Citation: ZHANG Jie, TENG Ming-Yu, DAI Guo-Liang, ZHAO Song-Lin, WANG Jia-Li, ZHANG Ping, SONG Tong-Tong. Synthesis, Characterization, Linear and Nonlinear Optical Effects of Nonsymmetrical Bipolar (D-π-A) Pyridyl Metallo Salophen Complexes[J]. Chinese Journal of Inorganic Chemistry, ;2014, 30(3): 499-505. doi: 10.11862/CJIC.2014.059 shu

Synthesis, Characterization, Linear and Nonlinear Optical Effects of Nonsymmetrical Bipolar (D-π-A) Pyridyl Metallo Salophen Complexes

1.
1 School of Pharmaceutical and Chemical Engineering, Taizhou University, Taizhou, Zhejiang 318000, China;

Received Date: 29 July 2013
Available Online: 26 September 2013
Fund Project: 浙江省自然科学基金(No.LQ13B010001) (No.LQ13B010001)国家自然科学基金(No.21203135) (No.21203135)浙江省教育厅科研基金(No.Y201016505)资助项目。 (No.Y201016505)

The pyridine substituent vanillins (1a and 1b) were synthesized by still coupling reaction. New unsymmetrical metallo Salophen complexes (3a, 3b and 3c) derived from the condensation of monoamine 2 and pyridine substituent salicylaldehyde in the presence of transition metal ions (Zn²⁺, Ni²⁺) as template have been synthesized and characterized. The linear and third-order non-linear optical (two photon absorption, TPA) properties of the complexes have been measured. The emission of (3a and 3c) were in the visible range(504~516 nm) with lifetime between 4.51 to 5.18 ns and quantum yields (Φ_em) between 4.3% to 5.3%. Decay times with nano-second scale indicate the emissions come from the singlet states. Complexes 3a, 3b and 3c are thermally stable with onset decomposition temperatures (T_d) within the range of 333 to 374 ℃. 100 fs laser pulses with the open-aperture Z-scan method was used to measure the TPA cross-sections σ⁽²⁾ of 3a, 3b and 3c at 800 nm. The σ⁽²⁾ could reach to 1 403 GM, which is among the largest value known for metalloSalophen complexes to date. In general, these Salophen complexes show moderate fluorescence quantum yields, larger σ⁽²⁾, low cytotoxicity of zinc complexes and thermal stability. Hence, they are potentially good TPA candidates for tissue imaging work and excitation by NIR or longer-wavelength radiation is possible to increase penetration depth and reduce cell damage.
- Salophen complexes;bipolar molecular;linear optical properties;two photon absorption cross-sections;Z-scan
1. [1]
  [1] Xing G C, Liao Y L, Wu X Y, et al. Acs Nano, 2012,6(12):10835-10844
2. [2]
  [2] Dai J, Fu Z C, Lan S, et al. J. Appl. Phys., 2012,112:063102
3. [3]
  [3] Zhang C, Zou C L, Yan Y L, et al. J. Am. Chem. Soc., 2011, 133(19):7276-7279
4. [4]
  [4] del Valle E, Zippilli S, Laussy F P, et al. Phys. Rev. B, 2010,81(3):035302
5. [5]
  [5] Belfield K D, Bondar M V, Yanez C O, et al. J. Mater. Chem., 2009,19(40):7498-7502
6. [6]
  [6] Lott J, Ryan C, Valle B, et al. Adv. Mater., 2011,23(21): 2425-2429
7. [7]
  [7] Iliopoulos K, Krupka O, Gindre D, et al. J. Am. Chem. Soc., 2010,132(41):14343-143145
8. [8]
  [8] Corredor C C, Huang Z L, Belfield K D, et al. Chem. Mater., 2007,19(21):5165-5173
9. [9]
  [9] Garcia G, Hammerer F, Poyer F, et al. Biorg. Med. Chem., 2013,21(1):153-165
10. [10]
  [10] Cepraga C, Gallavardin T, Marotte S, et al. Polym. Chem., 2013,4(1):61-67
11. [11]
  [11] Zhao T T, Shen X Q, Li L, et al. Nanoscale, 2012,4(24): 7712-7719
12. [12]
  [12] Fowley C, Nomikou N, McHale A P, et al. J. Mater. Chem., 2012,22(13):6456-6462
13. [13]
  [13] Bergendahl L T, Paterson M J. J. Phys. Chem. B, 2012,116 (39):11818-11828
14. [14]
  [14] Albota M, Beljonne D, Bredas J L, et al. Science, 1998,281 (5383):1653-1656
15. [15]
  [15] Odom S A, Webster S, Padilha L A, et al. J. Am. Chem. Soc., 2009,131(22):7510-7511
