Effective alternative host-guest separation strategies for mixed pyridine/methylpyridines with thioxanthenyl- and xanthenyl-derived host molecules

Effective alternative host-guest separation strategies for mixed pyridine/methylpyridines with thioxanthenyl- and xanthenyl-derived host molecules | Research Square window.SnipcartSettings = { analytics: { enabled: false } }; (function() { var accessVector = localStorage.getItem('access_vector') || ''; window.dataLayer = window.dataLayer || []; if (accessVector) { window.dataLayer.push({ user: { profile: { profileInfo: { snid: accessVector } } } }); } })(); (function(w,d,s,l,i){w[l]=w[l]||[];w[l].push({'gtm.start':new Date().getTime(),event:'gtm.js'});var f=d.getElementsByTagName(s)[0],j=d.createElement(s),dl=l!='dataLayer'?'&l='+l:'';j.async=true;j.src='https://www.googletagmanager.com/gtm.js?id='+i+dl;f.parentNode.insertBefore(j,f);})(window,document,'script','dataLayer','GTM-K279D39R'); Browse Preprints In Review Journals COVID-19 Preprints AJE Video Bytes Research Tools Research Promotion AJE Professional Editing AJE Rubriq About Preprint Platform In Review Editorial Policies Our Team Advisory Board Help Center Sign In Submit a Preprint Cite Share Download PDF Research Article Effective alternative host-guest separation strategies for mixed pyridine/methylpyridines with thioxanthenyl- and xanthenyl-derived host molecules Danica B Trollip, Benita Barton, Mino R Caira, Eric C Hosten This is a preprint; it has not been peer reviewed by a journal. https://doi.org/ 10.21203/rs.3.rs-7766700/v1 This work is licensed under a CC BY 4.0 License Status: Published Journal Publication published 19 Dec, 2025 Read the published version in Journal of Inclusion Phenomena and Macrocyclic Chemistry → Version 1 posted 12 You are reading this latest preprint version Abstract N , N’ -Bis(9-(4-fluorophenyl)-9-thioxanthenyl)ethylenediamine ( H1 ) and N , N ’-bis(9-(4-fluorophenyl)-9-xanthenyl)ethylenediamine ( H2 ) were demonstrated to have inclusion ability for pyridine (PYR) and the methylpyridine isomers (2MP, 3MP and 4MP); H:G ratios were 1:1 or 1:2. When guests competed, the host selectivities were observed to be in the order 4MP > 3MP > 2MP > > PYR ( H1 ) and PYR > 4MP > 2MP > > 3MP ( H2 ) and so substitution of the sulfur atom for oxygen in the central B ring of the host compound resulted in significant changes in the host selectivity behaviour. Furthermore, H1 was shown to have the ability to separate the 80:20 4MP/PYR solution (K = infinite, in favour of 4MP), while H2 was even more effective, able to separate numerous of the binary mixtures employed here. (These guests do present as mixtures in the chemical industry, which are difficult to separate through fractional distillations owing to comparable boiling points). Thermal experiments demonstrated that H1 ·4MP (4MP being preferred by H1 ) was thermally more stable than the other three complexes; H1 ·PYR (least favoured guest) was unstable even at ambient conditions. The affinity behaviour of H2 , however, could not be as readily explained through thermal analyses. SCXRD analyses showed numerous noncovalent interactions present in all eight complexes, including a classical (host)N‒H···N(guest) hydrogen bond to each guest molecule (except 2MP in H1 ·2MP), which assisted in retention of the guest within the crystals of each complex. Supramolecular Host-guest Separation Methylpyridine Selectivity Full Text Additional Declarations No competing interests reported. Supplementary Files SIFINAL.docx Cite Share Download PDF Status: Published Journal Publication published 19 Dec, 2025 Read the published version in Journal of Inclusion Phenomena and Macrocyclic Chemistry → Version 1 posted Editorial decision: Revision requested 13 Nov, 2025 Reviews received at journal 12 Nov, 2025 Reviews received at journal 03 Nov, 2025 Reviewers agreed at journal 30 Oct, 2025 Reviewers agreed at journal 30 Oct, 2025 Reviews received at journal 18 Oct, 2025 Reviewers agreed at journal 04 Oct, 2025 Reviewers agreed at journal 04 Oct, 2025 Reviewers