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Synthesis of a Calix[4]arene‐Monodiazonium Salt for Surface Modification
Author(s) -
Malytskyi Volodymyr,
TroianGautier Ludovic,
Mattiuzzi Alice,
Lambotte Sarah,
Cornelio Benedetta,
Lagrost Corinne,
Jabin Ivan
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801253
Subject(s) - calixarene , redox , covalent bond , electrochemistry , surface modification , glassy carbon , monolayer , chemistry , salt (chemistry) , carbon fibers , polymer chemistry , diazonium compounds , combinatorial chemistry , inorganic chemistry , electrode , organic chemistry , materials science , cyclic voltammetry , molecule , biochemistry , composite material , composite number
Reduction of calix[4]arene‐tetradiazonium salts at the vicinity of a surface, notably a carbon surface, leads to the formation of a dense and robust covalently bound monolayer. To expand the versatility of this unique methodology, the efficient synthesis of a calix[4]arene bearing a single diazonium group and thus a single anchoring point was achieved. The introduction of the diazonium group was developed through an original approach involving a copper‐catalyzed reaction for the preparation of an intermediate azido‐calixarene. The grafting ability of the calix[4]arene‐monodiazonium cation was evaluated by investigating its electrochemical reduction at glassy carbon electrodes. Studies of the blocking properties of the modified surfaces toward redox probes evidenced the formation of compact covalently bound layers at the carbon substrates, opening interesting perspectives in the field of surface modification by calixarene‐based diazonium salts.