Citation: Wu Jie, Zhang Xiuli, Zhang Lijun, Wei Yun, Zhou Shuangliu. Synthesis and Catalytic Activity of Dinuclear Rare-Earth Metal Complexes with Nitrogen-Containing Bridged Dipyrrolyl Ligand towards Ring-Opening Polymerization of e-Caprolactone[J]. Chinese Journal of Organic Chemistry, ;2020, 40(3): 801-805. doi: 10.6023/cjoc201908010 shu

Synthesis and Catalytic Activity of Dinuclear Rare-Earth Metal Complexes with Nitrogen-Containing Bridged Dipyrrolyl Ligand towards Ring-Opening Polymerization of e-Caprolactone

  • Corresponding author: Zhang Lijun, zljun@ahnu.edu.cn Zhou Shuangliu, slzhou@ahnu.edu.cn
  • Received Date: 6 August 2019
    Revised Date: 13 October 2019
    Available Online: 9 November 2019

    Fund Project: Project supported by the National Natural Science Foundation of China Nos. 21672004Project supported by the National Natural Science Foundation of China 21602004Project supported by the National Natural Science Foundation of China (Nos. 21672004, 21602004)

Figures(3)

  • Reaction of RE(CH2SiMe3)3(THF)2 with 1.5 equiv. of (C4H3NHCH2)2NCH3 (1) in toluene gave nitrogen-containing bridged dipyrrolyl dinuclear rare-earth metal complexes[η1:η1:η1-(C4H3NCH2)2NCH3]RE{m-η5:η1:η5:η1:η1-(C4H3NCH2)2N-CH3}RE[η1:η1:η1-(C4H3NCH2)2NCH3](THF)[RE=Y (2), Er (3), Yb (4)]. All complexes were fully characterized by spectroscopic methods and elemental analyses. The structures of complexes 2 and 4 were further determined by single-crystal X-ray diffraction. The catalytic properties of rare-earth metal complexes on the ring-opening polymerization of e-caprolactone have been studied.
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    1. [1]

      (a) Müller H. M., Seebach D.Angew. Chem., Int. Ed., 1993, 32: 477.
      (b) Ni Q., Yu L.J. Am. Chem. Soc., 1998, 120: 1645.
      (c) Okada M.Prog. Polym. Sci., 2002, 27: 87.
      (d) Wiegand T., Karr J., Steinkruger J. D., Hiebner K., Simetich B., Beatty M., Redepenning J.Chem. Mater., 2008, 20: 5016.

    2. [2]

      For reviews, see: (a) Shen Q., Yao Y.Chin. J. Org. Chem., 2001, 21: 1018(in Chinese).
      (沈琪, 姚英明, 有机化学,, 2001, 21: 1018.)
      (b) Dechy-Cabaret O., Martin-Vaca B., Bourissou D.Chem. Rev., 2004, 104: 6147
      (c) Wu J. C., Yu T.-L., Chen C.-T., Lin C.-C.Coord. Chem. Rev., 2006, 250: 602.
      (d) Sutar A. K., Maharana T., Dutta S., Chen C.-T., Lin C.-C.Chem. Soc. Rev., 2010, 39: 1724.
      (e) Wei Y., Wang S., Zhou S.Dalton Trans., 2016, 45: 4471.
      (f) Zhao N.Chin. J. Org. Chem., 2017, 37: 1139(in Chinese).
      (赵宁, 有机化学,, 2017, 37: 1139.)

    3. [3]

      (a) Wang, Z; Qi C.Organometallics, 2007, 26: 2243.
      (b) Ko B.-T., Lin C.-C.J. Am. Chem. Soc., 2001, 123: 7973.
      (c) Hsueh M.-L., Huang B.-H., Wu J., Lin C.-C.Macromolecules, 2005, 38: 9482.
      (d) Bhunia M., Vijaykumar G., Adhikari D., Mandal S. K.Inorg. Chem., 2017, 56: 14459.

