A Dual-Target Fluorescent Chemosensor Based on Naphthalene oxa-aza receptor for Zn²⁺ and Tyrosine Detection

A Dual-Target Fluorescent Chemosensor Based on Naphthalene oxa-aza receptor for Zn²⁺ and Tyrosine Detection | 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 A Dual-Target Fluorescent Chemosensor Based on Naphthalene oxa-aza receptor for Zn²⁺ and Tyrosine Detection Elham Koolivand, Reza Azadbakht, Hassan Keypour This is a preprint; it has not been peer reviewed by a journal. https://doi.org/ 10.21203/rs.3.rs-9377968/v1 This work is licensed under a CC BY 4.0 License Status: Under Review Version 1 posted 11 You are reading this latest preprint version Abstract In this study, a new dialdehyde was synthesized, followed by the successful preparation of a novel naphthalene-based oxa-aza receptor (L). The receptor was structurally characterized using a comprehensive suite of spectroscopic techniques, including UV–Vis, fluorescence, IR, ¹H NMR, ¹³C NMR, DEPT, HSQC, and mass spectrometry. The chemosensor demonstrated high selectivity and sensitivity toward Zn²⁺ ions and the amino acid tyrosine. Fluorescence titration revealed a marked enhancement in emission intensity upon Zn²⁺ coordination, with a 1:1 binding stoichiometry confirmed by Job’s plot and an association constant (K a ) determined via the Benesi–Hildebrand method. The detection limit for Zn²⁺ was calculated to be 1.86 × 10⁻ 8 M. Additionally, the chemosensor exhibited strong affinity for tyrosine, achieving a detection limit of 2.8 × 10⁻ 8 M. Fluorescence reversibility studies highlighted the excellent regeneration capability of the chemosensor, underscoring its potential as a reusable probe for biological and environmental monitoring applications. Chemosensor Dialdehyde Zinc ion Schiff base tyrosine Full Text Additional Declarations No competing interests reported. Supplementary Files SUpplementaryE.K.docx Cite Share Download PDF Status: Under Review Version 1 posted Editorial decision: Revision requested 08 May, 2026 Reviews received at journal 08 May, 2026 Reviewers agreed at journal 06 May, 2026 Reviewers agreed at journal 06 May, 2026 Reviews received at journal 05 May, 2026 Reviewers agreed at journal 22 Apr, 2026 Reviewers agreed at journal 21 Apr, 2026 Reviewers invited by journal 21 Apr, 2026 Editor assigned by journal 12 Apr, 2026 Submission checks completed at journal 12 Apr, 2026 First submitted to journal 10 Apr, 2026 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. 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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-9377968","acceptedTermsAndConditions":true,"allowDirectSubmit":false,"archivedVersions":[],"articleType":"Research Article","associatedPublications":[],"authors":[{"id":627737988,"identity":"7abb3c85-19f2-4b9d-98e7-b0c8775b21d2","order_by":0,"name":"Elham Koolivand","email":"","orcid":"","institution":"Bu-Ali Sina University","correspondingAuthor":false,"prefix":"","firstName":"Elham","middleName":"","lastName":"Koolivand","suffix":""},{"id":627737989,"identity":"1d75a2bf-4e03-4e42-98ea-a2465be024a7","order_by":1,"name":"Reza Azadbakht","email":"data:image/png;base64,iVBORw0KGgoAAAANSUhEUgAAAZAAAAAyAQMAAABI0h/eAAAABlBMVEX///8AAABVwtN+AAAACXBIWXMAAA7EAAAOxAGVKw4bAAAA20lEQVRIiWNgGAWjYNACtgMMEhIMjA8YGA6QpIWZ2YBkLWwSRGkxb2B+/OFH2R15ydn9x6p5au7I8TMwP3x0A48WmQNsBoY9554ZzpY5zHab59gzY8kGNmPjHDxagG4xSOBtO8w4TyIZqIXtcOKGAzxs0vi1sH84+LftsD1ISzHPP6K08Bg2A21JnA3UwgxiEKOlmFnm3LPkmTOSjSXn9h02lmwm6Bf2zR/flN2xnXEj8eGHN98Oy/GzNz98jE8Lg/wDBJuJB0Qy41OODhh/kKJ6FIyCUTAKRgwAAO3KS+pgJi08AAAAAElFTkSuQmCC","orcid":"","institution":"Bu-Ali Sina University","correspondingAuthor":true,"prefix":"","firstName":"Reza","middleName":"","lastName":"Azadbakht","suffix":""},{"id":627737990,"identity":"0e250a4f-4e69-4c16-b29e-9254a5100e39","order_by":2,"name":"Hassan