We report on the very facile access of a new family of amphiphilic and bola-amphiphilic fullerene [5:1]hexakisadducts 9a-f and 11a-e. The key point for this successful approach is the use of C(2v)-symmetrical fullerene pentakisadduct precursors 2b-f allowing for the completely regioselective addition of a sixth malonate addend to complete the octahedral [5:1] addition pattern. For the synthesis of the new amphiphiles we first developed a new second-generation dendrimer containing 9 tert-butoxycarbonyl (Boc)-protected amino functions at the periphery and two new malonates containing 6 or 18 Boc-protected amino termini, respectively.
View Article and Find Full Text PDFA new approach to creating noncovalent charge transfer ensembles is described. It is based on two components that are linked through anion-receptor interactions. The first component is sapphyrin, a pentapyrrolic expanded porphyrin, which is capable of carboxylate anion recognition and more importantly can act as a photodonor when irradiated in the presence of a suitable electron acceptor.
View Article and Find Full Text PDFThe assembly and degradation behavior of oligoelectrolyte multilayer films (OEMs) self assembled by layer-by-layer deposition of positively and negatively charged oligoelectrolytes 1-6 was investigated. Next to colorless oligoelectrolytes we have employed representatives involving chromophores, in particular porphyrins. This allows for the systematic observation of both assembly and disassembly of the OEMs using optical spectroscopy, where chromophore containing building blocks serve as reporter electrolytes.
View Article and Find Full Text PDFThe chromatographic separation of a highly water-soluble dendritic monoadduct methano[60]fullerene octadecaacid (dendrofullerene) with octadecylsilica bonded phases has been studied. It has been found that the RP-HPLC behavior of this dendrofullerene obeys the general rules of stationary-phase and mobile-phase selection for controlling the separation of usually acidic compounds. An RP-HPLC-ESI-MS analysis confirms the identity of the dendrofullerene and allows characterization of the molecular weights of the main impurities contained in the sample.
View Article and Find Full Text PDFTwo dendritic fullerene (DF) monoadducts, 2 and 3, which can carry up to 9 and 18 negative charges, respectively, were examined with respect to electrostatic complexation with Cytochrome c (Cytc). To facilitate comprehensive photophysical investigations, the zinc analogue of Cytc (ZnCytc) was prepared according to a novel, modified procedure. The association of ZnCytc and DF, and consequential photoinduced electron transfer within ZnCytc-DF from the photoexcited protein to the fullerene, was proven by fluorescence spectroscopy and transient absorption spectroscopy.
View Article and Find Full Text PDFThe aim of the present study was to develop an analytical method for measuring amounts of a dendro[60]fullerene (DF) which is a highly water-soluble [60]fullerene derivative. We tried to define a straightforward methodology using capillary zone electrophoresis, a method which, to our knowledge, has not yet been used to that purpose. Preliminary assays showed that DF has almost the same mobility than the electroosmotic flow (EOF) but in the opposite direction.
View Article and Find Full Text PDFUsing pulse radiolysis and laser flash photolysis, we have investigated the reactions of the deleterious species, e(-)(aq), HO&z.rad;, O(2)(*)(-) and O(2)((1)Delta(g)) with 10 water-soluble cyclopropyl-fused C(60) derivatives including a mono-adduct dendro[60]fullerene (d) and C(60) derivatives based on C(60)[C(COOH)(2)](n=2-6), some of which are known to be neuroprotective in vivo. The rate constants for reactions of e(-)(aq) and HO&z.
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