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Synthesis and Covalent Grafting of Tripod‐Shaped Oligo( p ‐phenylene)s End‐Capped with Azide Groups
Author(s) -
SánchezMolina María,
LópezRomero Juan M.,
HierrezueloLeón Jesús,
MartínRufián Mercedes,
Díaz Amelia,
Valpuesta María,
ContrerasCáceres Rafael
Publication year - 2016
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201500526
Subject(s) - chemistry , tripod (photography) , azide , phenylene , alkyne , covalent bond , cycloaddition , polymer chemistry , click chemistry , molecule , combinatorial chemistry , organic chemistry , catalysis , physics , optics , polymer
Here we report the synthesis and characterization of several tripod‐shaped oligo( p ‐phenylene)s molecules with legs composed of five and three phenylene units, compounds 1 and 2 , respectively. In these structures, each leg is end‐capped with an azide group and the terminal functional arm contains an acetylene or bromine group. The presented synthesis has as the key step a Pd‐catalyzed Suzuki cross‐coupling reaction. In particular, the iodine derivative from the silicon core molecule reacts with the appropriate oligo( p ‐phenylene) boron derivative, thus generating the final tripod‐shaped structure. The azide end‐capped leg is specifically designed for its covalent incorporation on alkynyl terminated silicon surfaces in an easy and reproducible way. As a preliminary study, we present the nanostructuration of tripod 2 a on alkynyl‐functionalized silicon wafers through copper‐catalyzed alkyne‐azide cycloaddition (CuAAC) click reaction.