Organosulfur and Organoselenium Functionalized Benzimidazo[1,2-a]quinolines: From Experimental and Theoretical Photophysics to All-Solution-Processed OLEDs.

Autor: da Silva RB; Instituto de Química, Departamento de Química Orgânica, Universidade Federal do Rio Grande do Sul (UFRGS), PO Box 15003, Porto Alegre, Rio Grande do Sul, 91501-970, Brazil., Coelho FL; Instituto de Química, Universidade Federal de Goiás, Av. Esperança s/n, Campus Samambaia, Goiânia, Goias, 74690-900, Brazil., de Castro Silva Junior H; Instituto de Química, Departamento de Química Orgânica, Universidade Federal do Rio Grande do Sul (UFRGS), PO Box 15003, Porto Alegre, Rio Grande do Sul, 91501-970, Brazil., Germino JC; Department of Physics and i3N - Institute for Nanostructures, Nanomodelling and Nanofabrication, University of Aveiro, Aveiro, 3810-193, Portugal., Atvars TDZ; Chemistry Institute, University of Campinas, Campinas, 13083-872, Brazil., Rodembusch FS; Instituto de Química, Departamento de Química Orgânica, Universidade Federal do Rio Grande do Sul (UFRGS), PO Box 15003, Porto Alegre, Rio Grande do Sul, 91501-970, Brazil. rodembusch@iq.ufrgs.br., Duarte LGTA; Chemistry Institute, University of Campinas, Campinas, 13083-872, Brazil. lg.alvesduarte@gmail.com., Schneider PH; Instituto de Química, Departamento de Química Orgânica, Universidade Federal do Rio Grande do Sul (UFRGS), PO Box 15003, Porto Alegre, Rio Grande do Sul, 91501-970, Brazil. paulos@iq.ufrgs.br.
Jazyk: angličtina
Zdroj: Journal of fluorescence [J Fluoresc] 2024 May; Vol. 34 (3), pp. 1427-1439. Date of Electronic Publication: 2023 Aug 05.
DOI: 10.1007/s10895-023-03358-1
Abstrakt: In this study, we present the synthesis of benzimidazo[1,2-a] quinoline-based heterocycles bearing organosulfur and organoselenium moieties through transition-metal-free cascade reactions involving a sequential intermolecular aromatic nucleophilic substitution (SN Ar ). Both sulfur and selenium derivatives presented absorption maxima located around 355 nm related to spin and symmetry allowing electronic 1 π-π* transitions, and fluorescence emission at the violet-blue region (~440 nm) with relatively large Stokes shift. The fluorescence quantum yields were slightly influenced by the chalcogen, with the sulfur derivatives presenting higher values than the selenium analogs. In this sense, the quantum yields for selenium derivatives can probably be affected by the intersystem crossing or even the photoinduced electron transfer process (PET). The compounds were successfully applied in all-solution-processed organic light-emitting diodes (OLEDs), where poly(9-vinylcarbazole) was employed as a dispersive matrix generating single-layer device cells. The obtained electroluminescence spectra are a sum of benzimidazo[1,2-a]quinolines and PVK singlet and/or triplet emissive states, according to their respective energy band gaps. The best diode rendered a luminance of 25.4 cd⋅m -2 with CIE (0.17, 0.14) and current efficiency of 20.2 mcd⋅A -1 , a fivefold improvement in comparison to the PVK device that was explained by a 50-fold increase of charge-carriers electrical mobility.
(© 2023. The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature.)
Databáze: MEDLINE
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