%0 Journal Article %1 noauthororeditor %A Farrell, Jeffrey %A Mützel, Carina %A Bialas, David %A Rudolf, Maximilian %A Menekse, Kaan %A Krause, Ana-Maria %A Stolte, Matthias %A Würthner, Frank %D 2019 %J J. Am. Chem. Soc %K myown %N 22 %P 9096-9104 %R 10.1021/jacs.9b04675 %T Tunable Low-LUMO Boron-Doped Polycyclic Aromatic Hydrocarbons by General One-Pot C–H Borylations %U https://pubs.acs.org/doi/abs/10.1021/jacs.9b04675 %V 141 %X Boron-doping has long been recognized as a promising LUMO energy-lowering modification of graphene and related polycyclic aromatic hydrocarbons (PAHs). Unfortunately, synthetic difficulties have been a significant bottleneck for the understanding, optimization, and application of precisely boron-doped PAHs for optoelectronic purposes. Herein, a facile one-pot hydroboration electrophilic borylation cascade/dehydrogenation approach from simple alkene precursors is coupled with postsynthetic B-substitution to give access to ten ambient-stable core- and periphery-tuned boron-doped PAHs. These include large hitherto unknown doubly boron-doped analogues of anthanthrene and triangulene. Crystallographic, optical, electrochemical, and computational studies were performed to clarify the effect of boron-doped PAH shape, size, and structure on optoelectronic properties. Our molecular tuning allowed the synthesis of molecules exhibiting visible-range absorption, near-unity fluorescence quantum yields, and, to our knowledge, the most facile electrochemical reductions of any reported ambient-stable boron-doped PAHs (corresponding to LUMO energy levels as low as fullerenes). Finally, our study describes the first implementation of a precise three-coordinate boron-substituted PAH as an acceptor material in organic solar cells with power conversion efficiencies (PCEs) of up to 3%.

@article{noauthororeditor, abstract = {Boron-doping has long been recognized as a promising LUMO energy-lowering modification of graphene and related polycyclic aromatic hydrocarbons (PAHs). Unfortunately, synthetic difficulties have been a significant bottleneck for the understanding, optimization, and application of precisely boron-doped PAHs for optoelectronic purposes. Herein, a facile one-pot hydroboration electrophilic borylation cascade/dehydrogenation approach from simple alkene precursors is coupled with postsynthetic B-substitution to give access to ten ambient-stable core- and periphery-tuned boron-doped PAHs. These include large hitherto unknown doubly boron-doped analogues of anthanthrene and triangulene. Crystallographic, optical, electrochemical, and computational studies were performed to clarify the effect of boron-doped PAH shape, size, and structure on optoelectronic properties. Our molecular tuning allowed the synthesis of molecules exhibiting visible-range absorption, near-unity fluorescence quantum yields, and, to our knowledge, the most facile electrochemical reductions of any reported ambient-stable boron-doped PAHs (corresponding to LUMO energy levels as low as fullerenes). Finally, our study describes the first implementation of a precise three-coordinate boron-substituted PAH as an acceptor material in organic solar cells with power conversion efficiencies (PCEs) of up to 3%.}, added-at = {2019-10-14T10:53:58.000+0200}, author = {Farrell, Jeffrey and Mützel, Carina and Bialas, David and Rudolf, Maximilian and Menekse, Kaan and Krause, Ana-Maria and Stolte, Matthias and Würthner, Frank}, biburl = {https://www.bibsonomy.org/bibtex/2ac3266732f6d87014d701e558803f145/wuerthner_group}, doi = {10.1021/jacs.9b04675}, interhash = {0cd5ed9f1e45edcbc01ea32ad4febdb0}, intrahash = {ac3266732f6d87014d701e558803f145}, journal = {J. Am. Chem. Soc}, keywords = {myown}, month = may, number = 22, pages = {9096-9104}, timestamp = {2019-10-14T10:53:58.000+0200}, title = {Tunable Low-LUMO Boron-Doped Polycyclic Aromatic Hydrocarbons by General One-Pot C–H Borylations}, url = {https://pubs.acs.org/doi/abs/10.1021/jacs.9b04675}, volume = 141, year = 2019 }