1,2,5,6-tetrakis(guanidino)-naphthalenes

• Verfasst von: Lohmeyer, Lukas [VerfasserIn]
• Verfasst von: Kaifer, Elisabeth [VerfasserIn]
• Verfasst von: Wadepohl, Hubert [VerfasserIn]
• Verfasst von: Himmel, Hans-Jörg [VerfasserIn]
• Titel: 1,2,5,6-tetrakis(guanidino)-naphthalenes
• Titelzusatz: electron donors, fluorescent probes and redox-active ligands
• Verf.angabe: Lukas Lohmeyer, Elisabeth Kaifer, Hubert Wadepohl, and Hans-Jörg Himmel
• Jahr: 2020
• Umfang: 12 S.
• Fussnoten: Version of record online: April 21, 2020 ; Gesehen am 25.11.2021
• Titel Quelle: Enthalten in: Chemistry - a European journal
• Ort Quelle: Weinheim : Wiley-VCH, 1995
• Jahr Quelle: 2020
• Band/Heft Quelle: 26(2020), 26, Seite 5834-5845
• ISSN Quelle: 1521-3765
• DOI: doi:10.1002/chem.201905471
• Datenträger: Online-Ressource
• Sprache: eng
• Sach-SW: aromatic substitution
• Sach-SW: electron donors
• Sach-SW: guanidines
• Sach-SW: oxidation
• Sach-SW: protonation
• K10plus-PPN: 1779068786
• K10plus-PPN:
  Universitätsbibliothek
• Lokale URL UB: Zum Volltext

Abstract

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.