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Multi‐Stage Redox Systems Based on Dicationic P‐Containing Polycyclic Aromatic Hydrocarbons
Author(s) -
Delouche Thomas,
Vacher Antoine,
Caytan Elsa,
Roisnel Thierry,
Le Guennic Boris,
Jacquemin Denis,
Hissler Muriel,
Bouit PierreAntoine
Publication year - 2020
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.202001213
Subject(s) - delocalized electron , redox , chemistry , cyclic voltammetry , electrochemistry , photochemistry , electron paramagnetic resonance , electron delocalization , polycyclic aromatic hydrocarbon , radical ion , inorganic chemistry , organic chemistry , electrode , ion , physics , nuclear magnetic resonance
We report the straightforward synthesis of unprecedented electron‐acceptors based on dicationic P‐containing PAHs (Polycyclic Aromatic Hydrocarbons) based on copper mediated radical approach. In these systems, two phosphoniums are connected through various PAHs backbones. The impact of π‐extension on both the optical and redox properties is investigated using a joint experimental (UV/Vis absorption, fluorescence and cyclic voltammetry) and theoretical approach (TD‐DFT calculations). Finally, (spectro)‐electrochemical studies prove that these compounds possess three redox states and EPR studies confirm the in situ formation of an organic radical delocalized on the PAH backbone.