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Self‐assembly of a [2]pseudorotaxane complex by the threading of a nitrobenzimidazol‐based guest on dibenzo‐24‐crown ether host
Author(s) -
Castillo Dolores,
Cervantes Ruy,
Frontana Carlos,
Gonzalez Felipe J.,
Tiburcio Jorge
Publication year - 2014
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.3321
Subject(s) - chemistry , crown ether , supramolecular chemistry , hydrogen bond , crystallography , proton nmr , electrochemistry , cyclic voltammetry , stereochemistry , molecule , ion , crystal structure , organic chemistry , electrode
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.