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New Polyalkynyl Dendrons and Dendrimers: “Click” Chemistry with Azidomethylferrocene and Specific Anion and Cation Electrochemical Sensing Properties of the 1,2,3‐Triazole‐Containing Dendrimers
Author(s) -
Camponovo Jérémy,
Ruiz Jaime,
Cloutet Eric,
Astruc Didier
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200801999
Subject(s) - dendrimer , click chemistry , chemistry , ferrocene , electrochemistry , combinatorial chemistry , triazole , polymer chemistry , catenane , electrode , organic chemistry , molecule
Dendrimers for ion sensing : The synthesis and use of new tris‐alkynyl dendrons are reported. So‐called “click” reactions of the dendrimers described with azidomethylferrocene give 27‐ferrocenyl, 81‐ferrocenyl, and 243‐ferrocenyl dendrimers. Electrochemical recognition of oxo‐anions and Pd 2+ cations has been compared using the three polyferrocenyl dendrimers.The synthesis and use of the new tris‐alkynyl dendrons 2 to 5 are reported, including the Williamson reaction of 5 with 9‐iodo ( 9 ), 27‐iodo ( 11 ), and 81‐iodo ( 12 ) dendritic cores to yield 27‐alkynyl ( 13 ), 81‐alkynyl ( 14 ), and 243‐alkynyl ( 15 ) dendrimers. So‐called “click” reactions of these three dendrimers with azidomethylferrocene ( 20 ) give 27‐ferrocenyl ( 16 ), 81‐ferrocenyl ( 17 ), and 243‐ferrocenyl ( 18 ) dendrimers. Electrochemical recognition of oxo‐anions (H 2 PO 4 − and ATP 2− ) and Pd 2+ cation has been compared using the three polyferrocenyl dendrimers. Derivatization of Pt electrodes with the dendrimers for recognition becomes more facile with increasing size of the dendrimer. This first “click” dendrimer bearing 243‐ferrocenyl groups is the best one in the series to obtain robust, recyclable modified Pt electrodes, whereas previous “click” ferrocenyl dendrimers have not been suitable for this purpose.