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1,2,4,5‐Tetrakis(tetramethylguanidino)‐3,6‐diethynyl‐benzenes: Fluorescent Probes, Redox‐Active Ligands and Strong Organic Electron Donors
Author(s) -
Wagner Conrad,
Kreis Franka,
Popp Dennis,
Hübner Olaf,
Kaifer Elisabeth,
Himmel HansJörg
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.202001557
Subject(s) - chemistry , redox , cationic polymerization , reactivity (psychology) , fluorescence , photochemistry , guanidine , medicinal chemistry , catalysis , copper , benzene , polymer chemistry , inorganic chemistry , organic chemistry , physics , quantum mechanics , medicine , alternative medicine , pathology
In this work, the change of reactivity induced by the introduction of two para ‐ethynyl substituents (CCSi( i Pr) 3 or CCH) to the organic electron‐donor 1,2,4,5‐tetrakis(tetramethylguanidino)‐benzene is evaluated. The redox‐properties and redox‐state dependent fluorescence are evaluated, and dinuclear Cu I and Cu II complexes synthesized. The Lewis‐acidic B(C 6 F 5 ) 3 substitutes the proton of the ethynyl −CCH groups to give new anionic −CCB(C 6 F 5 ) 3 − substituents, leading eventually to a novel dianionic strong electron donor in its diprotonated form. Its two‐electron oxidation with dioxygen in the presence of a copper catalyst yields the first redox‐active guanidine that is neutral (instead of cationic) in its oxidized form.