1,2,5,6‐Tetrakis (guanidino)‐Naphthalenes: Electron Donors, Fluorescent Probes and Redox‐Active Ligands

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.

Location
Deutsche Nationalbibliothek Frankfurt am Main
Extent
Online-Ressource
Language
Englisch

Bibliographic citation
1,2,5,6‐Tetrakis (guanidino)‐Naphthalenes: Electron Donors, Fluorescent Probes and Redox‐Active Ligands ; volume:26 ; number:26 ; year:2020 ; pages:5834-5845 ; extent:12
Chemistry - a European journal ; 26, Heft 26 (2020), 5834-5845 (gesamt 12)

Creator
Lohmeyer, Lukas
Kaifer, Elisabeth
Wadepohl, Hubert
Himmel, Hans-Jörg

DOI
10.1002/chem.201905471
URN
urn:nbn:de:101:1-2022060417461821319530
Rights
Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
Last update
15.08.2025, 7:20 AM CEST

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