invited by journal 02 Oct, 2025 Editor assigned by journal 02 Oct, 2025 Submission checks completed at journal 02 Oct, 2025 First submitted to journal 02 Oct, 2025 You are reading this latest preprint version Research Square lets you share your work early, gain feedback from the community, and start making changes to your manuscript prior to peer review in a journal. As a division of Research Square Company, we’re committed to making research communication faster, fairer, and more useful. We do this by developing innovative software and high quality services for the global research community. Our growing team is made up of researchers and industry professionals working together to solve the most critical problems facing scientific publishing. Also discoverable on Platform About Our Team In Review Editorial Policies Advisory Board Help Center Resources Author Services Accessibility API Access RSS feed Manage Cookie Preferences © Research Square 2026 | ISSN 2693-5015 (online) Privacy Policy Terms of Service Do Not Sell My Personal Information {"props":{"pageProps":{"initialData":{"identity":"rs-7766700","acceptedTermsAndConditions":true,"allowDirectSubmit":false,"archivedVersions":[],"articleType":"Research Article","associatedPublications":[],"authors":[{"id":528368604,"identity":"d24344c0-629b-469a-a4c9-75cc1352da4a","order_by":0,"name":"Danica B Trollip","email":"","orcid":"","institution":"Nelson Mandela University","correspondingAuthor":false,"prefix":"","firstName":"Danica","middleName":"B","lastName":"Trollip","suffix":""},{"id":528368605,"identity":"9b895113-0182-4a32-a3f3-ed155d86600c","order_by":1,"name":"Benita 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Chemistry","twitterHandle":"","acdcEnabled":true,"dfaEnabled":true,"editorialSystem":"em","reportingPortfolio":"Springer Hybrid","inReviewEnabled":true,"inReviewRevisionsEnabled":false},"keywords":"Supramolecular, Host-guest, Separation, Methylpyridine, Selectivity","lastPublishedDoi":"10.21203/rs.3.rs-7766700/v1","lastPublishedDoiUrl":"https://doi.org/10.21203/rs.3.rs-7766700/v1","license":{"name":"CC BY 4.0","url":"https://creativecommons.org/licenses/by/4.0/"},"manuscriptAbstract":"\u003cp\u003e\u003cem\u003eN\u003c/em\u003e,\u003cem\u003eN\u0026rsquo;\u003c/em\u003e-Bis(9-(4-fluorophenyl)-9-thioxanthenyl)ethylenediamine (\u003cb\u003eH1\u003c/b\u003e) and \u003cem\u003eN\u003c/em\u003e,\u003cem\u003eN\u003c/em\u003e\u0026rsquo;-bis(9-(4-fluorophenyl)-9-xanthenyl)ethylenediamine (\u003cb\u003eH2\u003c/b\u003e) were demonstrated to have inclusion ability for pyridine (PYR) and the methylpyridine isomers (2MP, 3MP and 4MP); H:G ratios were 1:1 or 1:2. When guests competed, the host selectivities were observed to be in the order 4MP\u0026thinsp;\u0026gt;\u0026thinsp;3MP\u0026thinsp;\u0026gt;\u0026thinsp;2MP\u0026thinsp;\u0026gt;\u0026thinsp;\u0026gt;\u0026thinsp;PYR (\u003cb\u003eH1\u003c/b\u003e) and PYR\u0026thinsp;\u0026gt;\u0026thinsp;4MP\u0026thinsp;\u0026gt;\u0026thinsp;2MP\u0026thinsp;\u0026gt;\u0026thinsp;\u0026gt;\u0026thinsp;3MP (\u003cb\u003eH2\u003c/b\u003e) and so substitution of the sulfur atom for oxygen in the central B ring of the host compound resulted in significant changes in the host selectivity behaviour. Furthermore, \u003cb\u003eH1\u003c/b\u003e was shown to have the ability to separate the 80:20 4MP/PYR solution (K\u0026thinsp;=\u0026thinsp;infinite, in favour of 4MP), while \u003cb\u003eH2\u003c/b\u003e was even more effective, able to separate numerous of the binary mixtures employed here. (These guests do present as mixtures in the chemical industry, which are difficult to separate through fractional distillations owing to comparable boiling points). Thermal experiments demonstrated that \u003cb\u003eH1\u003c/b\u003e\u0026middot;4MP (4MP being preferred by \u003cb\u003eH1\u003c/b\u003e) was thermally more stable than the other three complexes; \u003cb\u003eH1\u003c/b\u003e\u0026middot;PYR (least favoured guest) was unstable even at ambient conditions. The affinity behaviour of \u003cb\u003eH2\u003c/b\u003e, however, could not be as readily explained through thermal analyses. SCXRD analyses showed numerous noncovalent interactions present in all eight complexes, including a classical (host)N‒H\u0026middot;\u0026middot;\u0026middot;N(guest) hydrogen bond to each guest molecule (except 2MP in \u003cb\u003eH1\u003c/b\u003e\u0026middot;2MP), which assisted in retention of the guest within the crystals of each complex.