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Facile Access to Functional Building Blocks of C 60 Involving C 3 ‐Symmetrical Addition Patterns
Author(s) -
Gmehling Alexander,
Hirsch Andreas
Publication year - 2013
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.201300482
Subject(s) - chemistry , moiety , block (permutation group theory) , bromide , stereochemistry , benzyl bromide , porphyrin , organic chemistry , combinatorics , mathematics , catalysis
A new class of C 3 ‐symmetrical fullerene building blocks with a well‐defined spatial arrangement of addends has been developed. They comprise compounds with a e , e , e ‐trisaddition pattern and a mixed octahedral hexakisaddition pattern. Fullerenophosphates with a e,e,e ‐addition pattern were used for the spatial preorganization of the addends. After deprotection seven different trisbromides ( 12 – 16 , 15a , 16a ) with varying chain lengths and orientation of the functional groups were obtained. Acetylenes could be coupled to these compounds by click chemistry through an intermediate trisazide. For the synthesis of mixed hexakisadducts 19 – 21 a template system based on a central benzyl moiety was attached to the free hemisphere of the trisadduct fullerenophosphates. It was shown that the phosphate and the benzyl template can be removed independently. Fully deprotected building block 24 bearing both terminal bromide and hydroxy moieties was prepared. In addition, rather complex hybrid architecture 29 bearing three porphyrin units in the polar addend zone was successfully synthesized.