16. [16]
  [16] Pawlicki M, Collins H A, Denning R G, et al. Angew. Chem. Int. Edit., 2009,48(18):3244-3266
17. [17]
  [17] ZHOU Hong-Ping(周虹屏), HAO Fu-Ying(郝扶影), ZHANG Ju-Zhou(张居舟), et al. Chinese J. Inorg. Chem.(无机化学学报), 2004,20(10):1165-1171
18. [18]
  [18] WANG Xiao-Mei(王筱梅), ZHOU Yu-Fang(周玉芳), WANG Chun(王春), et al. Sci. China Ser. E(中国科学), 2002,32(1): 20-27
19. [19]
  [19] Kuimova M K, Collins H A, Balaz M, et al. Org. Biomol. Chem., 2009,7(5):889-896
20. [20]
  [20] Thorley K J, Hales J M, Anderson H L, et al. Angew. Chem. Int. Edit., 2008,47(37):7095-7098
21. [21]
  [21] LIANG Ying-Hong(梁英红), ZHONG Zeng-Pei(钟增培), LI Na(李娜). Chinese J. Org. Chem.(有机化学), 2004,24(12): 1577-1582
22. [22]
  [22] Zhang B G, Li Y J, Liu R, et al. ACS Appl. Mater. Interfaces, 2013,5(3):565-572
23. [23]
  [23] Zhao Y, Roberts G M, Greenough S E, et al. Angew. Chem. Int. Edit., 2012,51(45):11263-11266
24. [24]
  [24] Pasatoiu T D, Madalan A M, Zamfirescu M, et al. Phys. Chem. Chem. Phys., 2012,14(32):11448-11456
25. [25]
  [25] Schwich T, Cifuentes M P, Gugger P A, et al. Adv. Mater., 2011,23(12):1433-1435
26. [26]
  [26] Liu T L, Yang C, Li J F, et al. J. Lumin., 2013,134:459
27. [27]
  [27] Imakita K, Ito M, Naruiwa R, et al. Appl. Phys. Lett., 2012, 101(4):041112
28. [28]
  [28] Wang B, Wang Y C, Hua J L, et al. Chem. Eur. J., 2011,17 (9):2647-2655
29. [29]
  [29] Huang C, Sartin M M, Siegel N, et al. J. Mater. Chem., 2011,21(40):16119-16128
30. [30]
  [30] Hai Y, Chen J J, Zhao P, et al. Chem. Commun., 2011,47 (8):2435-2437
31. [31]
  [31] Ye Z H, De Boni L, Neves U M, et al. Tetrahedron Lett., 2009,50(13):1371-1373
32. [32]
  [32] Liu C G, Guan X H, Su Z M. J. Phys. Chem. C, 2011,115 (13):6024-6032
33. [33]
  [33] Trujillo A, Fuentealba M, Carrillo D, et al. Inorg. Chem., 2010,49(6):2750-2764
34. [34]
  [34] Pietrangelo A, Sih B C, Boden B N, et al. Adv. Mater., 2008,20(12):2280-2284
35. [35]
  [35] Di Bella S, Fragala I, Ledoux I, et al. Chem. Eur. J., 2001,7 (17):3738-3743
36. [36]
  [36] DiBella S, Fragala I, Ledoux I, et al. J. Am. Chem. Soc., 1997,119(40):9550-9557
37. [37]
  [37] Zhang J, Zhong C, Zhu X J, et al. Polyhedron, 2013,49(1): 121-128
38. [38]
  [38] Tanihara J, Ogawa K, Kobuke Y. J. Photoch. Photobio. A, 2006,178(2-3):140-149
39. [39]
  [39] Meech S R, Phillips D C. J. Photochem., 1983,23(2):193-217
40. [40]
  [40] Sheik-Bahae M, Said A A, Wei T H, et al. IEEE J. Quantum Electron., 1990,26(4):760-769
41. [41]
  [41] Zhao W, Palffy-Muhoray P. Appl. Phys. Lett., 1994,65(6): 673-675
42. [42]
  [42] MENG Xiang-Ru(孟祥茹), ZHAO Jin-An(赵金安), HOU Hong-Wei(侯红卫), et al. Chinese J. Inorg. Chem.(无机化学学报), 2003,19(1):16-19
43. [43]
  [43] Kim K S, Lim J M, Osuka A, et al. J. Photochem. Photobiol. C: Photochem. Rev., 2008,9(1):13-28
44. [44]
  [44] Lo W K, Wong W K, Wong W Y, et al. Inorg. Chem., 2006, 45(23):9315-9325
45. [45]
  [45] Campbell E J, Nguyen S T. Tetrahedron Lett., 2001,42(7): 1221-1225
46. [46]
  [46] Xia Q H, Ge H Q, Ye C P, et al. Chem. Rev., 2005,105(5): 1603-1662
47. [47]
  [47] Lopez J, Mintz E A, Hsu F L, et al. Tetrahedron-Asymmetr, 1998,9(21):3741-3744
48. [48]
  [48] Holbach M, Zheng X L, Burd C, et al. J. Org. Chem., 2006, 71(7):2903-2906
49. [49]
  [49] Zhang J, Zhao F C, Zhu X J, et al. J. Mater. Chem., 2012, 22:16448
50. [50]
  [50] Kleij A W, Tooke D M, Spek A L, et al. Eur. J. Inorg. Chem., 2005(22):4626-4634
51. [51]
  [51] JI Yan(吉彦), QIAN Ying(钱鹰), ZHOU Zhi-Qiang(周志强), et al. Acta Chim. Sin.(化学学报), 2011,69(20):2499-2504
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沈阳化工大学材料科学与工程学院沈阳 110142