Using pyrrolizine-fused bipolar PAHs as a new strategy towards efficient red and NIR emissive dyes
Date
07/02/2024Author
Grant ID
RPG-2022-032
EP/R035164/1
EP/W007517/1
Metadata
Show full item recordAbstract
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).
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
Publication
Organic Chemistry Frontiers
Status
Peer reviewed
ISSN
2052-4129Type
Journal article
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.Collections
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