%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 $\pi$-$\pi$ 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 $\pi$−$\pi$ 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 $\pi$ stacking arrangement (exhibiting d$\pi$−$\pi$ ≈ 3.5þinspace\AA, and longitudinal and transversal displacements of 3.1þinspace\AA and 1.3þinspace\AA); however, they afford deep-red emitters with solid-state fluorescence quantum yields ($\Phi$F) 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 $\Phi$F 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 $\pi$−$\pi$ 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 $\pi$ stacking arrangement (exhibiting d$\pi$−$\pi$ ≈ 3.5{\thinspace}{\AA}, and longitudinal and transversal displacements of 3.1{\thinspace}{\AA} and 1.3{\thinspace}{\AA}); however, they afford deep-red emitters with solid-state fluorescence quantum yields ($\Phi$F) 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 $\Phi$F 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 W{\"u}rthner, Frank and Gierschner, Johannes and Xie, Zengqi}, biburl = {https://www.bibsonomy.org/bibtex/27b75958c7c46e558978c034913d56487/wuerthner_group}, day = 06, doi = {10.1038/s41467-023-37171-y}, interhash = {b3885936045db1978c30d65103a66079}, intrahash = {7b75958c7c46e558978c034913d56487}, issn = {2041-1723}, journal = {Nat. Commun.}, keywords = {myown}, month = apr, number = 1, pages = 1922, timestamp = {2024-07-22T14:06:15.000+0200}, title = {Anomalous deep-red luminescence of perylene black analogues with strong $\pi$-$\pi$ interactions}, url = {https://doi.org/10.1038/s41467-023-37171-y}, volume = 14, year = 2023 }