Keypour","email":"","orcid":"","institution":"Bu-Ali Sina University","correspondingAuthor":false,"prefix":"","firstName":"Hassan","middleName":"","lastName":"Keypour","suffix":""}],"badges":[],"createdAt":"2026-04-10 10:08:09","currentVersionCode":1,"declarations":"","doi":"10.21203/rs.3.rs-9377968/v1","doiUrl":"https://doi.org/10.21203/rs.3.rs-9377968/v1","draftVersion":[],"editorialEvents":[],"editorialNote":"","failedWorkflow":false,"files":[{"id":108491018,"identity":"cf008f26-b5c7-4c71-a720-0dfea7e8d601","added_by":"auto","created_at":"2026-05-05 09:51:14","extension":"pdf","order_by":1,"title":"","display":"","copyAsset":false,"role":"manuscript-pdf","size":783338,"visible":true,"origin":"","legend":"","description":"","filename":"Kolivand1.pdf","url":"https://assets-eu.researchsquare.com/files/rs-9377968/v1_covered_c02da073-5b2e-4ddb-8502-5c8fcffa6e31.pdf"},{"id":108197769,"identity":"c7f70d2a-aea4-44f0-a571-2a422acdb6b4","added_by":"auto","created_at":"2026-04-30 11:17:17","extension":"docx","order_by":0,"title":"","display":"","copyAsset":false,"role":"supplement","size":7816354,"visible":true,"origin":"","legend":"","description":"","filename":"SUpplementaryE.K.docx","url":"https://assets-eu.researchsquare.com/files/rs-9377968/v1/26ff290ce08bf25cceeeb9d8.docx"}],"financialInterests":"No competing interests reported.","formattedTitle":"A Dual-Target Fluorescent Chemosensor Based on Naphthalene oxa-aza receptor for Zn²⁺ and Tyrosine Detection","fulltext":[],"fulltextSource":"","fullText":"","funders":[],"hasAdminPriorityOnWorkflow":false,"hasManuscriptDocX":false,"hasOptedInToPreprint":true,"hasPassedJournalQc":"","hasAnyPriority":false,"hideJournal":false,"highlight":"","institution":"","isAcceptedByJournal":true,"isAuthorSuppliedPdf":true,"isDeskRejected":"","isHiddenFromSearch":false,"isInQc":false,"isInWorkflow":false,"isPdf":true,"isPdfUpToDate":true,"isWithdrawnOrRetracted":false,"journal":{"display":true,"email":"[email protected]","identity":"journal-of-fluorescence","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":false,"externalIdentity":"jofl","sideBox":"Learn more about [Journal of Fluorescence](https://www.springer.com/journal/10895)","snPcode":"10895","submissionUrl":"https://submission.nature.com/new-submission/10895/3","title":"Journal of Fluorescence","twitterHandle":"","acdcEnabled":true,"dfaEnabled":true,"editorialSystem":"em","reportingPortfolio":"Springer Hybrid","inReviewEnabled":true,"inReviewRevisionsEnabled":false},"keywords":"Chemosensor, Dialdehyde, Zinc ion, Schiff base, tyrosine","lastPublishedDoi":"10.21203/rs.3.rs-9377968/v1","lastPublishedDoiUrl":"https://doi.org/10.21203/rs.3.rs-9377968/v1","license":{"name":"CC BY 4.0","url":"https://creativecommons.org/licenses/by/4.0/"},"manuscriptAbstract":"\u003cp\u003eIn this study, a new dialdehyde was synthesized, followed by the successful preparation of a novel naphthalene-based oxa-aza receptor (L). The receptor was structurally characterized using a comprehensive suite of spectroscopic techniques, including UV\u0026ndash;Vis, fluorescence, IR, \u0026sup1;H NMR, \u0026sup1;\u0026sup3;C NMR, DEPT, HSQC, and mass spectrometry. The chemosensor demonstrated high selectivity and sensitivity toward Zn\u0026sup2;⁺ ions and the amino acid tyrosine. Fluorescence titration revealed a marked enhancement in emission intensity upon Zn\u0026sup2;⁺ coordination, with a 1:1 binding stoichiometry confirmed by Job\u0026rsquo;s plot and an association constant (K\u003csub\u003ea\u003c/sub\u003e) determined via the Benesi\u0026ndash;Hildebrand method. The detection limit for Zn\u0026sup2;⁺ was calculated to be 1.86 \u0026times; 10⁻\u003csup\u003e8\u003c/sup\u003e M. Additionally, the chemosensor exhibited strong affinity for tyrosine, achieving a detection limit of 2.8 \u0026times; 10⁻\u003csup\u003e8\u003c/sup\u003e M. Fluorescence reversibility studies highlighted the excellent regeneration capability of the chemosensor, underscoring its potential as a reusable probe for biological and environmental monitoring applications.