Dft Based Photophysical Assessment of Novel 2-substituted-3-pyridin-2-yl-benzo-[d][1,3]-azaphosphole P-oxide for Organic Optoelectronic Applications

Dft Based Photophysical Assessment of Novel 2-substituted-3-pyridin-2-yl-benzo-[d][1,3]-azaphosphole P-oxide for Organic Optoelectronic Applications | 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 Article Dft Based Photophysical Assessment of Novel 2-substituted-3-pyridin-2-yl-benzo-[d][1,3]-azaphosphole P-oxide for Organic Optoelectronic Applications Malik Muhammad Shoaib, Fatima Iftikhar, Tariq Mahmood, Khurshid Ayub, and 1 more This is a preprint; it has not been peer reviewed by a journal. https://doi.org/ 10.21203/rs.3.rs-8541791/v1 This work is licensed under a CC BY 4.0 License Status: Published Journal Publication published 22 Mar, 2026 Read the published version in Scientific Reports → Version 1 posted 13 You are reading this latest preprint version Abstract Phosphorus - containing heterocycles such as 1,3 - benzazaphospholes offer a tunable platform for emissive and charge - transport materials in organic electronics (OEs). Using DFT/TD - DFT at the B3LYP/6 - 31G(d,p) level, we design and evaluate nine novel donor - π - acceptor systems based on 2 - substituted - 3 - (pyridin - 2 - yl)benzo[d][1,3]azaphosphole 3 - oxide (PY-BAPO 1–9 ), with solvent (Chlorobenzene) and gas - phase analyses performed to isolate environmental effects. Targeted heteroacene Functionalization yields blue - emitting derivatives 7 – 9, which exhibit Photophysical properties ideal for blue OLEDs: tunable emission in the 440 – 510 nm (Blue/Blue-green) range, narrowed optical gaps (2.85 – 3.1 eV), high oscillator strengths ( f ≤ 0.625) and large Stokes shifts. Their exceptionally low hole reorganization energies (λ h = 0.20 – 0.36 eV) additionally suggest strong potential as hole - transport materials (HTMs) for OEs. These compounds also possess good stability, reflected in global hardness values of 1.6 – 1.9 eV and low total reorganization energies (0.6 – 0.9 eV). The strong nonlinear optical response, with hyperpolarizability up to 9.25 × 10 − 30 esu and favorable frontier orbital alignment further underscore their multifunctional potential. This work elucidates the superior role of the pyridine terminus over phenyl in enhancing charge transfer and provides clear design guidelines for stable, efficient blue - emitting and hole - transporting phosphorus - based semiconductors for next - generation OLEDs and organic photovoltaic’s. Physical sciences/Chemistry Physical sciences/Materials science Physical sciences/Optics and photonics Physical sciences/Physics Organophosphorus compounds Benzazaphosphole P-oxides Pyridine-based azaphosphole oxides Donor-π-acceptor systems Organic semiconductors Charge transport NLO and Hole mobility Full Text Additional Declarations No competing interests reported. Supplementary Files NOVEL2SUBSTITUTED3PYRIDIN2YLBENZOD13AZAPHOSPHOLEPOXIDEByShoaibsuppinfo.docx Cite Share Download PDF Status: Published Journal Publication published 22 Mar, 2026 Read the published version in Scientific Reports → Version 1 posted Editorial decision: Revision requested 20 Jan, 2026 Reviews received at journal 20 Jan, 2026 Reviews received at journal 17 Jan, 2026 Reviews received at journal 14 Jan, 2026 Reviewers agreed at journal 14 Jan, 2026 Reviewers agreed at journal 13 Jan, 2026 Reviewers agreed at journal 13 Jan, 2026 Reviewers agreed at journal 13 Jan, 2026 Reviewers invited by journal 13 Jan, 2026 Editor invited by journal 13 Jan, 2026 Editor assigned by journal 08 Jan, 2026 Submission checks completed at journal 08 Jan, 2026 First submitted to journal 07 Jan, 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. 