Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 138, Issue 36, Pages 11606-11615Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b04445
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Funding
- National Basic Research Program of China (973 Program) [2013CBA01602, 2012CB933404]
- National Natural Science Foundation of China [21574080]
- Shanghai Committee of Science and Technology [15JC1490500]
- German Research Foundation (DFG) [EXC 1056, OR 349/1]
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A novel class of dibenzo-fused 1,9-diaza-9a-boraphenalenes featuring zigzag edges with a nitrogen boron nitrogen bonding pattern named NBN-dibenzophenalenes (NBN-DBPs) has been synthesized: Alternating nitrogen and boron atoms impart high chemical stability to these zigzag-edged polycyclic aromatic hydrocarbons (PAHs), and this motif even allows for postsynthetic modifications, as demonstrated here through electrophilie bromination and subsequent palladium-catalyzed cross-coupling reactions. Upon oxidation, as a typical example, NBN-DBP 5a was nearly quantitatively converted to sigma-dimer 5a,-2 through an open-shell intermediate, as indicated by UV-vis-NIR absorption spectroscopy and electron paramagnetic resonance spectroscopy corroborated by spectroscopic calculations, as Well as 2D NMR spectra analyses. In situ spectroelectrochemistiy was used to confirm the formation process of the dimer radical cation 5a-2(center dot+). Finally, the developed new synthetic strategy could also be applied to obtain pi-extended NBN-clibentoheptazethrene (NBN-DBHZ), representing an efficient pathway toward NBN-doped zigzag-edged graphene nanoribbons.
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