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Synthesis of Tetracoordinate Boron‐Fused Benzoaceanthrylene Analogs via Tandem Electrophilic C−H Borylation
Author(s) -
Oda Susumu,
Abe Hiroaki,
Yasuda Nobuhiro,
Hatakeyama Takuji
Publication year - 2019
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201801682
Subject(s) - tetracoordinate , chemistry , annulation , borylation , ring (chemistry) , photochemistry , boron , electrophile , pyridine , heteroatom , crystallography , stereochemistry , medicinal chemistry , organic chemistry , aryl , alkyl , computer graphics (images) , computer science , planar , catalysis
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.