In:
European Journal of Organic Chemistry, Wiley, Vol. 2010, No. 6 ( 2010-02), p. 1037-1045
Abstract:
The first water‐soluble C 3 v ‐symmetrical trannulene derivatives of fluorofullerene C 60 F 18 possessing six carboxylic or ammonium ion groups have been synthesized and spectrally characterized. The stability of emerald‐green aqueous solutions of these compounds was investigated. A novel synthetic route was developed for a step‐by‐step derivatization of C 60 F 18 with different organic C–H acids that yielded nonsymmetrically substituted C 60 F 15 R 2 R′ trannulenes. The synthesized trannulenes were loaded with polar carboxylic groups that improved greatly the solubility of these compounds in aqueous media. We showed that four solubilizing COOH groups could be introduced onto the fullerene cage of C 60 F 15 R 2 R′ trannulenes with R substituents and then some additional organic functionality could be attached independently with R′. The R′ substituent might potentially comprise a ligand responsible for selective targeting of the whole trannulene molecule to some specific tissues or intracellular structures. The demonstrated loading of the fluorofullerene core with polar carboxylic or ammonium groups might be considered as an important step towards the design of sophisticated water‐soluble trannulene‐based assembles for biomedical applications.
Type of Medium:
Online Resource
ISSN:
1434-193X
,
1099-0690
DOI:
10.1002/ejoc.v2010:6
DOI:
10.1002/ejoc.200901169
Language:
English
Publisher:
Wiley
Publication Date:
2010
detail.hit.zdb_id:
1475010-7
