Anomalous deep-red luminescence of perylene black analogues with strong π-π interactions

Ningning Tang, Jiadong Zhou (), Liangxuan Wang, Matthias Stolte, Guojing Xie, Xinbo Wen, Linlin Liu, Frank Würthner (), Johannes Gierschner () and Zengqi Xie ()
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Ningning Tang: South China University of Technology
Jiadong Zhou: South China University of Technology
Liangxuan Wang: IMDEA Nanoscience, Ciudad Universitaria de Cantoblanco
Matthias Stolte: Julius-Maximilians-Universität Würzburg, Am Hubland
Guojing Xie: South China University of Technology
Xinbo Wen: South China University of Technology
Linlin Liu: South China University of Technology
Frank Würthner: Julius-Maximilians-Universität Würzburg, Am Hubland
Johannes Gierschner: IMDEA Nanoscience, Ciudad Universitaria de Cantoblanco
Zengqi Xie: South China University of Technology

Nature Communications, 2023, vol. 14, issue 1, 1-10

Abstract: Abstract Perylene bisimide (PBI) dyes are known as red, maroon and black pigments, whose colors depend on the close π−π stacking arrangement. However, contrary to the luminescent monomers, deep-red and black PBI pigments are commonly non- or only weakly fluorescent due to (multiple) quenching pathways. Here, we introduce N-alkoxybenzyl substituted PBIs that contain close π stacking arrangement (exhibiting dπ−π ≈ 3.5 Å, and longitudinal and transversal displacements of 3.1 Å and 1.3 Å); however, they afford deep-red emitters with solid-state fluorescence quantum yields (ΦF) of up to 60%. Systematic photophysical and computational studies in solution and in the solid state reveal a sensitive interconversion of the PBI-centred locally excited state and a charge transfer state, which depends on the dihedral angle (θ) between the benzyl and alkoxy groups. This effectively controls the emission process, and enables high ΦF by circumventing the common quenching pathways commonly observed for perylene black analogues.

Date: 2023
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DOI: 10.1038/s41467-023-37171-y

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