Premium
Boron‐Containing Polycyclic Aromatic Hydrocarbons: Facile Synthesis of Stable, Redox‐Active Luminophores
Author(s) -
Hertz Valentin M.,
Bolte Michael,
Lerner HansWolfram,
Wagner Matthias
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201502977
Subject(s) - luminophore , polycyclic aromatic hydrocarbon , boron , chemistry , carbon fibers , redox , aromaticity , photochemistry , combinatorial chemistry , organic chemistry , materials science , luminescence , molecule , optoelectronics , composite number , composite material
Abstract Herein we show that replacing the two meso carbon atoms of the polycyclic aromatic hydrocarbon (PAH) bisanthene by boron atoms transforms a near‐infrared dye into an efficient blue luminophore. This observation impressively illustrates the impact of boron doping on the frontier orbitals of PAHs. To take full advantage of this tool for the targeted design of organic electronic materials, the underlying structure–property relationships need to be further elucidated. We therefore developed a modular synthesis sequence based on a Peterson olefination, a stilbene‐type photocyclization, and an Si–B exchange reaction to substantially broaden the palette of accessible polycyclic aromatic organoboranes and to permit a direct comparison with their PAH congeners.