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-8541791","acceptedTermsAndConditions":true,"allowDirectSubmit":false,"archivedVersions":[],"articleType":"Article","associatedPublications":[],"authors":[{"id":574860532,"identity":"7c587f93-e031-4222-b355-3f07fffbc42e","order_by":0,"name":"Malik Muhammad Shoaib","email":"","orcid":"","institution":"Hazara University","correspondingAuthor":false,"prefix":"","firstName":"Malik","middleName":"Muhammad","lastName":"Shoaib","suffix":""},{"id":574860535,"identity":"f683733e-ae5f-4b43-a172-a9634da8fd75","order_by":1,"name":"Fatima Iftikhar","email":"","orcid":"","institution":"Hazara 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Applications\u003c/p\u003e","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":"scientific-reports","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":false,"externalIdentity":"scirep","sideBox":"Learn more about [Scientific Reports](http://www.nature.com/srep/)","snPcode":"","submissionUrl":"","title":"Scientific Reports","twitterHandle":"","acdcEnabled":true,"dfaEnabled":true,"editorialSystem":"stoa","reportingPortfolio":"Scientific Reports","inReviewEnabled":true,"inReviewRevisionsEnabled":true},"keywords":"Organophosphorus compounds, Benzazaphosphole P-oxides, Pyridine-based azaphosphole oxides, Donor-π-acceptor systems, Organic semiconductors, Charge transport, NLO and Hole mobility","lastPublishedDoi":"10.21203/rs.3.rs-8541791/v1","lastPublishedDoiUrl":"https://doi.org/10.21203/rs.3.rs-8541791/v1","license":{"name":"CC BY 4.0","url":"https://creativecommons.org/licenses/by/4.0/"},"manuscriptAbstract":"\u003cp\u003ePhosphorus\u003cb\u003e-\u003c/b\u003econtaining heterocycles such as 1,3\u003cb\u003e-\u003c/b\u003ebenzazaphospholes offer a tunable platform for emissive and charge\u003cb\u003e-\u003c/b\u003etransport materials in organic electronics (OEs). Using DFT/TD\u003cb\u003e-\u003c/b\u003eDFT at the B3LYP/6\u003cb\u003e-\u003c/b\u003e31G(d,p) level, we design and evaluate nine novel donor\u003cb\u003e-\u003c/b\u003eπ\u003cb\u003e-\u003c/b\u003eacceptor systems based on 2\u003cb\u003e-\u003c/b\u003esubstituted\u003cb\u003e-\u003c/b\u003e3\u003cb\u003e-\u003c/b\u003e(pyridin\u003cb\u003e-\u003c/b\u003e2\u003cb\u003e-\u003c/b\u003eyl)benzo[d][1,3]azaphosphole 3\u003cb\u003e-\u003c/b\u003eoxide (PY-BAPO \u003cb\u003e1\u0026ndash;9\u003c/b\u003e), with solvent (Chlorobenzene) and gas\u003cb\u003e-\u003c/b\u003ephase analyses performed to isolate environmental effects. Targeted heteroacene Functionalization yields blue\u003cb\u003e-\u003c/b\u003eemitting derivatives 7\u003cb\u003e\u0026ndash;\u003c/b\u003e9, which exhibit Photophysical properties ideal for blue OLEDs: tunable emission in the 440\u003cb\u003e\u0026ndash;\u003c/b\u003e510 nm (Blue/Blue-green) range, narrowed optical gaps (2.85\u003cb\u003e\u0026ndash;\u003c/b\u003e3.1 eV), high oscillator strengths (\u003cem\u003ef\u003c/em\u003e\u0026thinsp;\u0026le;\u0026thinsp;0.625) and large Stokes shifts. Their exceptionally low hole reorganization energies (λ\u003csub\u003eh\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;0.20\u003cb\u003e\u0026ndash;\u003c/b\u003e0.36 eV) additionally suggest strong potential as hole\u003cb\u003e-\u003c/b\u003etransport materials (HTMs) for OEs. These compounds also possess good stability, reflected in global hardness values of 1.6\u003cb\u003e\u0026ndash;\u003c/b\u003e1.9 eV and low total reorganization energies (0.6\u003cb\u003e\u0026ndash;\u003c/b\u003e0.9 eV). The strong nonlinear optical response, with hyperpolarizability up to 9.25 \u0026times; 10\u003csup\u003e\u0026minus;\u0026thinsp;30\u003c/sup\u003e esu and favorable frontier orbital alignment further underscore their multifunctional potential. This work elucidates the superior role of the pyridine terminus over phenyl in enhancing charge transfer and provides clear design guidelines for stable, efficient blue\u003cb\u003e-\u003c/b\u003eemitting and hole\u003cb\u003e-\u003c/b\u003etransporting phosphorus\u003cb\u003e-\u003c/b\u003ebased semiconductors for next\u003cb\u003e-\u003c/b\u003egeneration OLEDs and organic photovoltaic\u0026rsquo;s.