Citation: Ruo-lin Wang, Rui Qu, Yan Zhai, Chen Jing, Ang Li, Ying-li An, Lin-qi Shi. Enhanced Electron Transfer Ability via Coordination in Block Copolymer/Porphyrin/Fullerene Micelle[J]. Chinese Journal of Polymer Science, ;2017, 35(11): 1328-1341. doi: 10.1007/s10118-017-1973-y shu

Enhanced Electron Transfer Ability via Coordination in Block Copolymer/Porphyrin/Fullerene Micelle

State Key Laboratory of Medicinal Chemical Biology, Key Laboratory of Functional Polymer Materials, Ministry of Education, Collaborative Innovation Center of Chemical Science and Engineering(Tianjin), Institute of Polymer Chemistry, Nankai University, Tianjin 300071, China

Corresponding author: Lin-qi Shi, shilinqi@nankai.edu.cn
Received Date: 14 April 2017
Revised Date: 2 May 2017
Accepted Date: 8 May 2017

Fund Project: the National Natural Science Foundation of China 51503104the National Natural Science Foundation of China 91527306the Natural Science Foundation of Tianjin 16JCQNJC03000the National Natural Science Foundation of China 21620102005the National Natural Science Foundation of China 51390483the Natural Science Foundation of Tianjin 16JCQNJC02500the National Natural Science Foundation of China 51603231

