Publication Date:
2014-06-10
Description:
A new derivative of the previously reported 1,2-bis(benzimidazol-2-yl)ethane motif, cation [1H 2 ] 2+ , was synthesized under microwave irradiation and fully characterized by solution NMR, high-resolution mass spectrometry , cyclic voltammetry and X-ray crystallography. This cation presents a linear geometry and incorporates nitro substituents as electrochemical handles. In solution, cation [1H 2 ] 2+ , is capable of threading the cavity of dibenzo-24-crown-8 ether host (DB24C8) giving rise to a [2]pseudorotaxane complex [1H 2 ⊂DB24C8] 2+ , regardless of the counterion, [CF 3 SO 3 ] − or [CF 3 COO] − . The interpenetrated structure of [1H 2 ⊂DB24C8] 2+ was proven by solution NMR and X-ray crystallography. This host–guest complex is held together by several non-covalent interactions, such as hydrogen bonding and ion-dipole. An electrochemical study of [1H 2 ] 2+ in the presence of variable amounts of DB24C8 was performed; due to the irreversible redox behavior of cation [1H 2 ] 2+ , it was not possible to electrochemically control the association/dissociation process with DB24C8. Copyright © 2014 John Wiley & Sons, Ltd. A nitrobenzimidazol-based guest form a stable interpenetrated complex with dibenzo-24-crown-8 ether host in a [2]pseudorotaxane geometry that can be reversibly switched between complex and uncomplexed states in solution by means of the alternate addition of acid and base. The incorporation of electrochemically active nitro groups on the guest could provide a handle for electrochemical control of the association/dissociation process.
Print ISSN:
0894-3230
Electronic ISSN:
1099-1395
Topics:
Chemistry and Pharmacology
,
Physics
Permalink