\u003c/p\u003e","manuscriptTitle":"Effective alternative host-guest separation strategies for mixed pyridine/methylpyridines with thioxanthenyl- and xanthenyl-derived host molecules","msid":"","msnumber":"","nonDraftVersions":[{"code":1,"date":"2025-10-15 23:11:19","doi":"10.21203/rs.3.rs-7766700/v1","editorialEvents":[{"type":"communityComments","content":0},{"type":"decision","content":"Revision requested","date":"2025-11-13T06:59:56+00:00","index":"","fulltext":""},{"type":"editorInvitedReview","content":"","date":"2025-11-13T04:46:54+00:00","index":"hide","fulltext":""},{"type":"editorInvitedReview","content":"","date":"2025-11-03T13:42:09+00:00","index":"hide","fulltext":""},{"type":"reviewerAgreed","content":"52695984855840478138711941956064237270","date":"2025-10-31T00:10:34+00:00","index":"hide","fulltext":""},{"type":"reviewerAgreed","content":"162862726558177847268051331179533483826","date":"2025-10-30T11:02:51+00:00","index":"hide","fulltext":""},{"type":"editorInvitedReview","content":"","date":"2025-10-18T23:05:57+00:00","index":"hide","fulltext":""},{"type":"reviewerAgreed","content":"35261219757350533317460955974842543962","date":"2025-10-04T23:22:12+00:00","index":"hide","fulltext":""},{"type":"reviewerAgreed","content":"263857478762167161705234503982604881267","date":"2025-10-04T15:54:32+00:00","index":"hide","fulltext":""},{"type":"reviewersInvited","content":"","date":"2025-10-02T15:38:15+00:00","index":"","fulltext":""},{"type":"editorAssigned","content":"","date":"2025-10-02T14:55:03+00:00","index":"","fulltext":""},{"type":"checksComplete","content":"","date":"2025-10-02T14:54:50+00:00","index":"","fulltext":""},{"type":"submitted","content":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","date":"2025-10-02T13:01:03+00:00","index":"","fulltext":""}],"status":"published","journal":{"display":true,"email":"[email protected]","identity":"journal-of-inclusion-phenomena-and-macrocyclic-chemistry","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":false,"externalIdentity":"jiph","sideBox":"Learn more about [Journal of Inclusion Phenomena and Macrocyclic Chemistry](http://link.springer.com/journal/10847)","snPcode":"10847","submissionUrl":"https://submission.nature.com/new-submission/10847/3","title":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","twitterHandle":"","acdcEnabled":true,"dfaEnabled":true,"editorialSystem":"em","reportingPortfolio":"Springer Hybrid","inReviewEnabled":true,"inReviewRevisionsEnabled":false}}],"origin":"","ownerIdentity":"607a68dd-dced-4809-9ce2-e7bc472f2977","owner":[],"postedDate":"October 15th, 2025","published":true,"recentEditorialEvents":[],"rejectedJournal":[],"revision":"","amendment":"","status":"published-in-journal","subjectAreas":[],"tags":[],"updatedAt":"2025-12-22T16:03:23+00:00","versionOfRecord":{"articleIdentity":"rs-7766700","link":"https://doi.org/10.1007/s10847-025-01324-x","journal":{"identity":"journal-of-inclusion-phenomena-and-macrocyclic-chemistry","isVorOnly":false,"title":"Journal of Inclusion Phenomena and Macrocyclic Chemistry"},"publishedOn":"2025-12-19 15:58:35","publishedOnDateReadable":"December 19th, 2025"},"versionCreatedAt":"2025-10-15 23:11:19","video":"","vorDoi":"10.1007/s10847-025-01324-x","vorDoiUrl":"https://doi.org/10.1007/s10847-025-01324-x","workflowStages":[]},"version":"v1","identity":"rs-7766700","journalConfig":"researchsquare"},"__N_SSP":true},"page":"/article/[identity]/[[...version]]","query":{"redirect":"/article/rs-7766700","identity":"rs-7766700","version":["v1"]},"buildId":"8U1c8b4HqxoKbykW_rLl7","isFallback":false,"isExperimentalCompile":false,"dynamicIds":[84888],"gssp":true,"scriptLoader":[]}