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Synthesis of Dendritic Branches with Peripheral Fullerene Subunits
Author(s) -
Hahn Uwe,
Hosomizu Kohei,
Imahori Hiroshi,
Nierengarten JeanFrançois
Publication year - 2006
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.200500653
Subject(s) - chemistry , moiety , dendrimer , derivative (finance) , sequence (biology) , fullerene , stereochemistry , alcohol , cleavage (geology) , convergent synthesis , polymer chemistry , organic chemistry , biochemistry , geotechnical engineering , fracture (geology) , financial economics , engineering , economics
Highly soluble dendritic branches with two, four, eight or 16 methanofullerene subunits at their peripheries and carboxylic acid functions at their focal points have been prepared by a convergent approach. Starting from a methanofullerene derivative possessing a tert ‐butyl ester function, the successive dendrimer generations were obtained by repetition of a reaction sequence involving cleavage of the tert ‐butyl ester moiety under acidic conditions, followed by a DCC‐mediated esterification reaction with an A 2 B building block possessing two benzylic alcohol functions and a tert ‐butyl ester group. This repetitive synthetic sequence is very efficient and allowed the dendritic growth up to the fifth‐generation derivative, containing 16 peripheral fullerene subunits. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)