para –Phenylenediamine Dimer as a Redox–Active Guest for Supramolecular Systems

Abstract: 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 α‐CD and β‐CD, a 1: 2 complex with γ‐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.

Object Details

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

References and Relationships

• Bibliographic citation: para –Phenylenediamine Dimer as a Redox–Active Guest for Supramolecular Systems ; day:21 ; month:03 ; year:2024 ; extent:13 ; Chemistry - a European journal ; (21.03.2024) (gesamt 13)

Contributors, Places and Time

• Creator: Janovský, Petr ; Springer, Andreas ; Filip, Jaroslav ; Prucková, Zdeňka ; Nečas, Marek ; Rouchal, Michal ; Schalley, Christoph A. ; Vícha, Robert

Further information

• DOI: 10.1002/chem.202400535
• URN: urn:nbn:de:101:1-2024032213032735442414
• Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
• Last update: 14.08.2025, 11:00 AM CEST