5]arenes","volume":"21","author":"Park","year":"2019","journal-title":"Org. Lett."},{"key":"2026080511122902900_cit40","doi-asserted-by":"publisher","first-page":"10868","DOI":"10.1002\/anie.202001680","article-title":"Pillararene\nHost\u2013Guest Complexation Induced Chirality Amplification: A\nNew Way to Detect Cryptochiral Compounds","volume":"59","author":"Zhu","year":"2020","journal-title":"Angew.\nChem., Int. Ed."},{"key":"2026080511122902900_cit41","doi-asserted-by":"publisher","first-page":"74","DOI":"10.1021\/jacs.7b10767","article-title":"Rim-Differentiated C5-Symmetric Tiara-Pillar[5]arenes","volume":"140","author":"Guo","year":"2018","journal-title":"J. Am. Chem. Soc."},{"key":"2026080511122902900_cit42","doi-asserted-by":"publisher","first-page":"5874","DOI":"10.1039\/c2cc17727g","article-title":"On the Abundance of Chiral Crystals","volume":"48","author":"Dryzun","year":"2012","journal-title":"Chem.\nCommun."},{"key":"2026080511122902900_cit43","doi-asserted-by":"publisher","DOI":"10.1002\/978111997651","volume-title":"Vibrational Optical\nActivity: principles and Applications","author":"Nafie","year":"2011"},{"key":"2026080511122902900_cit44","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202215599","article-title":"How Crystal\nSymmetry Dictates Non-Local Vibrational\nCircular Dichroism in the Solid State","volume":"62","author":"Ja\u0308hnigen","year":"2023","journal-title":"Angew.\nChem., Int. Ed."},{"key":"2026080511122902900_cit45","first-page":"535","article-title":"Me\u0301moire\nsur la Relation Qui Peut Exister Entre la Forme Cristalline et la\nComposition Chimique, et sur la Cause de la Polarisation Rotatoire","volume":"26","author":"Pasteur","year":"1848","journal-title":"Compt. Rend."},{"key":"2026080511122902900_cit46","first-page":"442","article-title":"Sur Les Relations\nQui Peuvent Exister Entre la Forme Cristalline, la Composition Chimique\net le Sens de la Polarisation Rotatoire","volume":"24","author":"Pasteur","year":"1848","journal-title":"Anal.\nChim. Phys."},{"key":"2026080511122902900_cit47","doi-asserted-by":"publisher","first-page":"371","DOI":"10.1107\/S0108767309024088","article-title":"Louis Pasteur\u2019s\nDiscovery of Molecular Chirality and Spontaneous Resolution in 1848,\nTogether with a Complete Review of His Crystallographic and Chemical\nWork","volume":"A65","author":"Flack","year":"2009","journal-title":"Acta Crystallogr."},{"key":"2026080511122902900_cit48","doi-asserted-by":"publisher","first-page":"93","DOI":"10.1070\/MC2003v013n03ABEH001803","article-title":"The Reexamination\nof Pasteur\u2019s Experiment in Japan","volume":"13","author":"Tobe","year":"2003","journal-title":"Mendeleev\nCommun."},{"key":"2026080511122902900_cit49","first-page":"955","article-title":"Morphology\nof Sodium Ammonium Tartrate: Pasteur\u2019s Spontaneous Resolution\nand Its Reexamination","volume":"33","author":"Nakazaki","year":"1979","journal-title":"Kagaku No Ryoiki"},{"key":"2026080511122902900_cit50","unstructured":"Sivakumar, R.\n          \n          The Role\nof Conglomerate\nCrystallization in Spontaneous Resolution and Chiral Amplification, Masters Thesis, Concordia University, 2016."}],"container-title":["Journal of the American\nChemical Society"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/jacs.6c10931","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/jacsat\/article-pdf\/148\/30\/32736\/66200214\/jacs.6c10931.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/jacsat\/article-pdf\/148\/30\/32736\/66200214\/jacs.6c10931.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,8,5]],"date-time":"2026-08-05T15:23:56Z","timestamp":1785943436000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/jacsat\/article\/148\/30\/32736\/5229475\/Resolving-Conformational-Chirality-in-a"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,7,23]]},"references-count":50,"journal-issue":{"issue":"30","published-online":{"date-parts":[[2026,7,23]]},"published-print":{"date-parts":[[2026,8,5]]}},"URL":"https:\/\/doi.org\/10.1021\/jacs.6c10931","relation":{},"ISSN":["0002-7863","1520-5126"],"issn-type":[{"value":"0002-7863","type":"print"},{"value":"1520-5126","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,7,23]]}}}