Citation: Lai Hongxia, Zhao Ting, Deng Yurong, Fan Chunyin, Wu Wanhua, Yang Cheng. Assembly-enhanced triplet-triplet annihilation upconversion in the aggregation formed by Schiff-base Pt(II) complex grafting-permethyl-β-CD and 9, 10-diphenylanthracence dimer[J]. Chinese Chemical Letters, ;2019, 30(11): 1979-1983. doi: 10.1016/j.cclet.2019.09.009 shu

Assembly-enhanced triplet-triplet annihilation upconversion in the aggregation formed by Schiff-base Pt(II) complex grafting-permethyl-β-CD and 9, 10-diphenylanthracence dimer

Key Laboratory of Green Chemistry & Technology, College of Chemistry and Healthy Food Evaluation Research Center, Sichuan University, Chengdu 610064, China

wuwanhua@scu.edu.cn

yangchengyc@scu.edu.cn

Received Date: 10 July 2019
Revised Date: 29 August 2019
Accepted Date: 6 September 2019
Available Online: 9 November 2019

Figures(6)

Water-soluble triplet sensitizer with permethyl-β-cyclodextrin (PMCD) grafting on a Schiff-base Pt (II) complex (Pt-2), in which PMCD unit serves as a host for binding the acceptors and the Schiff-base Pt(II) complex serves as a triplet sensitizer, was synthesized to investigate the effect of supramolecular complexation and assembly on the triplet-triplet annihilation upconversion emission in water. 9, 10-Diphenylanthracence (DPA) carboxylate (A-1) and its dimer (A-2) in which two DPA carboxylate were covalently linked with an alkyl chain were synthesized as triplet acceptors which also play a role of guest molecules for PMCD. A-1 and A-2 showed high affinity with PMCD, and A-2 can readily aggregate in water and form micron sized assemblies due to the hydrophobic effect and π-π stacking of anthracene core in A-2. The efficiency of TTA-UC was demonstrated to be enhanced by a synergistic effect of host-guest complexation of Pt-2 with A-2 and the self-aggregation of the acceptor A-2, which facilitated the energy transfer and energy fusion among donor and acceptor.
- Triplet-triplet annihilation upconversion,
- Host-guest interactions,
- Self-aggregation,
- Permethyl-β-CD
1. [1]
  Y.Y. Cheng, B. Fückel, R.W. MacQueen, et al., Energy Environ. Sci. 5 (2012) 6953-6959. doi: 10.1039/c2ee21136j
2. [2]
  A. Monguzzi, D. Braga, M. Gandini, et al., Nano Lett. 14 (2014) 6644-6650. doi: 10.1021/nl503322a
3. [3]
  J. Wang, Y. Lu, N. McGoldrick, et al., J. Mater. Chem. C 4 (2016) 6131-6139.
4. [4]
  O.S. Kwon, H.S. Song, J.O. Conde, et al., ACS Nano 10 (2016) 1512-1521. doi: 10.1021/acsnano.5b07075
5. [5]
  J.I. Goldsmith, W.R. Hudson, M.S. Lowry, et al., J. Am. Chem. Soc. 127 (2005) 7502-7510. doi: 10.1021/ja0427101
6. [6]
  R.R. Islangulov, F.N. Castellano, Angew. Chem. Int. Ed. 45 (2006) 5957-5959. doi: 10.1002/anie.200601615
7. [7]
  O.S. Wenger, Chem.-Eur. J. 17 (2011) 11692-11702. doi: 10.1002/chem.201102011
8. [8]
  M. Rao, K. Kanagaraj, C. Fan, et al., Org. Lett. 20 (2018) 1680-1683. doi: 10.1021/acs.orglett.8b00520
9. [9]
  C.H. Chen, N.T. Tierce, M.K. Leung, et al., Adv. Mater. 30 (2018) 1804850.
10. [10]
  W. Xu, W. Liang, W. Wu, et al., Chem.-Eur. J. 24 (2018) 16677-16685. doi: 10.1002/chem.201804001
11. [11]
  T.N. Singh-Rachford, F.N. Castellano, Coord. Chem. Rev. 254 (2010) 2560-2573. doi: 10.1016/j.ccr.2010.01.003
12. [12]
  C. Ye, L. Zhou, X. Wang, et al., PCCP 18 (2016) 10818-10835. doi: 10.1039/C5CP07296D
13. [13]
  T. Ogawa, M. Hosoyamada, B. Yurash, et al., J. Am. Chem. Soc. 140 (2018) 8788-8796. doi: 10.1021/jacs.8b04542
14. [14]
  P. Bharmoria, S. Hisamitsu, H. Nagatomi, et al., J. Am. Chem. Soc. 140 (2018) 10848-10855. doi: 10.1021/jacs.8b05821
15. [15]
  Y. Che, W. Yang, G. Tang, et al., J. Mater. Chem. C 6 (2018) 5785-5793. doi: 10.1039/C8TC00513C
16. [16]
