Dipyrrolonaphthyridinedione – (still) a mysterious cross-conjugated chromophore

Sadowski, Bartłomiej; Gryko, Daniel T.

Dipyrrolonaphthyridinedione – (still) a mysterious cross-conjugated chromophore

dc.contributor.author	Sadowski, Bartłomiej
dc.contributor.author	Gryko, Daniel T.
dc.contributor.organization	Institute of Organic Chemistry, Polish Academy of Sciences	en
dc.contributor.organization	Centre of New Technologies, University of Warsaw	en
dc.date.accessioned	2024-01-08T14:06:15Z
dc.date.available	2024-01-08T14:06:15Z
dc.date.issued	2023
dc.description.abstract	Dipyrrolonaphthyridinediones (DPNDs) entered the chemical world in 2016. This cross-conjugated donor–acceptor skeleton can be prepared in two steps from commercially available reagents in overall yieldz15–20% (5 mmol scale). DPNDs can be easily and regioselectively halogenated which opens an avenue to numerous derivatives as well as to p-expansion. Although certain synthetic limitations exist, the current derivatization possibilities provided impetus for numerous explorations that use DPNDs. Structural modifications enable bathochromic shift of the emission to deep-red region and reaching the optical brightness 30 000 M−1 cm−1. Intense absorption and strong emission of greenish-yellow light attracted the interest which eventually led to the discovery of their strong two-photon absorption, singlet fission in the crystalline phase and triplet sensitization. Dipyrrolonaphthyridinedione-based twistacenes broadened our knowledge on the influence of twisting angle on the fate of the molecule in the excited state. Collectively, these findings highlight the compatibility of DPNDs with various applications within organic optoelectronics.	en
dc.description.sponsorship	Polish National Science Centre (Sonata 2021/43/D/ST4/02267 and OPUS 2020/37/B/ST4/00017) ; EU's Horizon 2020 research and innovation programme under Grant Agreement No. 860762
dc.identifier.citation	Chem. Sci., 2023, 14, 14020 ; http://pubs.rsc.org/en/content/articlepdf/2023/SC/D3SC05272A	en
dc.identifier.doi	10.1039/d3sc05272a
dc.identifier.issn	2041-6520
dc.identifier.issn	2041-6539
dc.identifier.uri	https://open.icm.edu.pl/handle/123456789/23522
dc.language.iso	en
dc.publisher	Royal Society of Chemistry	en
dc.rights	Uznanie autorstwa-Użycie niekomercyjne 3.0 Unported	*
dc.rights.uri	http://creativecommons.org/licenses/by-nc/3.0/	*
dc.title	Dipyrrolonaphthyridinedione – (still) a mysterious cross-conjugated chromophore	en
dc.type	article	en