Inspired by structures of antenna-reaction centers in photosynthesis, the complex micelle was prepared from zinc tetra-phenyl porphyrin (ZnTPP), fullerene derivative (PyC₆₀) and poly(ethylene glycol)-block-poly(ε-caprolactone) (PEG-b-PCL). The core-shell structure made the hydrophobic donor-acceptor system work in aqueous. In micellar core, coordination interaction occurred between ZnTPP and PyC₆₀ molecules which ensured the enhanced energy migration from the donor to the acceptor. The enhanced interaction between porphyrin and fullerene was confirmed by absorption, steady-state fluorescence and transient fluorescence. The generation of singlet oxygen and superoxide radical was detected by iodide method and reduction of nitro blue tetrazolium, respectively, which confirmed that electron transfer reaction in the complex micellar core occurred. Moreover, the complex micelle exhibited effective electron transfer performance in photodebromination of 2, 3-dibromo-3-phenylpropionic acid. The complex micellar structure endowed the donor-acceptor system with improved stability under irradiation. This strategy could be helpful for designing new electron transfer platform and artificial photosynthetic system.
- Porphyrin,
- Fullerene,
- Micelle,
- Coordination,
- Electron transfer
1. [1]
  Rabinowitch, E. and Govindjee, "Photosynthesis", Wiley, New York, 1969
2. [2]
  D'Souza, F., Coord. Chem. Rev., 2016, 322:104 doi: 10.1016/j.ccr.2016.05.012
3. [3]
  Izumi, Y., Coord. Chem. Rev., 2013, 257(1):171 doi: 10.1016/j.ccr.2012.04.018
4. [4]
  Bottari, G., Trukhina, O., Ince, M. and Torres, T., Coord. Chem. Rev., 2012, 256(21):2453
5. [5]
  Croce, R. and van Amerongen, H., Nat. Chem. Biol., 2014, 10(7):492 doi: 10.1038/nchembio.1555
6. [6]
  Chai, Z., Ma, R., Zhang, Z. and Shi, L., Acta Polymerica Sinica (in Chinese), 2012, (10):1108
7. [7]
  Kadish, K. M. , Smith, K. M. and Guilard, R. , "The porphyrin handbook: inorganic, organometallic and coordination chemistry", Elsevier, 2000, p. 3
8. [8]
  Hiroto, S., Miyake, Y. and Shinokubo, H., Chem. Rev., 2017, 117:2910 doi: 10.1021/acs.chemrev.6b00427
9. [9]
  Kroto, H.W., Heath, J.R., O'Brien, S.C., Curl, R.F. and Smalley, R.E., Nature, 1985, 318(6042):162 doi: 10.1038/318162a0
10. [10]
  Thilgen, C. and Diederich, F., Chem. Rev., 2006, 106(12):5049 doi: 10.1021/cr0505371
11. [11]
  Vizuete, M., Barrejón, M., Gómez-Escalonilla, M.J. and Langa, F., Nanoscale, 2012, 4(15):4370 doi: 10.1039/c2nr30376k
12. [12]
  Xie, Q., Perez-Cordero, E. and Echegoyen, L., J. Am. Chem. Soc., 1992, 114(10):3978 doi: 10.1021/ja00036a056
13. [13]
  Wróbel, D. and Graja, A., Coord. Chem. Rev., 2011, 255(21):2555
14. [14]
  Chai, Z., Li, A., An, Y. and Shi, L., Acta Polymerica Sinica (in Chinese), 2017, (2):393
15. [15]
  Zhang, J.W., Li, H.Y., Fan, H., Zhang, Y., Jiang, L., Wang, C.R., Ma, C. and Liu, Y.J., Chinese J. Polym. Sci., 2014, 32(10):1357 doi: 10.1007/s10118-014-1525-7
16. [16]
  Sánchez, L., Sierra, M., Martín, N., Myles, A.J., Dale, T.J., Rebek, J., Seitz. W. and Guldi, D.M., Angew. Chem., 2006, 118(28):4753 doi: 10.1002/(ISSN)1521-3757
17. [17]
  D'Souza, F. and Ito, O., Chem. Commun., 2009, (33):4913 doi: 10.1039/b905753f
18. [18]
  D'Souza, F., Venukadasula, G.M., Yamanaka, K.I., Subbaiyan, N.K., Zandler, M.E. and Ito, O., Org. Biomol. Chem., 2009, 7(6):1076 doi: 10.1039/b822362a
19. [19]
  Williams, D.E., Dolgopolova, E.A., Godfrey, D.C., Ermolaeva, E.D., Pellechia, P.J., Greytak, A.B., Smith, M.D., Avdoshenko, S.M., Popov, A.A. and Shustova, N.B., Angew. Chem. Int. Ed., 2016, 55(31):9070 doi: 10.1002/anie.201603584
20. [20]
  D'Souza, F., Gadde, S., Zandler, M.E., Arkady, K., El-Khouly, M.E., Fujitsuka, M. and Ito, O., J. Phys. Chem. A, 2002, 106(51):12393 doi: 10.1021/jp021926r
21. [21]
  Lim, G.N., Maligaspe, E., Zandler, M.E. and D'Souza, F., Chem. Eur. J., 2014, 20(51):17089 doi: 10.1002/chem.201404671
22. [22]
