%0 Journal Article %1 Tang2023 %A Tang, Ningning %A Zhou, Jiadong %A Wang, Liangxuan %A Stolte, Matthias %A Xie, Guojing %A Wen, Xinbo %A Liu, Linlin %A Würthner, Frank %A Gierschner, Johannes %A Xie, Zengqi %D 2023 %J Nat. Commun. %K myown %N 1 %P 1922 %R 10.1038/s41467-023-37171-y %T Anomalous deep-red luminescence of perylene black analogues with strong π-π interactions %U https://doi.org/10.1038/s41467-023-37171-y %V 14 %X 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 π-π ≈ 3.5 A, and longitudinal and transversal displacements of 3.1 A and 1.3 A; 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 ($þeta$) 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.

@article{Tang2023, 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 π-π ≈ 3.5 A, and longitudinal and transversal displacements of 3.1 A and 1.3 A; 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 ($\theta$) 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.}, added-at = {2024-07-22T14:06:15.000+0200}, author = {Tang, Ningning and Zhou, Jiadong and Wang, Liangxuan and Stolte, Matthias and Xie, Guojing and Wen, Xinbo and Liu, Linlin and Würthner, Frank and Gierschner, Johannes and Xie, Zengqi}, biburl = {https://www.bibsonomy.org/bibtex/2136b1fc680fd1331f6168de4e0b109c4/wuerthner_group}, day = 06, doi = {10.1038/s41467-023-37171-y}, interhash = {2146140aa74c3e538831b1b132f73336}, intrahash = {136b1fc680fd1331f6168de4e0b109c4}, issn = {2041-1723}, journal = {Nat. Commun.}, keywords = {myown}, month = apr, number = 1, pages = 1922, timestamp = {2024-11-26T10:01:13.000+0100}, title = {Anomalous deep-red luminescence of perylene black analogues with strong π-π interactions}, url = {https://doi.org/10.1038/s41467-023-37171-y}, volume = 14, year = 2023 }