Synthesis, Electrochemistry and Optical Limiting Properties of Spirobifluorene-fulleropyrrolidine Derivatives

Abstract

Abstract: Three novel fullerene(C₆₀/C₇₀) derivatives containing spirobifluorene, named 2-(9,9′-spirobi[fluorene]-2-yl)-1-methylfullero[C₇₀]pyrrolidine(6), 2-(9,9′-spirobi[fluorene]-2-yl)-1-methylfullero[C₆₀]pyrrolidine(7) and 2′-(1-methyl- fullero[C₆₀]pyrrolidin-2-yl)-9,9′-spirobi[fluorene]-2-carbaldehyde(8), respectively, were synthesized and their structures were confirmed by IR, ¹H NMR, ¹³C NMR, MALDI-TOF. Their electrochemical properties were studied by cyclic voltammetry. The results show that reduction peaks of C₇₀ derivative 6 shift to more negative than that of C₆₀ derivative 7 about 0.1, 0.12 and 0.01 V, respectively. Their optical limiting properties were investigated by nanosecond and femtosecond laser system. Comparative study on their optical limiting properties indicated that they showed different optical-limiting mechanisms for nanosecond and femtosecond laser. The optical limiting thresholds of 13.7, 15.3 and 23.3 J/cm² in nanosecond timescale were determined for compounds 6—8. The results show that they are effective optical limiters for laser protection.

Key words: Optical-limiting, Spirobifluorene, Fulleropyrrolidine

TrendMD:

LI Cai-Hua, HUO Zhi-Ming, ZENG He-Ping*. Synthesis, Electrochemistry and Optical Limiting Properties of Spirobifluorene-fulleropyrrolidine Derivatives[J]. Chem. J. Chinese Universities, 2010, 31(8): 1554.

