1,2,5,6-tetrakis(guanidino)-naphthalenes: electron donors, fluorescent probes and redox-active ligands
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 intensi...
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| Main Authors: | , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
2020
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| In: |
Chemistry - a European journal
Year: 2020, Volume: 26, Issue: 26, Pages: 5834-5845 |
| ISSN: | 1521-3765 |
| DOI: | 10.1002/chem.201905471 |
| Online Access: | Verlag, kostenfrei, Volltext: https://doi.org/10.1002/chem.201905471 Verlag, kostenfrei, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201905471 
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| Author Notes: | Lukas Lohmeyer, Elisabeth Kaifer, Hubert Wadepohl, and Hans-Jörg Himmel |
| Summary: | 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. |
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| Item Description: | Version of record online: April 21, 2020 Gesehen am 25.11.2021 |
| Physical Description: | Online Resource |
| ISSN: | 1521-3765 |
| DOI: | 10.1002/chem.201905471 |