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Donor-acceptor systems based on fullerene C60 and lipophilic meso-arylporphyrins

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Abstract

In this paper we report the synthesis donor - acceptor systems based on fullerene C60 and lipophilic meso - arylporphyrins . The obtained conjugates were characterized by IR, UV-vis,1H,13C NMR spectroscopy and MALDI-TOF mass spectrometry. The fluorescence spectra of porphyrin–fullerene C60 donor-acceptor dyads were studied.

About the Authors

E. S. Zyablikova
МИТХТ им. М.В. Ломоносова
Russian Federation


N. A. Bragina
МИТХТ им. М.В. Ломоносова
Russian Federation


A. F. Mironov
МИТХТ им. М.В. Ломоносова
Russian Federation


References

1. Langa F. Fullerenes Principles and Applications. – Cambridge: The Royal Society of Chemistry, 2007. 398 p.

2. Durdagi S., Supuran C.T., Strom T.A. In silico drug screening approach for the design of magic bullets: A successful example with anti-HIV fullerene derivatized amino acids // J. Chem. Inf. Model. 2009. V. 49. Р. 1139–1143.

3. Rezayat S.M., Boushehri S.V.S., Salmanian B. The porphyrin–fullerene nanoparticles to promote the ATP overproduction in myocardium: 25Mg2+-magnetic isotope effect // Eur. J. Med. Chem. 2009. V. 44. № 4. P. 1554–1569.

4. Kharisov B.I. Recent advances in the synthesis, characterization, and applications of fulleropyrrolidines // Ind. Eng. Chem. Res. 2009. V. 48. P. 545–571.

5. D’Souza F., Chitta R., Ohkubo K. Corrole–fullerene dyads: Formation of long-lived charge-separated states in nonpolar solvents // J. Am. Chem. Soc. 2008. V. 130. P. 14263–14272.

6. Lee J.-C., Kim T.-Y., Kang S.H., Shim Y.K. Synthesis of covalently linked chlorin–fullerene dyads // Bull. Korean Chem. Soc. 2001. V. 22. № 3. P. 257–258.

7. Meijer M.D. Metal-chelating capacities attached to fullerenes // Coord. Chem. Rev. 2002. V. 230. P. 141–163.

8. Schuster D.I., Li K., Guldi D.M. Porphyrin–fullerene photosynthetic model systems with rotaxane and catenane architectures // C. R. Chimie. 2006. V. 9. P. 892–908.

9. Алексеев А.С., Ткаченко Н.В., Ефимов А.В., Лемметюйнен Х. Фотоиндуцированный направленный перенос электрона в многослойных пленках Ленгмюра–Блоджетт производных порфирина и фталоцианина // Журн. физ. хим. 2010. T. 84. № 7. C. 1356–1367.

10. Rosen B.M., Wilson C.J., Wilson D.A. Dendron-mediated self-assembly, disassembly, and self-organization of complex systems. // Chem. Rev. 2009. V. 109. P. 6275–6540.

11. Lenoble J., Maringa N., Campidelli S. Liquid-crystalline fullerodendrimers which display columnar phases // Org. Lett. 2006. V. 8. P. 1851–1854.

12. Campidelli S., Milic D., Lenoble J. Liquid-crystalline bisadducts of [60]fullerene // Tetrahedron. 2006. V. 62. P. 2115–2122.

13. Li W.-S., Yohei Y., Takanori F., Akinori S., Shu S. Amphiphilic molecular design as a rational strategy for tailoring bicontinuous electron donor and acceptor arrays: Photoconductive liquid crystalline oligothiophene-C60 dyads // J. Am. Chem. Soc. 2008. V. 130. P. 8886–8887.

14. Nakanishi T., Shen Y., Wang J., Yagai S., Funahashi M., Kato T., Fernandes P., Mohwald H., Kurth D. G. Electron transport and electrochemistry of mesomorphic fullerenes with long-range ordered lamellae // J. Am. Chem. Soc. 2008. V. 130. P. 9236–9237.

