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Using pyrrolizine-fused bipolar PAHs as a new strategy towards efficient red and NIR emissive dyes
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dc.contributor.author | Bartkowski, Krzysztof | |
dc.contributor.author | Gupta, Abhishek Kumar | |
dc.contributor.author | Matulaitis, Tomas | |
dc.contributor.author | Morawiak, Maja | |
dc.contributor.author | Zysman-Colman, Eli | |
dc.contributor.author | Lindner, Marcin | |
dc.date.accessioned | 2023-12-21T09:30:02Z | |
dc.date.available | 2023-12-21T09:30:02Z | |
dc.date.issued | 2024-02-07 | |
dc.identifier | 297556837 | |
dc.identifier | f3723c82-ede6-4cd5-9f64-f0c31a2d7941 | |
dc.identifier | 85179806361 | |
dc.identifier.citation | Bartkowski , K , Gupta , A K , Matulaitis , T , Morawiak , M , Zysman-Colman , E & Lindner , M 2024 , ' Using pyrrolizine-fused bipolar PAHs as a new strategy towards efficient red and NIR emissive dyes ' , Organic Chemistry Frontiers , vol. 11 , no. 3 , pp. 755-760 . https://doi.org/10.1039/d3qo01914d | en |
dc.identifier.issn | 2052-4129 | |
dc.identifier.other | Jisc: 1605044 | |
dc.identifier.other | ORCID: /0000-0003-0470-7356/work/149332652 | |
dc.identifier.other | ORCID: /0000-0001-7183-6022/work/149333203 | |
dc.identifier.uri | https://hdl.handle.net/10023/28916 | |
dc.description | K. B. and M. L. acknowledge support from the National Centre for Research and Development, Poland, Grant No. LIDER/21/0077/L-11/19/NCBR/2020. M. L. is a recipient of a scholarship awarded by the Polish Ministry of Education and Science to outstanding young scientists (2/DSP/2021). The St Andrews team thanks the Leverhulme Trust (RPG-2022-032) and the Engineering and Physical Sciences Research Council (EP/R035164/1, EP/W007517) for support. | en |
dc.description.abstract | We report the synthesis and characterization of the first pyrrolizine-embedded PAH systems. The bipolar core, based on a naphthalimide and indole fusion, was successfully synthesized through a one-pot cascade of Suzuki/Boc deprotection/Buchwald–Hartwig transformations. A facile post-functionalization of the unoccupied β-position of the heterocycle with aromatic amines as donor subunits led to a set of donor–acceptor architecture-based dyes. Effective narrowing of the HOMO–LUMO gap, along with its tuning by changing donor strength together with stabilization of π conjugation within the pyrrolizine–NMI core, provided a route to near-infrared (NIR) emission not only in solution (∼740 nm) but also in the solid-state (∼700 nm). | |
dc.format.extent | 6 | |
dc.format.extent | 1753885 | |
dc.language.iso | eng | |
dc.relation.ispartof | Organic Chemistry Frontiers | en |
dc.subject | QD Chemistry | en |
dc.subject | DAS | en |
dc.subject.lcc | QD | en |
dc.title | Using pyrrolizine-fused bipolar PAHs as a new strategy towards efficient red and NIR emissive dyes | en |
dc.type | Journal article | en |
dc.contributor.sponsor | The Leverhulme Trust | en |
dc.contributor.sponsor | EPSRC | en |
dc.contributor.sponsor | UK Research and Innovation | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.contributor.institution | University of St Andrews. Institute of Behavioural and Neural Sciences | en |
dc.contributor.institution | University of St Andrews. EaSTCHEM | en |
dc.contributor.institution | University of St Andrews. Centre for Energy Ethics | en |
dc.contributor.institution | University of St Andrews. Organic Semiconductor Centre | en |
dc.identifier.doi | 10.1039/d3qo01914d | |
dc.description.status | Peer reviewed | en |
dc.identifier.grantnumber | RPG-2022-032 | en |
dc.identifier.grantnumber | EP/R035164/1 | en |
dc.identifier.grantnumber | EP/W007517/1 | en |
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