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Dendritic Mixed Hexakisadducts of C 60 with a T h Symmetrical Addition Pattern
Author(s) -
Herzog Andrea,
Hirsch Andreas,
Vostrowsky Otto
Publication year - 2000
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/(sici)1099-0690(200001)2000:1<171::aid-ejoc171>3.0.co;2-b
Subject(s) - chemistry , fullerene , stereochemistry , organic chemistry
The synthesis and complete characterization of dendritic hexakisadducts 8‐13 of C 60 with a mixed (1:5, 2:4, 3:3 and 4:2) T h symmetrical addition pattern is described. Pentakis‐, tetrakis‐, tris‐ and bisadducts 4‐7 of C 60 with diethyl malonate addends arranged in an incomplete octahedral addition pattern served as core building blocks. Completion of the pseudo‐octahedral architecture was achieved by exhaustive cyclopropanation with first‐ to third‐generation bromomalonate dendra 1‐3 consisting of the corresponding Fréchet‐type 3,5‐dihydroxybenzyl alcohol subunits. This concept allows for the convergent synthesis of globular dendrimers with a variable number of dendritic malonates (1‐4) and a high dendron density in good yields. The 1 H and 13 C NMR spectra reflect the T h symmetrical addition pattern of the products and reveal spatial interactions of inner dendron branches.