Synthesis of Tetracoordinate Boron‐Fused Benzoaceanthrylene Analogs via Tandem Electrophilic C−H Borylation

Benzoaceanthrylene analogs with tetracoordinate boron at the ring junction were synthesized through tandem electrophilic C−H borylation of 2,6‐dinaphthylpyridine followed by nucleophilic substitution. Notably, the [5,6]‐annulation occurred selectively over [6,6]‐annulation with the assistance of nit...

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Bibliographic Details
Published in:Chemistry, an Asian journal an Asian journal, 2019-05, Vol.14 (10), p.1657-1661
Main Authors: Oda, Susumu, Abe, Hiroaki, Yasuda, Nobuhiro, Hatakeyama, Takuji
Format: Article
Language:English
Subjects:
Analogs
benzoaceanthrylene
Boron
Chemical reactions
Chemistry
Crystallography
Electrochemical analysis
Electron affinity
electrophilic C−H borylation
five-membered rings
Fluorine
Ionization potentials
Organic chemistry
pi-conjugated compounds
tetracoordinate boron
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Summary:Benzoaceanthrylene analogs with tetracoordinate boron at the ring junction were synthesized through tandem electrophilic C−H borylation of 2,6‐dinaphthylpyridine followed by nucleophilic substitution. Notably, the [5,6]‐annulation occurred selectively over [6,6]‐annulation with the assistance of nitrogen coordination of the pyridine ring. The X‐ray crystallographic analysis revealed the polycyclic skeleton with a distorted tetracoordinate boron atom and a unique packing structure with intermolecular π–π interaction. The photophysical and electrochemical properties of these benzoaceanthrylene analogs were evaluated by UV‐vis spectroscopy and differential pulse voltammetry. The electron affinity of the fluorine‐substituted derivative is estimated to be 3.49 eV from the ionization potential and optical band gap. Thus, this derivative is expected to be a promising n‐type semiconducting material. Get your kicks on route 66: Tetracoordinate boron‐fused benzoaceanthrylene analogs were synthesized through tandem electrophilic C−H borylation and successive nucleophilic substitution. In this reaction, nitrogen‐assisted [5,6]‐annulation proceeded preferentially over [6,6]‐annulation. The prepared compounds adopted a unique packing structure with intermolecular π–π interaction and have high electron affinity, expected to be promising n‐type semiconducting materials.
ISSN:1861-4728
1861-471X
DOI:10.1002/asia.201801682