Issue 3, 2024

Using pyrrolizine-fused bipolar PAHs as a new strategy towards efficient red and NIR emissive dyes

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).

Graphical abstract: Using pyrrolizine-fused bipolar PAHs as a new strategy towards efficient red and NIR emissive dyes

Supplementary files

Article information

Article type
Research Article
Submitted
17 Nov 2023
Accepted
02 Dec 2023
First published
04 Dec 2023
This article is Open Access
Creative Commons BY license

Org. Chem. Front., 2024,11, 755-760

Using pyrrolizine-fused bipolar PAHs as a new strategy towards efficient red and NIR emissive dyes

K. Bartkowski, A. K. Gupta, T. Matulaitis, M. Morawiak, E. Zysman-Colman and M. Lindner, Org. Chem. Front., 2024, 11, 755 DOI: 10.1039/D3QO01914D

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