Substrate-affinitive azapolycyclic photosensitizer for direct nitrilization of primary amides

Substrate-affinitive azapolycyclic photosensitizer for direct nitrilization of primary amides | 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 Substrate-affinitive azapolycyclic photosensitizer for direct nitrilization of primary amides Jinwoo Kim, Seongwoo Bae, Dongwook Kim This is a preprint; it has not been peer reviewed by a journal. https://doi.org/ 10.21203/rs.3.rs-7770848/v1 This work is licensed under a CC BY 4.0 License Status: Posted Version 1 posted You are reading this latest preprint version Abstract Herein we report azapolycyclic quinoxalinoquinoxaline (QQ) photosensitizers that promote light-driven nitrilization of primary amides under mild conditions. The QQ scaffold, designed to combine strong excited-state reduction potential with hydrogen-bonding capacity, enables hydrogen atom transfer via reversible substrate binding. A wide range of aryl, heteroaryl, olefinic, and alkyl amides, including pharmaceutical derivatives, were converted to nitriles with high functional group tolerance and scalability. Spectroscopic and computational analyses support a mechanism involving oxidative quenching and selective hydrogen atom abstraction. This work establishes QQ photosensitizers as a practical toolkit for mild and versatile amide-to-nitrile conversion. Physical sciences/Chemistry/Photochemistry/Photocatalysis Physical sciences/Chemistry/Catalysis/Photocatalysis Physical sciences/Chemistry/Catalysis/Catalyst synthesis Physical sciences/Chemistry/Organic chemistry Physical sciences/Chemistry/Catalysis/Catalytic mechanisms Full Text Additional Declarations There is NO Competing Interest. Supplementary Files CartesianCoordinates.zip Cartesian coordinates of optimized structures QQPyHHOAc.cif Crystallographic data of QQ-PyH-HOAc QQMes.cif Crystallographic data of QQ-Mes SupportingInformation.pdf Supporting information Cite Share Download PDF Status: Posted Version 1 posted 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-7770848","acceptedTermsAndConditions":true,"allowDirectSubmit":true,"archivedVersions":[],"articleType":"Article","associatedPublications":[],"authors":[{"id":524094959,"identity":"0f7ac8b8-c49f-4907-b44c-25752bc5c54e","order_by":0,"name":"Jinwoo 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