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Citation: Fu-ai Teng, Feng-li Liu, Lu Han, Zheng-ju Zhu, Yi-fang Zhang, Zhi-jin Wu, Zhe-wen Han, Wen-bin Zhang, Hui Li. Design, Synthesis, and Optical/Electronic Properties of a Series of Sphere-Rod Shape Amphiphiles Based on the C60-oligofluorene Conjugates[J]. Chinese Journal of Polymer Science, ;2017, 35(4): 503-514. doi: 10.1007/s10118-017-1899-4 shu

Design, Synthesis, and Optical/Electronic Properties of a Series of Sphere-Rod Shape Amphiphiles Based on the C60-oligofluorene Conjugates

  • a.

    School of Materials Science and Engineering, East China University of Science and Technology, Shanghai 200237, China

  • b.

    Key Laboratory of Polymer Chemistry and Physics of Ministry of Education, College of Chemistry and Molecular Engineering, Center for Soft Matter Science and Engineering, Peking University, Beijing 100871, China

  • Corresponding author: Zhe-wen Han, zwhan@ecust.edu.cn Wen-bin Zhang, wenbin@pku.edu.cn Hui Li, lihui@ecust.edu.cn
  • Received Date: 6 September 2016
    Revised Date: 11 October 2016
    Accepted Date: 12 October 2016

    Fund Project: the Natural Science Foundation of Shanghai 10ZR1407600the International Science & Technology Cooperation Program of China 2010DFB70470

  • A series of sphere-rod shape amphiphiles were designed and synthesized by connecting the rod-like oligofluorenes with different lengths (OFn) to the different positions of the spherical[60]fullerene (C60) through a rigid linkage. The conjugates were characterized by 1H-NMR, 13C-NMR, FTIR, EA and MALDI-TOF mass spectrometry. The optical and electronic properties of the conjugates were studied by UV-Vis absorption spectroscopy, fluorescence spectrometry, and cyclic voltammetry. The results from UV-Vis absorption spectroscopy and cyclic voltammetry indicated that the energy profiles of C60 and OFn remained unchanged when different lengths of OFn were attached to C60. The electron affinities of the OFn-C60 conjugates were close to that of C60, while slight electronic interaction was found between the two individual chromophores (C60 and OFn) in their ground states. The fluorescence spectra exhibited a complete fluorescence quenching in the toluene solution, suggesting an effective energy transfer from OFn to C60. It presents a systematic study on the self-assembly, structure-property relationship, and potential technical applications of the conjugates.
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    1. [1]

      Carroll, J.B., Frankamp, B.L., Srivastava, S. and Rotello, V.M., J. Mater. Chem., 2004, 14:690  doi: 10.1039/b311423f

    2. [2]

      Horsch, M.A., Zhang, Z. and Glotzer, S.C., Nano Lett., 2006, 6:2406  doi: 10.1021/nl0614415

    3. [3]

      Iacovella, C.R., Horsch, M.A., Zhang, Z. and Glotzer, S.C., Langmuir, 2005, 21:9488  doi: 10.1021/la051035l

    4. [4]

      Zhang, Z., Horsch, M.A., Lamm, M.H. and Glotze, S.C., Nano Lett., 2003, 3:1341  doi: 10.1021/nl034454g

    5. [5]

      Zhang, X., Chan, E.R. and Glotzer, S.C., J. Chem. Phys., 2005, 123:184718  doi: 10.1063/1.2060664

    6. [6]

      Damasceno, P.F., Engel, M. and Glotzer, S.C., Science, 2012, 337:453  doi: 10.1126/science.1220869

    7. [7]

      Sindoro, M., Yanai, N., Jee, A.Y. and Granick, S., Acc. Chem. Res., 2014, 47:459  doi: 10.1021/ar400151n

    8. [8]

      Rao, C. N. R. , Vivekchand, S. R. C. , Biswas, K. and Govindaraj, A. , Dalton Trans. , 2007, DOI:10.1039/b708342d:3728.

