1,2,4,5-Tetrakis(tetramethylguanidino)-3,6-diethynyl-benzenes: fluorescent probes, redox-active ligands and strong organic electron donors
In this work, the change of reactivity induced by the introduction of two para-ethynyl substituents (CCSi(iPr)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...
Saved in:
| Main Authors: | , , , , , |
|---|---|
| Format: | Article (Journal) |
| Language: | English |
| Published: |
2020
|
| In: |
Chemistry - a European journal
Year: 2020, Volume: 26, Issue: 45, Pages: 10336-10347 |
| ISSN: | 1521-3765 |
| DOI: | 10.1002/chem.202001557 |
| Online Access: | Verlag, kostenfrei, Volltext: https://doi.org/10.1002/chem.202001557 Verlag, kostenfrei, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.202001557 
|
| Author Notes: | Conrad Wagner, Franka Kreis, Dennis Popp, Olaf Hübner, Elisabeth Kaifer, and Hans-Jörg Himmel |
| Summary: | In this work, the change of reactivity induced by the introduction of two para-ethynyl substituents (CCSi(iPr)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 CuI and CuII complexes synthesized. The Lewis-acidic B(C6F5)3 substitutes the proton of the ethynyl −CCH groups to give new anionic −CCB(C6F5)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. |
|---|---|
| Item Description: | First published: 05 May 2020 Gesehen am 10.11.2021 |
| Physical Description: | Online Resource |
| ISSN: | 1521-3765 |
| DOI: | 10.1002/chem.202001557 |