References

[1]Kim Y., Cook S., Tuladhar S. M., Choulis S. A., Nelson J., Durrant J. R., Bradley D. D. C., Giles M., McCulloch I., Ha C. S., Ree M.. Nat. Mater.[J], 2006, 5(3): 197—203 [2]Pingree L. S. C., Reid O. G., Ginger D. S.. Nano. Lett.[J], 2009, 9(8): 2946—2952 [3]Yamakoshi Y., Umezawa N., Ryu A., Arakane K., Miyata N., Goda Y., Masumizu T., Nagano T.. J. Am. Chem. Soc.[J], 2003, 125(42): 12803—12809 [4]Tagmatarchis N., Shinohara H.. Med. Chem.[J], 2001, 1(4): 339—348 [5]Tutt L. W., Kost A.. Nature[J], 1992, 356(6366): 225—226 [6]LIU Ying(刘莹), CHEN Yu(陈彧), FENG Miao(冯苗), LING Ying(林楹), Doyle J. J., Blau W. J., CAI Liang-Zhen(蔡良珍). Chem. J. Chinese Universities(高等学校化学学报)[J], 2007, 28(11): 2092—2095 [7]HE Chun-Ying(贺春英), WU Yi-Qun(吴谊群), SONG Ying-Lin(宋瑛林), WANG Yu-Xiao(王玉晓), ZUO Xia(左霞). Chem. J. Chinese Universities(高等学校化学学报)[J], 2003, 24(8): 1360—1365 [8]Felder D., Guillon D., Levy R., Mathis A., Nicoud J. F., Nierengarten J. F., Rehspringer J. L., Schell J.. J. Mater. Chem.[J], 2000, 10(4): 887—892 [9]Tang B. Z., Peng H., Leung S. M., Au C. F., Poon W. H., Chen H., Wu X., Fok M. W., Yu N. T., Hiraoka H., Song C., Fu J., Ge W., Wong G. K. L., Monde T., Nemoto F., Su K. C.. Macromolecules[J], 1998, 31(1): 103—108 [10]TAN Hai-Rong(谭海荣), ZENG He-Ping(曾和平). Chem. J. Chinese Universities(高等学校化学学报)[J], 2009, 30(5): 934—937 [11]Peng H., Lam J. W. Y., Tang B. Z.. Rapid Commun.[J], 2005, 26(9): 673—677 [12]Belfield K. D., Bondar M. V., Hernandez F. E., Przhonska O. V.. J. Phys. Chem. C[J], 2008, 112(14): 5618—5622 [13]Wu R., Schumm J. S., Pearson D. L., Tour J. M.. J. Org. Chem.[J], 1996, 61(20): 6906—6921 [14]Clarkson R. G., Gomberg M.. J. Am. Chem. Soc.[J], 1930, 52: 2881—2891 [15]Poriel C., Ferrand Y., Juillard S., Paul L. M., Simonneaux G.. Tetrahedron[J], 2004, 60(1): 145—158 [16]Mattiello L., Fioravanti G.. Synt. Commun.[J], 2001, 31(17): 2645—2648 [17]Langa F., de la Cruz P., Espildora E., Gonzalez-Cortes A., de la Hoz A., Lopez-Arza V.. J. Org. Chem.[J], 2000, 65(25): 8675—8684 [18]HUO Yan-Ping(霍延平), ZENG He-Ping(曾和平), JIANG Huan-Feng(江焕峰), LIU Jun-Hui(刘军辉), MAO Yan-Li(毛艳丽). Chinese Journal of Organic Chemistry(有机化学)[J], 2006, 26: 1657—1662 [19]Cattarin S., Ceroni P., Guldi D. M., Maggini M., Menna E., Paolucci F., Roffia S., Scorrano G.. J. Mater. Chem.[J], 1999, 9(11): 2743—2750 [20]Zhao Y., Fang Y., Jiang Y.. Spectrochim. Acta A[J], 2006, 64A(3): 564—567 [21]Foley S., Berberan-Santos M. N., Fedorov A., Bensasson R. V., Leach S., Gigante B.. Chem. Phys.[J], 2001, 263(2/3): 437—447 [22]FANG Qing(方晴), ZENG He-Ping(曾和平), ZHANG Wei-Min(张卫民), ZHANG Pei-Quan(张培全). Chinese Journal of Organic Chemistry(有机化学)[J], 2008, 28: 814—818 [23]Zeng H. P., Wang T., Sandanayaka A. S. D., Araki Y., Ito O.. J. Phys. Chem. A [J], 2005, 109(21): 4713—4720 [24]Haddon R. C., Brus L. E., Raghavachari K.. Chem. Phys. Lett.[J], 1986, 125(5/6): 459—464 [25]Nuretdinov I. A., Gubskaya V. P., Yanilkin V. V., Morozov V. I., Zverev V. V., Il′yasov A. V., Fazleeva G. M., Nastapova N. V., Il′matova D. V.. Russ. Chem. Bull.[J], 2001, 50(4): 607—613 [26]Zandler M. E., Smith P. M., Fujitsuka M., Ito O., D′Souza F.. J. Org. Chem.[J], 2002, 67(26): 9122—9129 [27]Herranz M. A., Martin N., Sanchez L., Seoane C., Guldi D. M.. J. Organomet. Chem.[J], 2000, 599(1): 2—7 [28]Fowler P. W., Ceulemans A.. J. Phys. Chem.[J], 1995, 99(2): 508—510 [29]QIAN Ying(钱鹰), HUANG Wei(黄维), LU Zhi-Feng(路志锋), ZHU Xiao-Qin(朱晓勤), MENG Kang(孟康), L Chang-Gui(吕昌贵), CUI Yi-Ping(崔一平). Chem. J. Chinese Universities(高等学校化学学报)[J], 2007, 28(12): 2369—2372 [30]Bhattacharya S., Nayak S. K., Chattopadhyay S., Banerjee M., Mukherjee A. K.. J. Phys. Chem. A [J], 2002, 106(29): 6710—6713 [31]Gu B., Ji W., Patil P. S., Dharmaprakash S. M., Wang H. T.. Appl. Phys. Lett.[J], 2008, 92(9): 091118/1—091118/3 [32]Sutherland R. L., Brant M. C., Heinrichs J., Rogers J. E., Slagle J. E., McLean D. G., Fleitz P. A.. J. Opt. Soc. Am. B [J], 2005, 22(9): 1939—1948 [33]Riggs J.E., Sun Y. P.. J. Phys. Chem. A [J], 1999, 103(4): 485—495 [34]Foley S., Berberan-Santos M. N., Fedorov A., McGarvey D. J., Santos C., Gigante B.. J. Phys. Chem. A [J], 1999, 103(41): 8173—8178 [35]Gao J., Li Q., Zhao H., Li L., Liu C., Gong Q., Qi L.. Chem. Mater.[J], 2008, 20(19): 6263—6269 [36]Ouyang X. H., Zeng H. P., Ji W.. J. Phys. Chem. B[J], 2009, 113(44): 14565—14573 [37]Wei T. H., Huang T. H., Wu T. T., Tsai P. C., Lin M. S.. Chem. Phys. Lett.[J], 2000, 318(1—3): 53—57 [38]Konstantaki M., Kou E. D., Couris S., Janot J. M., Eddaoudi H., Deratani A., Seta P., Leach S.. Chem. Phys. Lett.[J], 2000, 318(4/5): 488—495