  D'Souza, F., Deviprasad, G.R., Zandler, M.E., Hoang, V.T., Klykov, A., van Stipdonk, M., Perera, A., El-Khouly, M.E., Fujitsuka, M. and Ito, O., J. Phys. Chem. A, 2002, 106(13):3243 doi: 10.1021/jp013165i
23. [23]
  Boyd, P.D. and Reed, C.A., Acc. Chem. Res., 2005, 38(4):235 doi: 10.1021/ar040168f
24. [24]
  Hasobe, T., Imahori, H., Kamat, P.V., Ahn, T.K., Kim, S.K., Kim, D., Fujimoto, A., Hirakawa, T. and Fukuzumi, S., J. Am. Chem. Soc., 2005, 127(4):1216 doi: 10.1021/ja047768u
25. [25]
  Kubo, Y., Sugasaki, A., Ikeda, M., Sugiyasu, K., Sonoda, K., Ikeda, A., Takeuchi, M. and Shinkai, S., Org. Lett., 2002, 4(6):925 doi: 10.1021/ol017299q
26. [26]
  D'Souza, F., Chitta, R., Gadde, S., Zandler, M.E., McCarty, A.L., Sandanayaka, A.S., Araki, Y. and Ito, O., Chem. Eur. J., 2005, 11(15):4416 doi: 10.1002/chem.v11:15
27. [27]
  Costa, J.I., Farinha, A.S., Neves, M.G. and Tomé, A.C., Dyes Pigm., 2016, 135:163 doi: 10.1016/j.dyepig.2016.02.035
28. [28]
  D'Souza, F., Chitta, R., Gadde, S., Zandler, M.E., Sandanayaka, A.S., Araki, Y. and Ito, O., Chem. Commun., 2005, (10):1279 doi: 10.1039/B416736H
29. [29]
  Calderon, R.M.K., Valero, J., Grimm, B., de Mendoza, J. and Guldi, D.M., J. Am. Chem. Soc., 2014, 136(32):11436 doi: 10.1021/ja5052236
30. [30]
  Balbinot, D., Atalick, S., Guldi, D.M., Hatzimarinaki, M., Hirsch, A. and Jux, N., J. Phys. Chem. B, 2003, 107(48):13273 doi: 10.1021/jp0304780
31. [31]
  Wang, N., Zhang, X., Zheng, W., Ouyang, D. and Yang, R., Supramol. Chem., 2015, 27(1-2):72 doi: 10.1080/10610278.2014.909043
32. [32]
  Ruban, A.V., Johnson, M.P. and Duffy, C.D., Energy Environ. Sci., 2011, 4:1643 doi: 10.1039/c0ee00578a
33. [33]
  Wang, R., Qu, R., Jing, C., Zhai, Y., An, Y. and Shi, L., RSC Adv., 2017, 7(17):10100 doi: 10.1039/C7RA00196G
34. [34]
  Fan, J., Wang, Y., Blake, A.J., Wilson, C., Davies, E.S., Khlobystov, A.N. and Schröder, M., Angew. Chem. Int. Ed., 2007, 46(42):8013 doi: 10.1002/(ISSN)1521-3773
35. [35]
  El-Khouly, M.E., Gadde, S., Deviprasad, G.R., Fujitsuka, M., Ito, O. and D'Souza, F., J Porphyr. Phthalocya., 2003, 7(1):1 doi: 10.1142/S1088424603000021
36. [36]
  Scatchard, G., Ann. New York Acad. Sci., 1949, 51:660 doi: 10.1111/nyas.1949.51.issue-4
37. [37]
  Leznoff, C. C. and Lever, A. B. P. , "Phthalocyanines: properties and applications", VCH, New York, 1989, p. 133
38. [38]
  Abdel-Razik, H.H., Asghar, B.H. and Kenawy, E., Chinese J. Polym. Sci., 2013, 31(2):242 doi: 10.1007/s10118-013-1184-0
39. [39]
  Ohkubo, K., Karr, P.A., Fukuzumi, S. and D'Souza, F., Chem. Commun., 2013, 49(69):7614 doi: 10.1039/c3cc43510e
40. [40]
  Yamakoshi, Y., Umezawa, N., Ryu, A., Arakane, K., Miyata, N., Goda, Y., Masumizu, T. and Nagano, T., J. Am. Chem. Soc., 2003, 125(42):12803 doi: 10.1021/ja0355574
41. [41]
  Slavětínská, L., Mosinger, J. and Kubát, P., J. Photochem. Photobiol., A, 2008, 195(1):1 doi: 10.1016/j.jphotochem.2007.09.007
42. [42]
  Ballatore, M.B., Durantini, J., Gsponer, N.S., Suarez, M.B., Gervaldo, M., Otero, L., Spesia, M. and Durantini, E.N., Environ. Sci. Technol., 2015, 49(12):7456 doi: 10.1021/acs.est.5b01407
43. [43]
  Takagi, K., Miyake, N., Nakamura, E., Usami, H., Sawaki, Y. and Iwamura, H., J. Chem. Soc., Faraday Trans. 1, 1988, 84(10):3475 doi: 10.1039/f19888403475
44. [44]
  Horváth, O., Huszánk, R., Valicsek, Z. and Lendvay, G., Coord. Chem. Rev., 2000, 78:2597
45. [45]
  Chai, Z., Gao, H., Ren, J., An, Y. and Shi, L., RSC Adv., 2013, 3(40):18351 doi: 10.1039/c3ra42616e
46. [46]
  Wang, X., Chai, Z., Ma, R., Zhao, L., Zhang, Z., An, Y. and Shi, L., J. Colloid Interface Sci., 2012, 388(1):80 doi: 10.1016/j.jcis.2012.08.045
47. [47]
  Ichiki, T., Matsuo, Y., and Nakamura, E., Chem. Commun., 2013, 49(3):279 doi: 10.1039/C2CC36988E
48. [48]
  Huszánk, R., Lendvay, G. and Horváth, O., JBIC, J. Biol. Inorg. Chem., 2007, 12(5):681 doi: 10.1007/s00775-007-0217-y
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