Issue 48, 2023

Dipyrrolonaphthyridinedione – (still) a mysterious cross-conjugated chromophore

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 yield ≈15–20% (5 mmol scale). DPNDs can be easily and regioselectively halogenated which opens an avenue to numerous derivatives as well as to π-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.

Graphical abstract: Dipyrrolonaphthyridinedione – (still) a mysterious cross-conjugated chromophore

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Article information

Article type
Perspective
Submitted
05 10 2023
Accepted
08 11 2023
First published
10 11 2023
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2023,14, 14020-14038

Dipyrrolonaphthyridinedione – (still) a mysterious cross-conjugated chromophore

B. Sadowski and D. T. Gryko, Chem. Sci., 2023, 14, 14020 DOI: 10.1039/D3SC05272A

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