How To Make Nitroaromatic Compounds Glow: Next-Generation Large X-Shaped, Centrosymmetric Diketopyrrolopyrroles

Skonieczny K, Papadopoulos I, Thiel D, Gutkowski K, Haines P, McCosker PM, Laurent AD, Keller PA, Clark T, Jacquemin D, Guldi DM, Gryko DT (2020)

Publication Type: Journal article

Publication year: 2020

Journal

Angewandte Chemie International Edition Wiley

DOI: 10.1002/anie.202005244

Abstract

Red-emissive pi-expanded diketopyrrolopyrroles (DPPs) with fluorescence reaching lambda=750 nm can be easily synthesized by a three-step strategy involving the preparation of diketopyrrolopyrrole followed by N-arylation and subsequent intramolecular palladium-catalyzed direct arylation. Comprehensive spectroscopic assays combined with first-principles calculations corroborated that both N-arylated and fused DPPs reach a locally excited (S-1) state after excitation, followed by internal conversion to states with solvent and structural relaxation, before eventually undergoing intersystem crossing. Only the structurally relaxed state is fluorescent, with lifetimes in the range of several nanoseconds and tens of picoseconds in nonpolar and polar solvents, respectively. The lifetimes correlate with the fluorescence quantum yields, which range from 6 % to 88 % in nonpolar solvents and from 0.4 % and 3.2 % in polar solvents. A very inefficient (T-1) population is responsible for fluorescence quantum yields as high as 88 % for the fully fused DPP in polar solvents.

Authors with CRIS profile

Ilias Papadopoulos Lehrstuhl für Physikalische Chemie I Dominik Thiel Lehrstuhl für Physikalische Chemie I Philipp Haines Lehrstuhl für Physikalische Chemie I Patrick Michael McCosker Lehrstuhl für Physikalische Chemie I Timothy Clark Naturwissenschaftliche Fakultät Dirk Michael Guldi Lehrstuhl für Physikalische Chemie I

Involved external institutions

Polska Akademia Nauk (PAN) / Polish Academy of Sciences PL Poland (PL) Université de Nantes FR France (FR) University of Wollongong (UOW) AU Australia (AU)

How to cite

APA:

Skonieczny, K., Papadopoulos, I., Thiel, D., Gutkowski, K., Haines, P., McCosker, P.M.,... Gryko, D.T. (2020). How To Make Nitroaromatic Compounds Glow: Next-Generation Large X-Shaped, Centrosymmetric Diketopyrrolopyrroles. Angewandte Chemie International Edition. https://doi.org/10.1002/anie.202005244

MLA:

Skonieczny, Kamil, et al. "How To Make Nitroaromatic Compounds Glow: Next-Generation Large X-Shaped, Centrosymmetric Diketopyrrolopyrroles." Angewandte Chemie International Edition (2020).

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