\u003c/p\u003e","manuscriptTitle":"A Dual-Target Fluorescent Chemosensor Based on Naphthalene oxa-aza receptor for Zn²⁺ and Tyrosine Detection","msid":"","msnumber":"","nonDraftVersions":[{"code":1,"date":"2026-04-30 11:17:08","doi":"10.21203/rs.3.rs-9377968/v1","editorialEvents":[{"type":"communityComments","content":0},{"type":"decision","content":"Revision requested","date":"2026-05-08T19:45:07+00:00","index":"","fulltext":""},{"type":"editorInvitedReview","content":"","date":"2026-05-08T15:29:53+00:00","index":"hide","fulltext":""},{"type":"reviewerAgreed","content":"79704705018452113562276456839577727807","date":"2026-05-07T00:40:24+00:00","index":"hide","fulltext":""},{"type":"reviewerAgreed","content":"69023416398863434046257323556634297399","date":"2026-05-06T18:02:46+00:00","index":"hide","fulltext":""},{"type":"editorInvitedReview","content":"","date":"2026-05-05T14:13:19+00:00","index":"hide","fulltext":""},{"type":"reviewerAgreed","content":"76678282823454917776411580938351398060","date":"2026-04-22T12:00:20+00:00","index":"hide","fulltext":""},{"type":"reviewerAgreed","content":"244628942827928434535889700207560954225","date":"2026-04-21T16:08:09+00:00","index":"hide","fulltext":""},{"type":"reviewersInvited","content":"","date":"2026-04-21T13:24:50+00:00","index":"","fulltext":""},{"type":"editorAssigned","content":"","date":"2026-04-13T03:18:40+00:00","index":"","fulltext":""},{"type":"checksComplete","content":"","date":"2026-04-13T03:17:45+00:00","index":"","fulltext":""},{"type":"submitted","content":"Journal of Fluorescence","date":"2026-04-10T09:50:31+00:00","index":"","fulltext":""}],"status":"published","journal":{"display":true,"email":"[email protected]","identity":"journal-of-fluorescence","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":false,"externalIdentity":"jofl","sideBox":"Learn more about [Journal of Fluorescence](https://www.springer.com/journal/10895)","snPcode":"10895","submissionUrl":"https://submission.nature.com/new-submission/10895/3","title":"Journal of Fluorescence","twitterHandle":"","acdcEnabled":true,"dfaEnabled":true,"editorialSystem":"em","reportingPortfolio":"Springer Hybrid","inReviewEnabled":true,"inReviewRevisionsEnabled":false}}],"origin":"","ownerIdentity":"36a6dfc8-6fad-49a9-ab85-6424f76078aa","owner":[],"postedDate":"April 30th, 2026","published":true,"recentEditorialEvents":[{"type":"decision","content":"Revision requested","date":"2026-05-08T19:45:07+00:00","index":"","fulltext":""},{"type":"editorInvitedReview","content":"","date":"2026-05-08T15:29:53+00:00","index":19,"fulltext":""},{"type":"reviewerAgreed","content":"79704705018452113562276456839577727807","date":"2026-05-07T00:40:24+00:00","index":18,"fulltext":""},{"type":"reviewerAgreed","content":"69023416398863434046257323556634297399","date":"2026-05-06T18:02:46+00:00","index":17,"fulltext":""},{"type":"editorInvitedReview","content":"","date":"2026-05-05T14:13:19+00:00","index":15,"fulltext":""}],"rejectedJournal":[],"revision":"","amendment":"","status":"under-review","subjectAreas":[],"tags":[],"updatedAt":"2026-05-19T00:23:59+00:00","versionOfRecord":[],"versionCreatedAt":"2026-04-30 11:17:08","video":"","vorDoi":"","vorDoiUrl":"","workflowStages":[]},"version":"v1","identity":"rs-9377968","journalConfig":"researchsquare"},"__N_SSP":true},"page":"/article/[identity]/[[...version]]","query":{"redirect":"/article/rs-9377968","identity":"rs-9377968","version":["v1"]},"buildId":"XKTyCvWXoU3ODBz1xrDgd","isFallback":false,"isExperimentalCompile":false,"dynamicIds":[84888],"gssp":true,"scriptLoader":[]}