    9. [9]

      Lattuada, M. and Hatton, T.A., Nano Today, 2011, 6:286  doi: 10.1016/j.nantod.2011.04.008

    10. [10]

      Frey, N.A., Peng, S., Cheng, K. and Sun, S.H., Chem. Soc. Rev., 2009, 38:2532  doi: 10.1039/b815548h

    11. [11]

      Glotzer, S.C., Science, 2004, 306:419  doi: 10.1126/science.1099988

    12. [12]

      Glotzer, S.C., Horsch, M.A., Iacovella, C.R., Zhang, Z., Chan, E.R. and Zhang, X., Curr. Opin. Colloid Interface Sci., 2005, 10:287  doi: 10.1016/j.cocis.2005.09.011

    13. [13]

      Li, Y., Dong, X.H., Guo, K., Wang, Z., Chen, Z., Wesdemiotis, C., Quirk, R.P., Zhang, W.B. and Cheng, S.Z.D., ACS Macro Lett., 2012, 1:834  doi: 10.1021/mz300196x

    14. [14]

      Zhang, W.B., Yu, X., Wang, C.L., Sun, H.J., Hsieh, I.F., Li, Y., Dong, X.H., Yue, K., van Horn, R. and Cheng, S.Z.D., Macromolecules, 2014, 47:1221  doi: 10.1021/ma401724p

    15. [15]

      Zhang, W.B. and Cheng, S.Z.D., Chinese J. Polym. Sci., 2015, 33:797  doi: 10.1007/s10118-015-1653-8

    16. [16]

      Bushby, R.J., Hamley, I.W., Liu, Q., Lozmana, O.R. and Lydon, J.E., J. Mater. Chem., 2005, 15:4429  doi: 10.1039/b509492e

    17. [17]

      Kouwer, P.H.J. and Mehl, G.H., J. Mater. Chem., 2009, 19:1564  doi: 10.1039/b819877b

    18. [18]

      Date, R.W. and Bruce, D.W., J. Am. Chem. Soc., 2003, 125:9012  doi: 10.1021/ja0357947

    19. [19]

      Holmberg, K. , Jonsson, B. , Kronberg, B. and Lindman, B. , "Surfactants and polymers in aqueous solution", John Wiley & Sons Ltd, England, 2003

    20. [20]

      Bates, F.S. and Fredrickson, G.H., Phys. Today, 1999, 52:32

    21. [21]

      Percec, V., Wilson, D.A., Leowanawat, P., Wilson, C.J., Hughes, A.D., Kaucher, M.S., Hammer, D.A., Levine, D.H., Kim, A.J., Bates, F.S., Davis, K.P., Lodge, T.P., Klein, M.L., DeVane, R.H., Aqad, E., Rosen, B.M., Argintaru, A.O., Sienkowska, M.J., Rissanen, K., Nummelin, S. and Ropponen, J., Science, 2010, 328:1009  doi: 10.1126/science.1185547

    22. [22]

      Auyeung, E., Li, T.I., Senesi, A.J., Schmucker, A.L., Pals, B.C., de la Cruz, M.O. and Mirkin, C.A., Nature, 2014, 505:73

    23. [23]

      Xiong, H., Sfeir, M.Y. and Gang, O., Nano Lett., 2010, 10:4456  doi: 10.1021/nl102273c

    24. [24]

      Sun, H.J., Tu, Y., Wang, C.L., Horn, R.M.V., Tsai, C.C., Graham, M.J., Sun, B., Lotz, B., Zhang, W.B. and Cheng, S.Z.D., J. Mater. Chem., 2011, 21:14240  doi: 10.1039/c1jm10954e

    25. [25]

      Liang, W.W., Huang, C.F., Wu, K.Y., Wu, S.L., Chang, S.T., Cheng, Y.J. and Wang, C.L., Chem. Sci., 2016, 7:2768  doi: 10.1039/C5SC04242A

    26. [26]

      Zhang, M.Y., Gu, K.H., Zhou, Y., Zhou, S., Fan, X.H. and Shen, Z., Chem. Commun., 2016, 52:3923  doi: 10.1039/C5CC10620F

    27. [27]

      Liu, H., Luo, J., Shan, W., Guo, D., Wang, J., Hsu, C.H., Huang, M., Zhang, W., Lotz, B., Zhang, W.B., Liu, T., Yue, K. and Cheng, S.Z.D., ACS Nano, 2016, 10:6585  doi: 10.1021/acsnano.6b01336

    28. [28]