  Y. Bai, J.H. Olivier, H. Yoo, et al., J. Am. Chem. Soc. 139 (2017) 16946-16958. doi: 10.1021/jacs.7b09982
17. [17]
  Z. Wang, J. Zhao, A. Barbon, et al., J. Am. Chem. Soc. 139 (2017) 7831-7842. doi: 10.1021/jacs.7b02063
18. [18]
  H. Jia, B. Küçüköz, Y. Xing, et al., J. Mater. Chem. C 2 (2014) 9720-9736. doi: 10.1039/C4TC01675K
19. [19]
  W. Wu, J. Zhao, J. Sun, et al., J. Mater. Chem. C 1 (2013) 705-716. doi: 10.1039/C2TC00214K
20. [20]
  J. Park, M. Xu, F. Li, et al., J. Am. Chem. Soc. 140 (2018) 5493-5499. doi: 10.1021/jacs.8b01613
21. [21]
  H. Kouno, T. Ogawa, S. Amemori, et al., Chem. Sci. 7 (2016) 5224-5229. doi: 10.1039/C6SC01047D
22. [22]
  K. Tanaka, K. Inafuku, Y. Chujo, Chem. Commun. 46 (2010) 4378-4380. doi: 10.1039/c0cc00266f
23. [23]
  Q. Liu, M. Xu, T. Yang, et al., ACS Appl. Mater. Interface 10 (2018) 9883-9888.
24. [24]
  C. Kerzig, O.S. Wenger, Chem. Sci. 9 (2018) 6670-6678. doi: 10.1039/C8SC01829D
25. [25]
  H. Kouno, Y. Sasaki, N. Yanai, et al., Chem.-Eur. J. 25 (2019) 6124-6130. doi: 10.1002/chem.201806076
26. [26]
  H.Q. Peng, L.Y. Niu, Y.Z. Chen, et al., Chem. Rev. 115 (2015) 7502-7542. doi: 10.1021/cr5007057
27. [27]
  C. Fan, W. Wu, J.J. Chruma, et al., J. Am. Chem. Soc. 138 (2016) 15405-15412. doi: 10.1021/jacs.6b07946
28. [28]
  M.V. Rekharsky, Y. Inoue, Chem. Rev. 98 (1998) 1875-1918. doi: 10.1021/cr970015o
29. [29]
  X. Yu, W. Liang, Q. Huang, et al., Chem. Commun. 55 (2019) 3156-3159. doi: 10.1039/C9CC00097F
30. [30]
  J. Ji, W. Wu, W. Liang, et al., J. Am. Chem. Soc. 141 (2019) 9225-9238. doi: 10.1021/jacs.9b01993
31. [31]
  X. Wei, W. Wu, R. Matsushita, et al., J. Am. Chem. Soc. 140 (2018) 3959-3974. doi: 10.1021/jacs.7b12085
32. [32]
  J. Yi, W. Liang, X. Wei, et al., Chin. Chem. Lett. 29 (2018) 87-90. doi: 10.1016/j.cclet.2017.05.004
33. [33]
  Z. Yan, Q. Huang, W. Liang, et al., Org. Lett. 19 (2017) 898-901. doi: 10.1021/acs.orglett.7b00057
34. [34]
  Z.Y. Gu, D.S. Guo, M. Sun, et al., J. Org. Chem. 75 (2010) 3600-3607. doi: 10.1021/jo100351f
35. [35]
  Z.Q. Li, Y.M. Zhang, D.S. Guo, et al., Chem.-Eur. J. 19 (2013) 96-100. doi: 10.1002/chem.201203575
36. [36]
  Y. Yang, Y.M. Zhang, Y. Zhang, et al., Chem. Asian J. 10 (2015) 84-90. doi: 10.1002/asia.201402802
37. [37]
  G. Liu, X. Xu, Y. Chen, et al., Chem. Commun. 52 (2016) 7966-7969. doi: 10.1039/C6CC02996E
38. [38]
  X. Chen, Y.N. Wang, R.X. Rong, et al., Dyes Pigm. 160 (2019) 779-786. doi: 10.1016/j.dyepig.2018.09.011
39. [39]
  R. Liu, Y. Zhang, W. Wu, et al., Chin. Chem. Lett. 30 (2019) 577-581. doi: 10.1016/j.cclet.2018.12.002
40. [40]
  Q. Huang, L. Jiang, W. Liang, et al., J. Org. Chem. 81 (2016) 3430-3434. doi: 10.1021/acs.joc.6b00130
41. [41]
  C. Yang, Q. Wang, M. Yamauchi, et al., Photochem. Photobiol. Sci. 13 (2014) 190-198. doi: 10.1039/C3PP50255D
42. [42]
  M. Nishijima, M. Goto, M. Fujikawa, et al., Chem. Commun. 50 (2014) 14082-14085. doi: 10.1039/C4CC04818K
43. [43]
  J. Yao, Z. Yan, J. Ji, et al., J. Am. Chem. Soc. 136 (2014) 6916-6919. doi: 10.1021/ja5032908
44. [44]
  W. Liang, C. Yang, D. Zhou, et al., Chem. Commun. 49 (2013) 3510-3512. doi: 10.1039/c3cc40542g
45. [45]
  L. Dai, W. Wu, W. Liang, et al., Chem. Commun. 54 (2018) 2643-2646. doi: 10.1039/C8CC00840J
46. [46]
  X. Wei, X. Yu, Y. Zhang, et al., J. Photochem. Photobio. A:Chem. 371 (2019) 374-381. doi: 10.1016/j.jphotochem.2018.11.038
47. [47]
  M. Rao, W. Wu, C. Yang, Molecules 24 (2019) 1502.
48. [48]
  N. Kimizuka, N. Yanai, M.A. Morikawa, Langmuir 32 (2016) 12304-12322. doi: 10.1021/acs.langmuir.6b03363
49. [49]
  N. Yanai, N. Kimizuka, Chem. Commun. 52 (2016) 5354-5370. doi: 10.1039/C6CC00089D
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