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In recent time the functionally substituted fullerenes are of the particular interest; a large number of publications in the world literature is devoted to the synthesis and study of these compounds.[1-10] Fullerene derivatives have valuable properties and can find practical application in various fields of science and technology as a new chromatographic carriers, liquid crystals, catalysts, dyes, superfirm composites, various conductors, molecular ferromagnets.[1] Application of water-soluble derivatives of fullerene in medicine is rather perspective.[2] Electron donors such as porphyrin, ferrocene, N,N-dimethylaminophenyl, ruthenium(II) trisbipyridine and tetrathiafulvarene, phtalocyanines and others[3-10] have been employed to form fullerene electron donor type dyads and also can find application in photovoltaic. Since fullerenes linked to porphyrins can produce a long-lived chargeseparated state with a high quantum yield in comparison with other known types of donor-acceptor complexes, they are useful candidates to build molecular and supramolecular devices and artificial light energy harvesting systems with unique electronic and magnetic properties.[1,12] One of the most quickly developing directions is connected with the synthesis and study of fullerenecontaining thermotropic liquid crystals (LC) a new class of nanostructured materials. C60 does not behave as a mesogenic unit. Two approaches have been developed for the preparation of fullerene-containing liquid crystalline derivatives: in the first one (covalent approach),[13-19] C60 is functionalized with liquid crystalline addends, whereas in the second one (non-covalent approach),[20-21] a supramolecular complex is formed between C60 and mesogenic fragments. It was shown that mesomorphic derivatives of porphyrins can be chosen as mesogenic fragments.[2,22] To the beginning of our research the conjugates on the basis of covalent-associated conjugates of fullerene C60 and mesogenic porphyrins have not been described in the literature. The present work is devoted to the synthesis of porphyrin-fullerene conjugates based on the fullerene C60 and previously obtained meso-arylsubstituted porphyrins containing long chain alkyl groups. Conjugates 4, 5 were obtained by the method of Prato.[2] Formylporphyrins with long alkyl substituents were used as aldehyde components. The meso-arylsubstituted porphyrin 1 was synthesized by the monopyrrole condensation method in soft conditions using pyrrole and 4-tetradecyloxybenzaldehyde with 40 % yield.[23] Based on the compound 1 Ni and Cu complexes were obtained (Scheme 1). Formylporphyrins 2, 3 were synthesized by the Vilsmeier method using DMF and POCl3 in CHCl3 during 5-6 h, t = 60°C. The structure of Ni and Cu complexes of 2-formyl5,10,15,20–tetrakis-(p-tetradecyloxyphenyl)porphyrin (2, 3) was determined by 1H NMR, IR, UV-vis spectroscopy

Synthesis of Conjugates Based on Fullerene C60 and meso-Tetraphenyl­porphyrins with Long Chain Substituents

Synthesis of Conjugates Based on Fullerene C60 and meso-Tetraphenylporphyrins with Long Chain Substituents