Host–Guest Recognition in the Crystalline State: Selective Inclusion of 1,4-Dibromobutane by Bromoethoxy-Functionalized Pillar[5]arenes

Host–Guest Recognition in the Crystalline State: Selective Inclusion of 1,4-Dibromobutane by Bromoethoxy-Functionalized Pillar[5]arenes | 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 Host–Guest Recognition in the Crystalline State: Selective Inclusion of 1,4-Dibromobutane by Bromoethoxy-Functionalized Pillar[5]arenes Mickey Vinodh, Fatemeh H. Alipour, Talal F. Al-Azemi This is a preprint; it has not been peer reviewed by a journal. https://doi.org/ 10.21203/rs.3.rs-6846598/v1 This work is licensed under a CC BY 4.0 License Status: Published Journal Publication published 11 Nov, 2025 Read the published version in Journal of Chemical Crystallography → Version 1 posted 9 You are reading this latest preprint version Abstract The guest encapsulation behavior and solid-state supramolecular assembly of four bromoethoxy-substituted pillar[5]arenes were investigated. These macrocycles selectively encapsulate 1,4-dibromobutane from equimolar mixtures of four α,ω-dibromoalkanes, forming 1:1 crystalline inclusion complexes. Single-crystal X-ray diffraction revealed that encapsulation is stabilized by C–H···π and C–H···O interactions within the macrocyclic cavity. The number and position of bromoethoxy groups significantly influence the supramolecular packing. While mono- and di-bromoethoxy-functionalized pillar[5]arenes exhibit only C–H···π and C–H···O interactions, the tetra- and hexa-bromoethoxy derivatives additionally display C–H···Br contacts, with the guest contributing to the assembly. Notably, the hexabromoethoxy-functionalized pillar[5]arene also exhibits Br···Br interactions, resulting in a distinct packing arrangement compared to the other systems. Bromo-pillararenes α ω-Dibromoalkanes Host-guest system Supramolecular polymer Hirshfeld surface analysis Full Text Additional Declarations No competing interests reported. Supplementary Files SupportinginformationJCCAlazemi.docx Cite Share Download PDF Status: Published Journal Publication published 11 Nov, 2025 Read the published version in Journal of Chemical Crystallography → Version 1 posted Editorial decision: Revision requested 11 Aug, 2025 Reviews received at journal 04 Aug, 2025 Reviewers agreed at journal 26 Jul, 2025 Reviews received at journal 25 Jul, 2025 Reviewers agreed at journal 23 Jul, 2025 Reviewers invited by journal 23 Jul, 2025 Editor assigned by journal 12 Jun, 2025 Submission checks completed at journal 12 Jun, 2025 First submitted to journal 08 Jun, 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. 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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-6846598","acceptedTermsAndConditions":true,"allowDirectSubmit":false,"archivedVersions":[],"articleType":"Research Article","associatedPublications":[],"authors":[{"id":489941596,"identity":"47045df9-541f-41e1-a155-1e61bf5ff8bb","order_by":0,"name":"Mickey Vinodh","email":"","orcid":"","institution":"Kuwait University","correspondingAuthor":false,"prefix":"","firstName":"Mickey","middleName":"","lastName":"Vinodh","suffix":""},{"id":489941600,"identity":"3722d0c5-3e1c-48a2-8483-8f7491fed12e","order_by":1,"name":"Fatemeh H. 