Reductive Transformation of Imine Covalent Organic Frameworks into Emissive Polymers: Insights into Emission Quenching

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dc.contributor.authorTyszka-Gumkowska, Agata
dc.contributor.authorBrzeziński, Mateusz
dc.contributor.authorGawinkowski, Sylwester
dc.contributor.authorPolczyk, Tomasz
dc.contributor.authorWegner, Wojciech
dc.contributor.authorWlazło, Mateusz
dc.contributor.authorBernatowicz, Piotr
dc.contributor.authorNawrocki, Jan
dc.contributor.authorGaweł, Przemysław
dc.contributor.authorNoworyta, Krzysztof
dc.contributor.authorOstapko, Jakub
dc.contributor.organizationCentre of Excellence ENSEMBLE3, Warsaw
dc.contributor.organizationInstitute of Physical Chemistry, Polish Academy of Sciences
dc.contributor.organizationFaculty of Chemistry, Jagiellonian University
dc.contributor.organizationCenter of New Technologies, University of Warsaw
dc.contributor.organizationInstitute of Organic Chemistry, Polish Academy of Sciences
dc.date.accessioned2025-10-24T13:51:02Z
dc.date.available2025-10-24T13:51:02Z
dc.date.issued2025
dc.date.submitted2025-10-24T12:17:35Zen
dc.description.abstractAlthough imine-linked covalent organic frameworks (COFs) are readily synthesized, their lack of intrinsic emission constrains their potential in optoelectronic applications. Moreover, the underlying mechanisms governing excited-state energy dissipation remain poorly understood. To overcome these limitations, we present a straightforward strategy to transform nonemissive, anthracene-based imine-COFs (im-COF) into highly emissive amine-based covalent organic polymers (am-COP) through NaBH3CN/benzoic acid reduction, achieving solid-state emission quantum yields of up to 30%. To clarify the excited-state energy dissipation mechanisms in COFs and COPs, we synthesized molecular reference compounds featuring either imine or amine functionalities. Photophysical studies, supported by density functional theory (DFT) calculations, reveal that the excited states of both amines and imines exhibit weak charge transfer (CT) properties. Furthermore, a comparative analysis of the photophysical behavior of molecular references, im-COFs, and am-COPs demonstrates that the polymer emission arising from charge-transfer processes is modulated by the polymer’s intrinsic polarity. These findings provide fundamental insights into the photophysical behavior of COFs, thus paving the way for the development of emissive porous materials with promising advanced applications.en
dc.description.sponsorshipNational Science Center, Poland, Sonata Grant 2022/47/D/ST5/01375; Polish high-performance computing infrastructure PLGrid (HPC Center: ACK Cyfronet AGH), Computational Grant PLG/2024/017906; Wroclaw Centre for Networking and Supercomputing (http://wcss.pl); “ENSEMBLE3-Center of Excellence, project (GA MAB/2020/14), International Research Agenda programs of the Foundation for Polish Science that are cofinanced by the European Union under the European Regional Development Fund and the European Union Horizon 2020, program Teaming for Excellence (GA 857543).
dc.identifier.citationChem. Mater. 2025, 37, 19, 8048–8058 // https://doi.org/10.1021/acs.chemmater.5c01951
dc.identifier.doi10.1021/acs.chemmater.5c01951
dc.identifier.issn0897-4756
dc.identifier.issn1520-5002
dc.identifier.urihttps://open.icm.edu.pl/handle/123456789/26246
dc.language.isoen
dc.publisherAmerican Chemical Society
dc.relation.ispartofseries37; 19
dc.rightsUznanie autorstwa 4.0 Międzynarodoween
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/
dc.sourceChemistry of Materials
dc.titleReductive Transformation of Imine Covalent Organic Frameworks into Emissive Polymers: Insights into Emission Quenchingen
dc.typearticle
dc.type.versionpublishedVersion
person.identifier.orcidGaweł, Przemysław [0000-0003-1555-376X]
person.identifier.orcidBrzeziński, Mateusz [0009-0001-9593-197X]
person.identifier.orcidGawinkowski, Sylwester [0000-0001-5315-6197]
person.identifier.orcidBernatowicz, Piotr [0000-0001-8891-0380]
person.identifier.orcidNawrocki, Jan [0000-0001-5124-4273]
person.identifier.orcidOstapko, Jakub [0000-0002-0129-2418]
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