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.
%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
}