Publication details
para–Phenylenediamine Dimer as a Redox–Active Guest for Supramolecular Systems
| Authors | |
|---|---|
| Year of publication | 2024 |
| Type | Article in Periodical |
| Magazine / Source | Chemistry - A European Journal |
| MU Faculty or unit | |
| Citation | |
| web | https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/chem.202400535 |
| Doi | http://dx.doi.org/10.1002/chem.202400535 |
| Keywords | cucurbiturils; cyclodextrins; host-guest systems; redox-active dye |
| Description | Redox–active components are highly valuable in the construction of molecular devices. We combined two p-phenylenediamines (p-PDA) with a biphenyl (BiPhe) unit to prepare a supramolecular guest 4 consisting of three binding sites for cucurbit[7/8]uril (CBn) and/or cyclodextrins (CD). Supramolecular properties of 4 were investigated using NMR, UV-vis, mass spectrometry and isothermal titration calorimetry. Our analysis revealed that 4 forms higher–order host–guest complexes, wherein a CD unit occupies the central BiPhe site, secured by two CBn units at the terminal p-PDA sites. Additionally, 1?:?1 complexes with ?-CD and ß-CD, a 1?:?2 complex with ?-CD and 2?:?1 complexes with CB7 and CB8 were identified. Through UV-vis and cyclic voltammetry, redox processes leading to the formation of a stable, deep blue dication diradical of 4 are elucidated. Furthermore, it is demonstrated that CB7 selectively protects oxidised 4 from reduction in the presence of a reducing agent. The supramolecular and redox properties of the structural motif represented by 4 render it an interesting candidate for the construction of supramolecular devices. |
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