%0 Journal Article %1 D4QO00421C %A Mützel, Carina %A Shoyama, Kazutaka %A Krause, Ana-Maria %A Würthner, Frank %D 2024 %I The Royal Society of Chemistry %J Org. Chem. Front. %K myown %N 10 %P 2747-2755 %R 10.1039/D4QO00421C %T Synthesis of a helical boron-doped PAH by post-functionalization of 3,9-diboraperylene %U http://dx.doi.org/10.1039/D4QO00421C %V 11 %X We present herein the post-functionalization of doubly boron-doped polycyclic aromatic hydrocarbons (PAHs) by various aryl substituents, namely the syntheses of a series of (2,8,)3,9-aryl-substituted 3,9-diboraperylenes via boron-substitution of (2,8-diaryl-)3,9-dihydroxy-3,9-diboraperylenes. These new boron-doped PAHs exhibit two reversible reductions with a remarkably facile first reduction between E = −1.04 and −1.13 V vs. Fc+/Fc. Friedel–Crafts cyclization of the 2-isopropenylnaphthyl-substituted derivative afforded a helical boron-doped polycyclic aromatic hydrocarbon that is endowed with a low LUMO level, high absorption coefficients and fluorescence (ΦF = 0.73), combined with a one-dimensional π–π stacking interaction in the solid state.

@article{D4QO00421C, abstract = {We present herein the post-functionalization of doubly boron-doped polycyclic aromatic hydrocarbons (PAHs) by various aryl substituents, namely the syntheses of a series of (2,8,)3,9-aryl-substituted 3,9-diboraperylenes via boron-substitution of (2,8-diaryl-)3,9-dihydroxy-3,9-diboraperylenes. These new boron-doped PAHs exhibit two reversible reductions with a remarkably facile first reduction between E = −1.04 and −1.13 V vs. Fc+/Fc. Friedel–Crafts cyclization of the 2-isopropenylnaphthyl-substituted derivative afforded a helical boron-doped polycyclic aromatic hydrocarbon that is endowed with a low LUMO level, high absorption coefficients and fluorescence (ΦF = 0.73), combined with a one-dimensional π–π stacking interaction in the solid state.}, added-at = {2024-05-15T09:32:56.000+0200}, author = {Mützel, Carina and Shoyama, Kazutaka and Krause, Ana-Maria and Würthner, Frank}, biburl = {https://www.bibsonomy.org/bibtex/2159e9a7cda6905f45f7c40fbe61cc7c9/wuerthner_group}, doi = {10.1039/D4QO00421C}, interhash = {91ee47d1b366dd922c2fdc1c9c2d47a2}, intrahash = {159e9a7cda6905f45f7c40fbe61cc7c9}, journal = {Org. Chem. Front.}, keywords = {myown}, number = 10, pages = {2747-2755}, publisher = {The Royal Society of Chemistry}, timestamp = {2024-05-15T09:32:56.000+0200}, title = {Synthesis of a helical boron-doped PAH by post-functionalization of 3{,}9-diboraperylene}, url = {http://dx.doi.org/10.1039/D4QO00421C}, volume = 11, year = 2024 }