      Liu, H., Hsu, C.H., Lin, Z., Shan, W., Wang, J., Jiang, J., Huang, M., Lotz, B., Yu, X., Zhang, W.B., Yue, K. and Cheng, S.Z.D., J. Am. Chem. Soc., 2014, 136:10691  doi: 10.1021/ja504497h

    29. [29]

      Ma, S., Hu, Y. and Wang, R., Macromolecules, 2015, 48:3112  doi: 10.1021/ma5026219

    30. [30]

      Yu, X., Yue, K., Hsieh, I.F., Li, Y., Dong, X.H., Liu, C., Xin, Y., Wang, H.F., Shi, A.C., Newkome, G.R., Ho, R.M., Chen, E.Q., Zhang, W.B. and Cheng, S.Z.D., Proc. Natl. Acad. Sci. USA, 2013, 110:10078  doi: 10.1073/pnas.1302606110

    31. [31]

      Langa, F. and Nierengarten, J. F. , "Fullerenes: principles and applications", The Royal Society of Chemistry, Cambridge, 2007

    32. [32]

      Zhang, W.B., Tu, Y., Ranjan, R., van Horn, R.M., Leng, S., Wang, J., Polce, M., Wesdemiotis, C., Quirk, R.P., Newkome, G.R. and Cheng, S.Z.D., Macromolecules, 2008, 41:515  doi: 10.1021/ma702345r

    33. [33]

      Teng, F.A., Cao, Y., Qi, Y.J., Huang, M., Han, Z.W., Cheng, S.Z.D., Zhang, W.B. and Li, H., Chem. Asian J., 2013, 8:1223  doi: 10.1002/asia.201300043

    34. [34]

      Gomez, R. and Segura, J.L., Tetrahedron, 2009, 65:540  doi: 10.1016/j.tet.2008.10.077

    35. [35]

      Lin, Y., Li, Y. and Zhan, X., Chem. Soc. Rev., 2012, 41:4245  doi: 10.1039/c2cs15313k

    36. [36]

      Nierengarten, J.F., Sol. Energy Mater. Sol. Cells, 2004, 83:187  doi: 10.1016/j.solmat.2004.02.024

    37. [37]

      Figueira-Duarte, T.M., Gegout, A. and Nierengarten, J.F., Chem. Commun., 2007, 109

    38. [38]

      Segura, J.L., Martín, N. and Guldi, D.M., Chem. Soc. Rev., 2005, 34:31  doi: 10.1039/B402417F

    39. [39]

      Kumar, K.S. and Patnaik, A., Langmuir, 2011, 27:11017  doi: 10.1021/la201849u

    40. [40]

      Liu, L., Wong, W.Y., Lam, Y.W. and Tam, W.Y., Inorg. Chim. Acta, 2007, 360:109  doi: 10.1016/j.ica.2006.07.037

    41. [41]

      Li, Z.H., Wong, M.S., Tao, Y. and Lu, J., Chem. Eur. J., 2005, 11:3285  doi: 10.1002/(ISSN)1521-3765

    42. [42]

      Katsis, D., Geng, Y.H., Ou, J.J., Culligan, S.W., Trajkovska, A., Chen, S.H. and Rothberg, L.J., Chem. Mater., 2002, 14:1332  doi: 10.1021/cm010679l

    43. [43]

      Dudek, S.P., Pouderoijen, M., Abbel, R., Schenning, A.P.H.J. and Meijer, E.W., J. Am. Chem. Soc., 2005, 127:11763  doi: 10.1021/ja052054k

    44. [44]

      Hummelen, J.C., Knight, B.W., Lepeq, F., Wudl, F., Yao, J. and Wilkins, C.L., J. Org. Chem., 1995, 60:532  doi: 10.1021/jo00108a012

    45. [45]

      Sijbesma, R., Srdanov, G., Wudl, F., Castoro, J.A., Wilkins, C., Friedman, S.H., DeCamp, D.L. and Kenyon, G.L., J. Am. Chem. Soc., 1993, 115:6510  doi: 10.1021/ja00068a006

    46. [46]

      An, Y.Z., Rubin, Y., Schaller, C. and McElvany, S.W., J. Org. Chem., 1994, 59:2927  doi: 10.1021/jo00090a006

    47. [47]

      Kay, K.Y., Kim, L.H. and Oh, I.C., Tetrahedron Lett., 2000, 41:1397  doi: 10.1016/S0040-4039(99)02301-1

