Fullerenes conjugation

H. Kato, N. Kaneta, S. Nii, K. Kobayashi, N. Fukui, H. Shinohara, and Y. Nishida, Preparation and supramolecular properties of unadulterated glyco-syl liposomes from a bis(a-D-mannopyranosyl)-[60]fullerene conjugate, Chem. Biodivers., 2 (2005) 1232-1241. 

Filippone, S., Heimann, F., and Rassat, A. (2002) A highly water-soluble 2 1 beta-cyclodextrin-fullerene conjugate. Chem. Comm., 1508-1509. 

Hirayama J, Abe H, Kamo N, Shinbo T, Ohnishi-Yamada Y, Kurosawa S, Ikebuchi K, Sekiguchi S (1999) Photoinactivation of vesicular stomatitis virus with fullerene conjugated with methoxy polyethylene glycol amine. Biol Pharm Bull 22 1106-1109. 

D Souza E, Maligaspe E, Ohkubo K et al (2009) Photosynthetic reaction center mimicry low reorganization energy driven charge stabilization in self-assembled cofacial zinc phthalocy-anine dimer-fullerene conjugate. J Am Chem Soc 131 8787-8797... 

In terms of the Dewar-Chatt model of bonding, for v metal complexation one double bond is effectively removed from the fullerene conjugation system due to extensive interaction between metal d orbitals and the fullerene HOMO and LUMO (7). The remaining 29 double bonds then behave almost identically to uncomplexed C60 with their IR, Raman, UV-vis, and 13C NMR spectra showing only slight perturbations, mainly as a result of diminution of symmetry effects. Nevertheless, it is important to state that the fullerene metal interaction is not confined purely to the former s HOMO and LUMO, and that other molecular orbitals are energetically suitable for interaction 89,90). The spectroscopic evidence cited for the preceding statement is as follows ... 

More recently, another example of a Pc-based system (31) (Fig. 27a) able to self-organize on HOPG and graphite-like surfaces by drop-casting technique was reported. AFM studies revealed that the covalently linked Pc-C6o fullerene conjugate 31 is able to form nanostructured fibers and films (Fig. 27b) [48],... 

Figure 7.52. Schematic of a PAMAM dendrimer-fullerene conjugate structure (top), with TGA analysis (bottom). Based on the mass loss of the conjugate, it is suggested that each PAMAM dendrimer is surrounded by 30 fullerene units. Reproduced with permission from Jensen, A. W. Maru, B. S. Zhang, X. Mohanty, D. K. Fahlman, B. D. Swanson, D. R. TomaUa, D. A. Nano Lett. 2005, 5, 1171. Copyright 2005 American Chemical Society.

Porphyrin-fullerene conjugates attract wide attention for their intramolecular energy and electron transfer properties [87, 88]. By attachment of the porphyrin to two points on the Cgo surface, the interchromophoric spatial relationship in the cyclophane-type molecular dyads trans-2 ( )-52 [67] and trans-1 54 [68] (Scheme 7-8), which controls both energy and electron transfer, is rigorously defined. In the two systems, as well as in the fullerene-porphyrin conjugate 58 [75] (Scheme 7-9), the close proximity between fullerene and porphyrin chromophore leads to a nearly complete quenching of the porphyrin luminescence, presumably as a result of efficient energy transfer between the porphyrin donor and the fullerene acceptor. 

Brabec, C.J., F. Padinger, J.C. Hummelen, R.A.J. Janssen, and N.S. Sariciftci. 1999. Realization of large area flexible fullerene-conjugated polymer photocells A route to plastic solar cells. Synth Met 102 861. 

Fullerene/Conjugated Polymer Composite for the State-of-the-Art Polymer Solar Cells... 

Matsuo Y, Tahara K, Sawamura M, Nakamura E (2004) Creation of hoop- and bowl-shaped benzenoid systems by selective detraction of [60]fullerene conjugation. [lOJCyclophenacene and fused corarmulene derivatives. J Am Chem Soc 126(28) 8725-8734... 

Souza FD, Chitta R, Gadde S, McCarty AL, Karr PA, Zandler ME, Sandanayaka ASD, Araki Y, Ito O (2006) Design, syntheses and studies of supramolecular porphyrin-fullerene conjugates, using bis-18-crown-6 appended porphyrins and pyridine or alkyl ammonium fiuictionalized fullerenes. J Phys Chem B 110 5905-5913... 

Scheme 51 Synthesis of fullerene conjugate with perfluorinated subphthalocyanine...

Scheme 54 Synthesis of trifluoroethoxy-coated subphthalocyanine and its fullerene conjugate...

Nierengarten JF, Oswald L, Nicoud JF (1998) Dynamic cis/trans isomerisation in a porphyrin-fullerene conjugate. Chem Commun 15 1545-1546... 

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