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These macrocycles selectively encapsulate 1,4-dibromobutane from equimolar mixtures of four α,ω-dibromoalkanes, forming 1:1 crystalline inclusion complexes. Single-crystal X-ray diffraction revealed that encapsulation is stabilized by C\u0026ndash;H\u0026middot;\u0026middot;\u0026middot;π and C\u0026ndash;H\u0026middot;\u0026middot;\u0026middot;O interactions within the macrocyclic cavity. The number and position of bromoethoxy groups significantly influence the supramolecular packing. While mono- and di-bromoethoxy-functionalized pillar[5]arenes exhibit only C\u0026ndash;H\u0026middot;\u0026middot;\u0026middot;π and C\u0026ndash;H\u0026middot;\u0026middot;\u0026middot;O interactions, the tetra- and hexa-bromoethoxy derivatives additionally display C\u0026ndash;H\u0026middot;\u0026middot;\u0026middot;Br contacts, with the guest contributing to the assembly. Notably, the hexabromoethoxy-functionalized pillar[5]arene also exhibits Br\u0026middot;\u0026middot;\u0026middot;Br interactions, resulting in a distinct packing arrangement compared to the other systems.\u003c/p\u003e","manuscriptTitle":"Host–Guest Recognition in the Crystalline State: Selective Inclusion of 1,4-Dibromobutane by Bromoethoxy-Functionalized Pillar[5]arenes","msid":"","msnumber":"","nonDraftVersions":[{"code":1,"date":"2025-07-25 16:23:47","doi":"10.21203/rs.3.rs-6846598/v1","editorialEvents":[{"type":"communityComments","content":0},{"type":"decision","content":"Revision requested","date":"2025-08-11T19:59:54+00:00","index":"","fulltext":""},{"type":"editorInvitedReview","content":"","date":"2025-08-05T00:08:19+00:00","index":"hide","fulltext":""},{"type":"reviewerAgreed","content":"245018686690973122938712238109172649116","date":"2025-07-26T15:39:46+00:00","index":"hide","fulltext":""},{"type":"editorInvitedReview","content":"","date":"2025-07-25T12:04:38+00:00","index":"hide","fulltext":""},{"type":"reviewerAgreed","content":"67535649643421658344518071077495819204","date":"2025-07-23T19:00:34+00:00","index":"hide","fulltext":""},{"type":"reviewersInvited","content":"","date":"2025-07-23T18:42:57+00:00","index":"","fulltext":""},{"type":"editorAssigned","content":"","date":"2025-06-12T12:52:04+00:00","index":"","fulltext":""},{"type":"checksComplete","content":"","date":"2025-06-12T12:49:03+00:00","index":"","fulltext":""},{"type":"submitted","content":"Journal of Chemical Crystallography","date":"2025-06-08T09:15:39+00:00","index":"","fulltext":""}],"status":"published","journal":{"display":true,"email":"[email protected]","identity":"journal-of-chemical-crystallography","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":false,"externalIdentity":"jocc","sideBox":"Learn more about [Journal of Chemical Crystallography](http://link.springer.com/journal/10870)","snPcode":"10870","submissionUrl":"https://submission.nature.com/new-submission/10870/3","title":"Journal of Chemical Crystallography","twitterHandle":"","acdcEnabled":true,"dfaEnabled":true,"editorialSystem":"em","reportingPortfolio":"Springer Hybrid","inReviewEnabled":true,"inReviewRevisionsEnabled":false}}],"origin":"","ownerIdentity":"1be37534-c9d3-438a-9c70-71f06d2f429d","owner":[],"postedDate":"July 25th, 2025","published":true,"recentEditorialEvents":[],"rejectedJournal":[],"revision":"","amendment":"","status":"published-in-journal","subjectAreas":[],"tags":[],"updatedAt":"2025-11-17T16:01:54+00:00","versionOfRecord":{"articleIdentity":"rs-6846598","link":"https://doi.org/10.1007/s10870-025-01068-z","journal":{"identity":"journal-of-chemical-crystallography","isVorOnly":false,"title":"Journal of Chemical Crystallography"},"publishedOn":"2025-11-11 15:57:54","publishedOnDateReadable":"November 11th, 2025"},"versionCreatedAt":"2025-07-25 16:23:47","video":"","vorDoi":"10.1007/s10870-025-01068-z","vorDoiUrl":"https://doi.org/10.1007/s10870-025-01068-z","workflowStages":[]},"version":"v1","identity":"rs-6846598","journalConfig":"researchsquare"},"__N_SSP":true},"page":"/article/[identity]/[[...version]]","query":{"redirect":"/article/rs-6846598","identity":"rs-6846598","version":["v1"]},"buildId":"8U1c8b4HqxoKbykW_rLl7","isFallback":false,"isExperimentalCompile":false,"dynamicIds":[84888],"gssp":true,"scriptLoader":[]}