    48. [48]

      Kay, K.Y. and Oh, I.C., Tetrahedron Lett., 1999, 40:1709  doi: 10.1016/S0040-4039(99)00033-7

    49. [49]

      Chi, C., Im, C., Enkelmann, V., Ziegler, A., Lieser, G. and Wegner, G., Chem. Eur. J., 2005, 11:6833  doi: 10.1002/(ISSN)1521-3765

    50. [50]

      Zhou, X.H., Zhang, Y., Xie, Y.Q., Cao, Y. and Pei, J., Macromolecules, 2006, 39:3830  doi: 10.1021/ma0601262

    51. [51]

      Guldi, D.M., Luo, C., Swartz, A., Gomez, R., Segura, J.L. and Martin, N., J. Phys. Chem. A, 2004, 108:455  doi: 10.1021/jp034186a

    52. [52]

      Guldi, D.M., Luo, C., Swartz, A., Gomez, R., Segura, J.L., Martin, N., Brabec, C. and Sariciftci, N.S., J. Org. Chem., 2002, 67:1141  doi: 10.1021/jo0108313

    53. [53]

      Gegout, A., Nierengarten, J.F., Delavaux-Nicot, B., Duhayon, C., Saquet, A., Listorti, A., Belbakra, A., Chiorboli, C. and Armaroli, N., Chem. Eur. J., 2009, 15:8825  doi: 10.1002/chem.v15:35

    54. [54]

      Zhang, Y., Xu, Z., Cai, L., Lai, G., Qiu, H. and Shen, Y., J. Photochem. Photobiol. A, 2008, 200:334  doi: 10.1016/j.jphotochem.2008.08.011

    55. [55]

      Eckert, J.F., Nicoud, J.F., Nierengarten, J.F., Liu, S.G., Echegoyen, L., Barigelletti, F., Armaroli, N., Ouali, L., Krasnikov, V. and Hadziioannou, G., J. Am. Chem. Soc., 2000, 122:7467  doi: 10.1021/ja9941072

    56. [56]

      Peeters, E., Hal, P.A.V., Knol, J., Brabec, C.J., Sariciftci, N.S., Hummelen, J.C. and Janssen, R.A.J., J. Phys. Chem. B, 2000, 104:10174  doi: 10.1021/jp001717b

    57. [57]

      Misek, J., Jentzsch, A.V., Sakurai, S.I., Emery, D., Mareda, J. and Matile, S., Angew. Chem. Int. Ed., 2010, 49:7680  doi: 10.1002/anie.v49:42

    58. [58]

      Knight, B., Martín, N., Ohno, T., Ortí, E., Rovira, C., Veciana, J., Vidal-Gancedo, J., Viruela, P., Viruela, R. and Wudl, F., J. Am. Chem. Soc., 1997, 119:9871  doi: 10.1021/ja962299k

    59. [59]

      Molina-Ontoria, A., Fernández, G., Wielopolski, M., Atienza, C., Sánchez, L., Gouloumis, A., Clark, T., Martín, N. and Guldi, D.M., J. Am. Chem. Soc., 2009, 131:12218  doi: 10.1021/ja9024269

    60. [60]

      Wudl, F., Sukuki, T. and Prato, M., Synth. Met., 1993, 59:297  doi: 10.1016/0379-6779(93)91163-V

    61. [61]

      Eiermann, M., Haddon, R.C., Knight, B., Li, Q.C., Maggine, M., Martín, N., Ohno, T., Prato, M., Suzuki, T. and Wudl, F., Angew. Chem. Int. Ed., 1995, 34:1591  doi: 10.1002/(ISSN)1521-3773

    62. [62]

      Illescas, B.M. and Martín, N., C. R. Chimie, 2006, 9:1038  doi: 10.1016/j.crci.2005.11.016

    63. [63]

      Gong, X., Tong, M., Brunetti, F.G., Seo, J., Sun, Y., Moses, D., Wudl, F. and Heeger, A.J., Adv. Mater., 2011, 23:2272  doi: 10.1002/adma.201003768

    64. [64]

      Dennler, G., Scharber, M.C. and Brabec, C.J., Adv. Mater., 2009, 21:1323  doi: 10.1002/adma.v21:13

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