ja9b04675_si_003.cif (423.06 kB)
Tunable Low-LUMO Boron-Doped Polycyclic Aromatic Hydrocarbons by General One-Pot C–H Borylations
dataset
posted on 2019-05-20, 18:37 authored by Jeffrey
M. Farrell, Carina Mützel, David Bialas, Maximilian Rudolf, Kaan Menekse, Ana-Maria Krause, Matthias Stolte, Frank WürthnerBoron-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%.
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boron-doped analoguesoptoelectronic purposesboron-doped PAHsLUMO energy-lowering modificationoptoelectronic propertiespower conversion efficienciesambient-stable boron-doped PAHsPCEthree-coordinate boron-substituted PAHpostsynthetic B-substitutionambient-stable coreelectrochemical reductionsTunable Low-LUMO Boron-Doped Polycyclic Aromatic Hydrocarbonsperiphery-tuned boron-doped PAHsboron-doped PAH shapeLUMO energy levelsnear-unity fluorescence quantum yieldsacceptor materialalkene precursorsvisible-range absorption
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