    4. [4]

      (a) Shueh M.-L., Wang Y.-S., Huang B.-H., Kuo C.-Y., Lin C.-C.Macromolecules, 2004, 37: 5155.
      (b) Sarazin Y., Schormann M., Bochmann M.Organometallics, 2004, 23: 3296.
      (c) Chisholm M. H., Gallucci J. C., Phomphrai K.Inorg. Chem., 2004, 43: 6717.
      (d) Xu X., Chen Y., Zou G., Ma Z., Li G.J. Organomet. Chem., 2010, 695: 1155.
      (e) Huang Y., Wang W., Lin C.-C., Blake M. P., Clark L., Schwarzb A. D., Mountford P.Dalton Trans., 2013, 42: 9313.
      (f) Huang Y., Kou X., Duan Y., Ding F., Yin Y., Wang W., Yang Y.Dalton Trans., 2018, 47: 8121.

    5. [5]

      (a) Duda A., Penczek S.Macromolecules, 1995, 28: 5981.
      (b) Ovitt, T M., Coates G. W.J. Am. Chem. Soc., 1999, 121: 4072.
      (c) Radano C. P., Baker G. L., Smith M. R.J. Am. Chem. Soc., 2000, 122: 1552.
      (d) Liu Y.-C., Ko B.-T., Lin C.-C.Macromolecules, 2001, 34: 6196.
      (e) Gao A., Mu Y., Zhang J., Yao W.Eur. J. Inorg. Chem., 2009, 3613.
      (f) Zhang W., Wang Y., Cao J., Wang L., Pan Y., Redshaw C., Sun W.-H.Organometallics, 2011, 30: 6253.
      (g) Li W., Yao Y., Zhang Y., Shen Q.Chin. J. Chem., 2012, 30: 609.
      (h) Chen L., Li W.Yuan D., Zhang Y., Shen Q., Yao Y.Inorg. Chem., 2015, 54: 4699.
      (i) Hao P.; Yang Z., Li W., Ma X., Roesky H. W., Yang Y., Li J.Organometallics, 2015, 34: 105.
      (j) Wei Y., Wang S., Zhu X., Zhou S., Mu X., Huang Z., Hong D.Organometallics, 2016, 35: 2621.
      (k) Lee C.-L., Lin Y.-F., Jiang M.-T., Lu W.-Y., Vandavasi J. K., Wang L.-F., Lai Y.-C., Chiang M. Y., Chen H.-Y.Organometallics, 2017, 36: 1936.

    6. [6]

      (a) Hannant M. D., Schormann M., Bochmann M.Dalton Trans., 2002, 4071.
      (b) Williams C. K., Breyfogle L. E., Choi S. K., Nam W., Young V. G., Hillmyer M. A., Tolman W. B.J. Am. Chem. Soc., 2003, 125: 11350.
      (c) Chakraborty D., Chen E. Y.-X.Organometallics, 2003, 22: 769.
      (d) Chen H.-Y., Huang B.-H., Lin C.-C.Macromolecules, 2005, 38: 5400.
      (e) Chai Z.-Y., Zhang C., Wang Z.-X.Organometallics, 2008, 27: 1626.
      (f) Zhou S., Jiang Y., Xie T., Wu Z., Zhou L., Xu W., Zhang L., Wang S.Chin. J. Chem., 2012, 30: 2176.
      (g) Ma W.-A.; Wang Z.-X.Organometallics, 2011, 30: 4364.

    7. [7]

      (a) Deshayes G., Mercier F. A. G., Degée P., Verbruggen I. I., Biesemans M., Willem R., Dubois P.Chem. Eur. J., 2003, 9: 4346.
      (b) Bratton D., Brown M., Howdle S. M.Macromolecules, 2005, 38: 1190.
      (c) Dove A. P., Gibson V. C., Marshall E. L., Rzepa H. S., White A. J. P., Williams D. J.J. Am. Chem. Soc., 2006, 128: 9834.
      (d) Chagneux N., Trimaille T., Rollet M., Beaudoin E., Gérard P., Bertin D., Gigmes D.Macromolecules, 2009, 42: 9435.

