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1,2,5,6‐Tetrakis(guanidino)‐Naphthalenes: Electron Donors, Fluorescent Probes and Redox‐Active Ligands
Author(s) -
Lohmeyer Lukas,
Kaifer Elisabeth,
Wadepohl Hubert,
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.201905471
Subject(s) - redox , protonation , chemistry , photochemistry , fluorescence , naphthalene , quantum yield , yield (engineering) , inorganic chemistry , organic chemistry , ion , physics , materials science , quantum mechanics , metallurgy
New redox‐active 1,2,5,6‐tetrakis(guanidino)‐naphthalene compounds, isolable and storable in the neutral and deep‐green dicationic redox states and oxidisable further in two one‐electron steps to the tetracations, are reported. Protonation switches on blue fluorescence, with the fluorescence intensity (quantum yield) increasing with the degree of protonation. Reactions with N ‐halogenosuccinimides or N ‐halogenophthalimides led to a series of new redox‐active halogeno‐ and succinimido‐/phthalimido‐substituted derivatives. These highly selective reactions are proposed to proceed via the tri‐ or tetracationic state as the intermediate. The derivatives are oxidised reversibly at slightly higher potentials than that of the unsubstituted compounds to dications and further to tri‐ and tetracations. The integration of redox‐active ligands in the transition‐metal complexes shifts the redox potentials to higher values and also allows reversible oxidation in two potentially separated one‐electron steps.