Ulleren-3-yl)indolin-2-one (AIM 1) was synthesized in accordance with ref. [7]. Isatins A 2 have been obtained by known procedures [11-14]. The basic process for synthesis of 1-alkyl-3-(3-cyclopropane[1,9](C60-Ih)[5,6]fulleren-3-yl)-indolin-2-one (AIMs 2) was as follows: tris(diethylamino)phosphine (0.1 g, 0.4 mmol) was added dropwise to a mixture on the corresponding isatins A two (0.14 mmol) and C60 (0.1 g, 0.14 mmol) in anhydrous o-dichlorobenzene (40 mL) at 0 The mixture was stirred for 8 h at 0 and then the temperature was allowed to rise to area temperature. The solvent was removed below decreased pressure and also the residue was purified by column chromatography on silica gel using a mixture of toluene and petroleum ether 4:five as eluent. Soon after elution with the recovered C60, the fraction containing the desired compound was collected and dried in vacuo at 300 for 6 h. Analytical information of these compounds can be found in Supporting Details File 1.Beilstein J. Org. Chem. 2014, 10, 1121128.The devices had been illuminated by means of a 3.2 mm2 circular aperture, which was in contact with the glass side in the device, by using a 150 W solar simulator (model 9600, Newport) with an AM1.5G filter, the optical power around the sample was set to about one hundred mW/cm2 together with the assist of a bolometric detector. Atomic force microscopy (AFM) pictures on the polymer-fulllerene blended films were recorded having a Smena instrument (NTMDT) in the tapping mode.11. Shmidt, M. S.; Reverdito, A. M.; Kremenchuzky, L.; Perillo, I. A.; Blanco, M. M. Molecules 2008, 13, 83140. doi:ten.3390/molecules13040831 12. Diaz, P.; Xu, J.; Astruc-Diaz, F.; Pan, H.-M.; Brown, D.Losmapimod L.; Naguib, M. J. Med. Chem. 2008, 51, 4932947. doi:ten.1021/jm8002203 13. Shimazawa, R.; Kuriyama, M.; Shirai, R. Bioorg. Med. Chem. Lett. 2008, 18, 3350353. doi:10.1016/j.bmcl.2008.04.027 14. Tacconi, G.; Righetti, P. P.; Desimoni, G. J. Prakt. Chem. 1973, 315, 33944. doi:ten.1002/prac.19733150221 15. Farnia, G.; Capobianco, G.; Romanin, A. J. Electroanal. Chem. 1973, 45, 39704. doi:ten.1016/S0022-0728(73)80049-X 16. Troshin, P. A.; Hoppe, H.; Renz, J.; Egginger, M.; Mayorova, J. Y.; Goryachev, A. E.; Peregudov, A. S.; Lyubovskaya, R. N.; Gobsch, G.; Sariciftci, N. S.; Razumov, V. F. Adv. Funct. Mater. 2009, 19, 77988. doi:10.1002/adfm.200801189 17. Tsoi, W. C.; James, D. T.; Kim, J. S.; Nicholson, P.Ganglioside GM3 G.PMID:23695992 ; Murphy, C. E.; Bradley, D. D. C.; Nelson, J.; Kim, J.-S. J. Am. Chem. Soc. 2011, 133, 9834843. doi:ten.1021/ja2013104 18. Mihailetchi, V. D.; Xie, H. X.; De Boer, B.; Koster, L. J. A.; Blom, P. W. M. Adv. Funct. Mater. 2006, 16, 69908.Supporting InformationSupporting Info FileAnalytical data of AIM two. [http://www.beilstein-journals.org/bjoc/content/ supplementary/1860-5397-10-111-S1.pdf]AcknowledgementsThe support by the Russian foundation for Fundamental Analysis (grants 12-03-00164-, 11-02-90732-mob-st) and by the System No. six of your Division of Chemistry and Material Sciences of Russian Academy of Sciences is gratefully acknowledged.doi:ten.1002/adfm.200500420 19. Cook, S.; Ohkita, H.; Kim, Y.; Benson-Smith, J. J.; Bradley, D. D. C.; Durrant, J. R. Chem. Phys. Lett. 2007, 445, 27680. doi:ten.1016/j.cplett.2007.08.005 20. Blom, P. W. M.; Mihailetchi, V. D.; Koster, L. J. A.; Markov, D. E. Adv. Mater. 2007, 19, 1551566. doi:ten.1002/adma.200601093 21. Ye, G.; Chen, S.; Xiao, Z.; Zuo, Q.; Wei, Q.; Ding, L. J. Mater. Chem. 2012, 22, 223742377. doi:ten.1039/c2jm35247h
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