\u003c/p\u003e","manuscriptTitle":"Dft Based Photophysical Assessment of Novel 2-substituted-3-pyridin-2-yl-benzo-[d][1,3]-azaphosphole P-oxide for Organic Optoelectronic Applications","msid":"","msnumber":"","nonDraftVersions":[{"code":1,"date":"2026-01-16 03:59:05","doi":"10.21203/rs.3.rs-8541791/v1","editorialEvents":[{"type":"communityComments","content":0},{"type":"decision","content":"Revision requested","date":"2026-01-20T13:46:47+00:00","index":"","fulltext":""},{"type":"editorInvitedReview","content":"","date":"2026-01-20T05:03:20+00:00","index":"hide","fulltext":""},{"type":"editorInvitedReview","content":"","date":"2026-01-18T02:50:42+00:00","index":"hide","fulltext":""},{"type":"editorInvitedReview","content":"","date":"2026-01-15T03:14:13+00:00","index":"hide","fulltext":""},{"type":"reviewerAgreed","content":"71404652018700297146986399708408635742","date":"2026-01-14T12:34:16+00:00","index":"hide","fulltext":""},{"type":"reviewerAgreed","content":"123949425214812409631326373772020630648","date":"2026-01-13T15:10:07+00:00","index":"hide","fulltext":""},{"type":"reviewerAgreed","content":"200088555304651912557679920811627814449","date":"2026-01-13T13:12:07+00:00","index":"hide","fulltext":""},{"type":"reviewerAgreed","content":"174590364824714347518087338066029084613","date":"2026-01-13T12:54:07+00:00","index":"hide","fulltext":""},{"type":"reviewersInvited","content":"","date":"2026-01-13T12:46:13+00:00","index":"","fulltext":""},{"type":"editorInvited","content":"","date":"2026-01-13T09:26:03+00:00","index":"","fulltext":""},{"type":"editorAssigned","content":"","date":"2026-01-08T08:01:41+00:00","index":"","fulltext":""},{"type":"checksComplete","content":"","date":"2026-01-08T07:58:37+00:00","index":"","fulltext":""},{"type":"submitted","content":"Scientific Reports","date":"2026-01-07T12:46:20+00:00","index":"","fulltext":""}],"status":"published","journal":{"display":true,"email":"[email protected]","identity":"scientific-reports","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":false,"externalIdentity":"scirep","sideBox":"Learn more about [Scientific Reports](http://www.nature.com/srep/)","snPcode":"","submissionUrl":"","title":"Scientific Reports","twitterHandle":"","acdcEnabled":true,"dfaEnabled":true,"editorialSystem":"stoa","reportingPortfolio":"Scientific Reports","inReviewEnabled":true,"inReviewRevisionsEnabled":true}}],"origin":"","ownerIdentity":"54ed6634-ef9c-477a-86e6-3ce9010322c0","owner":[],"postedDate":"January 16th, 2026","published":true,"recentEditorialEvents":[],"rejectedJournal":[],"revision":"","amendment":"","status":"published-in-journal","subjectAreas":[{"id":61217546,"name":"Physical sciences/Chemistry"},{"id":61217547,"name":"Physical sciences/Materials science"},{"id":61217548,"name":"Physical sciences/Optics and photonics"},{"id":61217549,"name":"Physical sciences/Physics"}],"tags":[],"updatedAt":"2026-03-23T16:08:17+00:00","versionOfRecord":{"articleIdentity":"rs-8541791","link":"https://doi.org/10.1038/s41598-026-43447-2","journal":{"identity":"scientific-reports","isVorOnly":false,"title":"Scientific Reports"},"publishedOn":"2026-03-22 15:59:48","publishedOnDateReadable":"March 22nd, 2026"},"versionCreatedAt":"2026-01-16 03:59:05","video":"","vorDoi":"10.1038/s41598-026-43447-2","vorDoiUrl":"https://doi.org/10.1038/s41598-026-43447-2","workflowStages":[]},"version":"v1","identity":"rs-8541791","journalConfig":"researchsquare"},"__N_SSP":true},"page":"/article/[identity]/[[...version]]","query":{"redirect":"/article/rs-8541791","identity":"rs-8541791","version":["v1"]},"buildId":"XKTyCvWXoU3ODBz1xrDgd","isFallback":false,"isExperimentalCompile":false,"dynamicIds":[84888],"gssp":true,"scriptLoader":[]}