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

Laboratory of Functionalized Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials, College of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241000

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.
- rare-earth metal,
- complex,
- e-caprolactone,
- ring-opening polymerization
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
1. [1]
  Lulu DONG , Jie LIU , Hua YANG , Yupei FU , Hongli LIU , Xiaoli CHEN , Huali CUI , Lin LIU , Jijiang WANG . Synthesis, crystal structure, and fluorescence properties of Cd-based complex with pcu topology. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 809-820. doi: 10.11862/CJIC.20240171
2. [2]
  Anqiu LIU , Long LIN , Dezhi ZHANG , Junyu LEI , Kefeng WANG , Wei ZHANG , Junpeng ZHUANG , Haijun HAO . Synthesis, structures, and catalytic activity of aluminum and zinc complexes chelated by 2-((2,6-dimethylphenyl)amino)ethanolate. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 791-798. doi: 10.11862/CJIC.20230424
3. [3]
  Kaimin WANG , Xiong GU , Na DENG , Hongmei YU , Yanqin YE , Yulu MA . Synthesis, structure, fluorescence properties, and Hirshfeld surface analysis of three Zn(Ⅱ)/Cu(Ⅱ) complexes based on 5-(dimethylamino) isophthalic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1397-1408. doi: 10.11862/CJIC.20240009
4. [4]
  Hongdao LI , Shengjian ZHANG , Hongmei DONG . Magnetic relaxation and luminescent behavior in nitronyl nitroxide-based annuluses of rare-earth ions. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 972-978. doi: 10.11862/CJIC.20230411
5. [5]
  Yue Sun , Liming Yang , Yaohang Cheng , Guanghui An , Guangming Li . Pd(I)-catalyzed ring-opening arylation of cyclopropyl-α-aminoamides: Access to α-ketoamide peptidomimetics. Chinese Chemical Letters, 2024, 35(6): 109250-. doi: 10.1016/j.cclet.2023.109250
6. [6]
  Rong-Nan Yi , Wei-Min He . Visible light/copper catalysis enabled radial type ring-opening of sulfonium salts. Chinese Chemical Letters, 2025, 36(4): 110787-. doi: 10.1016/j.cclet.2024.110787
7. [7]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
8. [8]
  Haodong Wang , Xiaoxu Lai , Chi Chen , Pei Shi , Houzhao Wan , Hao Wang , Xingguang Chen , Dan Sun . Novel 2D bifunctional layered rare-earth hydroxides@GO catalyst as a functional interlayer for improved liquid-solid conversion of polysulfides in lithium-sulfur batteries. Chinese Chemical Letters, 2024, 35(5): 108473-. doi: 10.1016/j.cclet.2023.108473
9. [9]
  Xiang Li , Beibei Zhang , Zhixiang Wang , Xiangyu Chen . Organocatalyzed iodine-mediated reversible-deactivation radical polymerization via photoinduced charge transfer complex catalysis. Chinese Chemical Letters, 2025, 36(6): 110383-. doi: 10.1016/j.cclet.2024.110383
10. [10]
  Qinghong Zhang , Qiao Zhao , Xiaodi Wu , Li Wang , Kairui Shen , Yuchen Hua , Cheng Gao , Yu Zhang , Mei Peng , Kai Zhao . Visible-light-induced ring-opening cross-coupling of cycloalcohols with vinylazaarenes and enones via β-C-C scission enabled by proton-coupled electron transfer. Chinese Chemical Letters, 2025, 36(2): 110167-. doi: 10.1016/j.cclet.2024.110167
11. [11]
