Synthesis of dipyrrolic species for direct preparation of mesosubstituted chlorines
Abstract
A dipyrrolic structures were synthesised for direct preparation of asymmetrically functionalized chlorin macrocycles
About the Authors
N. V. Konovalova
M.V. Lomonosov Moscow State University of Fine Chemical Technologies, 86, Vernadskogo pr., Moscow 119571
Russian Federation
Russian Federation
O. V. Motova
M.V. Lomonosov Moscow State University of Fine Chemical Technologies, 86, Vernadskogo pr., Moscow 119571
Russian Federation
Russian Federation
References
1. Коновалова, Н. В. Синтетические молекулярные системы на основе порфиринов как модели для изучения переноса энергии при фотосинтезе / Н. В. Коновалова, Р. П. Евстигнеева, В. Н. Лузгина // Успехи химии. - 2001. - Т. 70, № 11. - С. 1059-1093.
2. D'Souza, F. Photoinduced electron transfer in supramolecular systems of fullerenes functionalized with ligands capable of binding zinc porphyrins and zinc phthalocyanines / F. D'Souza, O. Ito // Coord. Chem. Rev. - 2005. - Vol. 249. - P. 1410-1422.
3. Burrell, A. K. Porphyrin-based nanostructures: routes to molecular electronics / A. K. Burrell, M. R. Wasielewski // J. Porphyrins Phthalocyanines. - 2000. - Vol. 4, № 4. - P. 401-406.
4. Gust, D. Molecular mimicry of photosynthetic energy and electron transfer / D. Gust, T. A. Moore, A. L. Moore // Acc. Chem. Res. - 1993. - Vol. 26. - P. 198-205.
5. Osuka, A. A chemical approach towards the photosynthetic reaction center / A. Osuka, N. Mataga, T. Okada // Pure Appl. Chem. - 1997. - Vol. 69, № 4. - P. 797-802.
6. Fukuzumi, S. Bioinspired electron-transfer systems and applications / S. Fukuzumi // Bull. Chem. Soc. Jpn. - 2006. - Vol. 79, № 2. - P. 177-195.
7. Imahori, H. Porphyrin-fullerene linked systems as artificial photosynthetic mimics / H. Imahori // Org. Biomol. Chem. - 2004. - Vol. 2. - P. 1425-1433.
8. Schuster, D. I. Porphyrin-fullerene photosynthetic model systems with rotaxane and catenane architectures / D. I. Schuster, K. Li, D. M. Guldi // C. R. Chimie. - 2006. - Vol. 9. - P. 892-908.
9. Jiang, L. The progress on design and synthesis of photoactive porphyrin-based dyads, triad and polymers / L. Jiang, Y. Li // J. Porphyrins Phthalocyanines. - 2007. - Vol. 11, № 5-6. - P. 299-312.
10. Rational synthesis of meso-substituted chlorin building blocks / J.-P. Strachan, D. F. O'Shea, T. Balasubramanian, J. S. Lindsey // J. Org. Chem. - 2000. - Vol. 65, № 10. - P. 3160-3172.
11. Battersby, A. R. Synthetic studies relevant to biosynthetic research on vitamin B12. Part 7. Synthesis of (±)-Bonellin dimethyl ester / A. R. Battersby, C. J. Dutton, C. J. R. Fookes // J. Chem. Soc., Perkin Trans. 1. - 1988. - P. 1569-1576.
12. Refined synthesis of 5-substituted dipyrromethanes / B. J. Littler [et al.] // J. Org. Chem. - 1999. - Vol. 64. - P. 1391-1396.
13. Efficient synthesis of monoacyl dipyrromethanes and their use in the preparation of sterically unhindered trans-porphyrins / P. D. Rao [et al.] // J. Org. Chem. - 2000. - Vol. 65. - P. 1084-1092.
14. Беллами, Л. Инфракрасные спектры молекул / Л. Беллами. - М.: Изд-во иностранной литературы, 1957. - 444 с.
15. Наканиси, К. Инфракрасные спектры и строение органических соединений / К. Наканиси. - М. : Мир, 1965. - 165 c.
16. Synthetic approaches to regioisomerically pure porphyrins bearing four different meso-substituents / C.-H. Lee [et al.] // Tetrahedron. - 1995. - Vol. 51, № 43. - P. 11645-11672.
17. Общая органическая химия. Т. 6. / Ред. Н. К. Кочетков, Ю. Н. Бубнов. - М. : Химия, 1984. - 329 c.
18. Shechter, H. Nitroalkane from conjugated nitroalkenes by reduction with complex hydrides / H. Shechter, D. E. Ley, E. B. Roberson // J. Am. Chem. Soc. - 1956. - Vol. 78. - P. 4984-4989.
19. Преч, Э. Определение строения органических соединений. Таблицы спектральных данных / Э. Преч, Ф. Бюльманн, К. Аффольтер. - М.: Мир; БИНОМ. Лаборатория знаний, 2006. - 438 с.
20. Synthesis of meso-substituted chlorines via tetrahydrobilene-a intermediates / M. Taniguchi [et al.] // J. Org. Chem. - 2001. - Vol. 66. - P. 7342-7354.
Review
For citations:
Konovalova N.V., Motova O.V. Synthesis of dipyrrolic species for direct preparation of mesosubstituted chlorines. Fine Chemical Technologies. 2008;3(6):34-44. (In Russ.)
Views:
369
Email this article 