15. Escosura A., Martınez-Dıaz M.V., Barbera J., Torres T. Self-organization of phthalocyanine–[60]fullerene dyads in liquid crystals // J. Org. Chem. 2008. V. 73. P. 1475–1480.

16. Li Q. Self-organized organic semiconductors: From materials to device applications. – US: John Wiley and Sons, 2011. 320 p.

17. Ohta K., Yamaguchi N., Yamamoto I. Discotic liquid crystals of transition metal complex. Synthesis and mesomorphism of porphyrin derivaties substituted with two or four bulky groups // J. Mater. Chem. 1998. V. 8. P. 2637–2650.

18. Wei L., Tong-Shun S. Properties of meso-tetrakis(4-n-alkanoyloxyphenyl)porphyrin liquid crystal Co and Ni complexes // Science in China. 2007. V. 50. P. 488–493.

19. Брагина Н.А., Федулова И.Н., Новиков Н.В., Крутикова Е.С., Миронов А.Ф., Быкова В.В., Ананьева Г.А., Усольцева Н.В. Синтез и мезогенные свойства липофильных и амфифильных тетрафенил-порфиринов // Macroheterocycles. 2009. Т. 2. № 3-4. С. 228–236.

20. Sandanayaka A.S.D., Murakami T., Hasob T. Chiroselective assembly of a chiral porphyrin–fullerene dyad: Photoconductive nanofiber with a top-class ambipolar charge-carrier mobility // J. Phys. Chem. C. 2009. V. 113. P. 18369–18378.

21. Fedulova I.N., Bragina N.A., Novikov N.V., Ugol’nikova O.A., Mironov A.F. Synthesis of lipophilic tetraphenylporphyrins to design lipid–porphyrin ensembles // Rus. J. Bioorg. Chem. 2007. V. 33. № 6. P. 635–639.

22. Brockmann H.J., Bliesener K.M., Inhoffen H.H. Zur weiteren kenntis des chlorophylls und des hemins // Liebigs Ann. Chem. 1968. V. 718. P. 148–161.

23. Москальчук Т.В. Изучение реакции формилирования в ряду мезо-тетраарилзамещенных порфиринов и хлоринов: дис. … канд. хим. наук. – М., 2004. 125 с.

24. Buchler J.VW., Dreher C., Herget G. Vilsmeier-formylierung von metalloporphyrinen mit CoII, NiII, PdII, PtII, CuII, ZnII, CoIII, CrIII, MnIII, FeIII, AlIII, SiIV und PtIV in abhangigkeit vom zentralmetall // Liebigs Ann. Chem. 1988. V. 1988. № 1. P. 43–54.

25. Маравин Г.Б., Пономарев Г.В., Яшунский Д.В., Морлян Н.М. Способ получения 1-формил-α,β,γ,δ-тетрафенилпорфирина: А.с. 891673 (СССР). Опубл. 1981, Б.И. № 47. С. 109.

26. Maggini M., Scorrano G., Prato M. Addition of azomethine ylides to C60: Synthesis, characterization, and functionalization of fullerene pyrrolidines // J. Am. Chem. Soc. 1993. V. 115. P. 9798–9799.

27. Drovetskaya T., Reed C.A., Boyd P. A fullerene porphyrin conjugate // Tetrahedron Lett. 1995. V. 36. P. 7971–7974.

28. Ma B., Sun Y.-P. Fluorescence spectra and quantum yields of [60]fullerene and [70] fullerene under different solvent conditions. A quantitative examination using a near-infrared-sensitive emission spectrometer // J. Chem. Sос., Perkin Trans. 1996. V. 2. Р. 2157–2162.


For citation:


Zyablikova E.S., Bragina N.A., Mironov A.F. Donor-acceptor systems based on fullerene C60 and lipophilic meso-arylporphyrins. Fine Chemical Technologies. 2012;7(5):28-33. (In Russ.)

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