    8. [8]

      (a) Thomas D., Arndt P., Peulecke N., Spannenberg A., Kempe R., Rosenthal U.Eur. J. Inorg. Chem., 1998, 1351.
      (b) Takeuchi D., Nakamura T., Aida T.Macromolecules, 2000, 33: 725.
      (c) Gowda R. R., Chakraborty D., Ramkumar V.Eur. J. Inorg. Chem., 2009, 2981.
      (d) Zhou F., Lin M., Li L., Zhang X., Chen Z., Li Y., Zhao Y., Wu J., Qian G., Hu B., Li W.Organometallics, 2011, 30: 1283.
      (e) Duan Y., Hu Z., Yang B., Ding F., Wang W., Huang Y., Yang Y.Dalton Trans., 2017, 46: 11259

    9. [9]

      (a) Evans W. J., Katsumata H.Macromolecules, 1994, 27: 2330.
      (b) Nishiura M., Hou Z., Koizumi T., Imamoto T., Wakatsuki Y.Macromolecules, 1999, 32: 8245.
      (c) Kerton F. M., Whitwood A. C., Willans C. E.Dalton Trans., 2004, 2237.
      (d) Sun H., Li H., Yao C., Yao Y., Sheng H., Shen Q.Chin. J. Chem., 2005, 23: 1541
      (e) Huang J., Yu J., Wu G., Sun W., Shen Z.Chin. Chem. Lett., 2009, 20: 1357.
      (f) Clark L., Deacon G. B., Forsyth C. M., Junk P. C., Mountford P., Townley J. P.Dalton Trans., 2010, 39: 6693.
      (g) Wang L., Liang Z., Ni X., Shen Z.Chin. Chem. Lett., 2011, 22: 249.
      (h) Susperregui N., Kramer M. U., Okuda J., Maron L.Organometallics, 2011, 30: 1326.
      (i) Gu Z., Li L., Bao Q., Yuan F.Chin. J. Chem., 2015, 33: 563.

    10. [10]

      (a) Stevels W. M., Ankone M. J. K., Dijkstra P. J., Feijen J.Macromolecules, 1996, 29: 8296.
      (b) Zhang L.-F., Shen Z.-Q., Yu C.-P.Chin. J. Chem., 2003, 21: 1236.
      (c) Wang J., Yao Y., Zhang Y., Shen Q.Inorg. Chem., 2009, 48: 744.
      (d) Wang X., Brosmer J. L., Thevenon A., Diaconescu P. L.Organometallics, 2015, 34: 4700.

    11. [11]

      (a) Zhou S., Wang S., Yang G., Li Q., Zhang L., Yao Z., Zhou Z., Song H.Organometallics, 2007, 26: 3755.
      (b) Yang Y., Li S., Cui D., Chen X., Jing X.Organometallics, 2007, 26, 671.
      (c) Zhang L., Wang Y., Shen L., Zhang T.Chin. J. Chem., 2010, 28: 1019.
      (d) Zhou S., Wu S., Zhu H., Wang S., Zhu X., Zhang L., Yang G., Cui D., Wang H.Dalton Trans., 2011, 40: 9447.

    12. [12]

      (a) Gao W., Cui D., Liu X., Zhang Y., Mu Y.Organometallics, 2008, 27: 5889.
      (b) Yang J., Xu P., Luo Y.Chin. J. Chem., 2010, 28: 457.

    13. [13]

      (a) Iftner C., Bonnet F., Nief F., Visseaux M., Maron L.Organometallics, 2011, 30: 4482.
      (b) Schmid M., Guillaume S. M., Roesky P. W.Organometallics, 2014, 33: 5392.

    14. [14]

      (a) Luo Y., Yao Y., Shen Q., Sun J., Weng L.J. Organomet. Chem., 2002, 662: 144.
      (b) Villiers C., Thuery P., Ephritikhine M. A.Eur. J. Inorg. Chem., 2004, 4624.

    15. [15]

      Stanlake L. J. E., Beard J. D., Schafer L. L.Inorg. Chem., 2008, 47:8062.  doi: 10.1021/ic8010635

    16. [16]

      Zhou S., Yin C., Wang H., Zhu X., Yang G., Wang S.Inorg. Chem. Commun., 2011, 14:1196.  doi: 10.1016/j.inoche.2011.04.015

    17. [17]

      Li Y., Shi Y., Odom A. L.J. Am. Chem. Soc., 2004, 126:1794-.  doi: 10.1021/ja038320g

    18. [18]

      Estler F., Eickerling G., Herdtweck E., Anwander R.Organometallics, 2003, 22:1212.  doi: 10.1021/om020783s

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