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En Route to Stimuli‐Responsive Boron‐, Nitrogen‐, and Sulfur‐Doped Polycyclic Aromatic Hydrocarbons
Author(s) -
Hertz Valentin M.,
Massoth Julian G.,
Bolte Michael,
Lerner HansWolfram,
Wagner Matthias
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201602406
Subject(s) - solvatochromism , photochemistry , chemistry , sulfur , boron , cyclic voltammetry , polycyclic aromatic hydrocarbon , solvent , sulfoxide , photoluminescence , dibenzothiophene , redox , absorption spectroscopy , nitrogen , spectroscopy , organic chemistry , materials science , electrochemistry , physics , optoelectronics , electrode , quantum mechanics
Replacing both meso carbon atoms of the polycyclic aromatic hydrocarbon (PAH) bisanthene by boron atoms creates an efficient blue fluorophore with a strong electron‐accepting character. The corresponding meso ‐B,S‐doped bisanthene exhibits a solvent‐dependent green‐to‐orange photoluminescence and undergoes a reversible reduction at E1 / 2 =−2.06 V (vs. FcH/FcH + ). After oxidation of the sulfur atom, the resulting sulfoxide emits in the blue range of the spectrum, shows only negligible solvatochromism, and a reversible redox transition at E1 / 2 =−1.74 V. Several related B, N‐ and B, S‐containing PAHs have been prepared following the same modular synthetic procedure and are also described herein. In order to systematically compare their optoelectronic properties, all products have been investigated by cyclic voltammetry as well as UV/Vis absorption/emission spectroscopy.