  Xue-Jiao Wang , Jun-Li Xin , Hong Xiang , Ze-Yu Zhao , Yu-Hang He , Haibo Wang , Guangyao Mei , Yi-Cheng Mao , Juan Xiong , Jin-Feng Hu . Holotrichones A and B, potent anti-leukemic lindenane-type sesquiterpene trimers with unprecedented complex carbon skeletons from a rare Chloranthus species. Chinese Chemical Letters, 2024, 35(12): 109682-. doi: 10.1016/j.cclet.2024.109682
12. [12]
  Xue Zhao , Mengshan Chen , Dan Wang , Haoran Zhang , Guangzhi Hu , Yingtang Zhou . Ultrafine nano-copper derived from dopamine polymerization & synchronous adsorption achieve electrochemical purification of nitrate to ammonia in complex water environments. Chinese Chemical Letters, 2024, 35(8): 109327-. doi: 10.1016/j.cclet.2023.109327
13. [13]
  Wenjuan Jin , Zelong Chen , Yi Wang , Jiaxuan Li , Jiahui Li , Yuxin Pei , Zhichao Pei . Nano metal-photosensitizer based on Aza-BODIPY-Cu complex for CDT-enhanced dual phototherapy. Chinese Chemical Letters, 2024, 35(7): 109328-. doi: 10.1016/j.cclet.2023.109328
14. [14]
  Guoju Guo , Xufeng Li , Jie Ma , Yongjia Shi , Jian Lv , Daoshan Yang . Photocatalyst/metal-free sequential C–N/C–S bond formation: Synthesis of S-arylisothioureas via photoinduced EDA complex activation. Chinese Chemical Letters, 2024, 35(11): 110024-. doi: 10.1016/j.cclet.2024.110024
15. [15]
  Panpan Wang , Hongbao Fang , Mengmeng Wang , Guandong Zhang , Na Xu , Yan Su , Hongke Liu , Zhi Su . A mitochondria targeting Ir(III) complex triggers ferroptosis and autophagy for cancer therapy: A case of aggregation enhanced PDT strategy for metal complexes. Chinese Chemical Letters, 2025, 36(1): 110099-. doi: 10.1016/j.cclet.2024.110099
16. [16]
  Yanrui Liu , Paramaguru Ganesan , Peng Gao . Harnessing d-f transition rare earth complexes for single layer white organic light emitting diodes. Chinese Journal of Structural Chemistry, 2024, 43(9): 100369-100369. doi: 10.1016/j.cjsc.2024.100369
17. [17]
  Chao Ma , Cong Lin , Jian Li . MicroED as a powerful technique for the structure determination of complex porous materials. Chinese Journal of Structural Chemistry, 2024, 43(3): 100209-100209. doi: 10.1016/j.cjsc.2023.100209
18. [18]
  Mengjuan Sun , Muye Zhou , Yifang Xiao , Hailei Tang , Jinhua Chen , Ruitao Zhang , Chunjiayu Li , Qi Ya , Qian Chen , Jiasheng Tu , Qiyue Wang , Chunmeng Sun . Reversibly size-switchable polyion complex micelles for antiangiogenic cancer therapy. Chinese Chemical Letters, 2024, 35(7): 109110-. doi: 10.1016/j.cclet.2023.109110
19. [19]
  Yuanjin Chen , Xianghui Shi , Dajiang Huang , Junnian Wei , Zhenfeng Xi . Synthesis and reactivity of cobalt dinitrogen complex supported by nonsymmetrical pincer ligand. Chinese Chemical Letters, 2024, 35(7): 109292-. doi: 10.1016/j.cclet.2023.109292
20. [20]
  Peng Meng , Qian-Cheng Luo , Aidan Brock , Xiaodong Wang , Mahboobeh Shahbazi , Aaron Micallef , John McMurtrie , Dongchen Qi , Yan-Zhen Zheng , Jingsan Xu . Molar ratio induced crystal transformation from coordination complex to coordination polymers. Chinese Chemical Letters, 2024, 35(4): 108542-. doi: 10.1016/j.cclet.2023.108542

Get Citation

PDF

XML

Metrics

PDF Downloads(18)
Abstract views(787)
HTML views(99)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142