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A Halogen Bonding 1,3‐Disubstituted Ferrocene Receptor for Recognition and Redox Sensing of Azide
Author(s) -
Lim Jason Y. C.,
Beer Paul D.
Publication year - 2017
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201600805
Subject(s) - chemistry , ferrocene , azide , halogen bond , redox , hydrogen bond , electrochemistry , photochemistry , combinatorial chemistry , cyclopentadienyl complex , inorganic chemistry , organic chemistry , molecule , electrode , catalysis
A neutral redox‐active acyclic halogen bonding (XB) receptor with a ferrocene core functionalised at the 1,3‐positions of a cyclopentadienyl ring with iodotriazole motifs is prepared. Owing to favourable host‐guest size‐complementarity, the receptor was found to be selective for azide over a diverse range of anions with different geometries. Voltammetric studies revealed the unique ability of the XB ferrocene receptor to selectively sense azide via a significant cathodic shift of its ferrocene/ferrocenium redox couple. Notably, much weaker binding of azide was observed for the hydrogen bonding 1,3‐bis‐prototriazole ferrocene receptor analogue, which also displayed a poorer electrochemical response, suggesting that halogen bonding interactions play crucial roles in the binding and sensing of azide.