Citation: Chao Peng, Wenting Liang, Jiecheng Ji, Chunying Fan, Kuppusamy Kanagaraj, Wanhua Wu, Guo Cheng, Dan Su, Zhihui Zhong, Cheng Yang. Pyrene-tiaraed pillar[5]arene: Strong intramolecular excimer emission applicable for photo-writing[J]. Chinese Chemical Letters, ;2021, 32(1): 345-348. doi: 10.1016/j.cclet.2020.03.079 shu

Pyrene-tiaraed pillar[5]arene: Strong intramolecular excimer emission applicable for photo-writing

Chao Peng ^a ,
Wenting Liang ^b ,
Jiecheng Ji ^{a, c} ,
Chunying Fan ^a ,
Kuppusamy Kanagaraj ^a ,
Wanhua Wu ^{a, *,} ,
Guo Cheng ^a ,
Dan Su ^a ,
Zhihui Zhong ^a ,
Cheng Yang ^{a, *,}

a.
Key Laboratory of Green Chemistry & Technology, College of Chemistry and Healthy Food Evaluation Research Center, Sichuan University, Chengdu 610064, China
b.
Institute of Environmental Science, Department of Chemistry, Shanxi University, Taiyuan 030006, China
c.
Huaxi MR Research Center (HMRRC), Department of Radiology, West China Hospital, Sichuan University, Chengdu 610041, China

wuwanhua@scu.edu.cn

yangchengyc@scu.edu.cn

Received Date: 6 February 2020
Revised Date: 10 March 2020
Accepted Date: 31 March 2020
Available Online: 9 April 2020

Figures(5)

A pyrene-tiaraed pillar[5]arene derivative was synthesized, which showed a concentration-independent intensive excimer emission. Photolysis of the pyrene-tiaraed pillar[5]arene led to a switch from excimer to monomer emission, applicable to photo-writing.
- Pillar[n]arenes,
- Pyrene,
- Excimer,
- Photo-writing
1. [1]
  T. Ogoshi, T.A. Yamagishi, Y. Nakamoto, Chem. Rev. 116 (2016) 7937-8002. doi: 10.1021/acs.chemrev.5b00765
2. [2]
  J.R. Wu, A.U. Mu, B. Li, et al., Angew. Chem. Int. Ed. 57 (2018) 9853-9858. doi: 10.1002/anie.201805980
3. [3]
  W.B. Hu, H.M. Yang, W.J. Hu, et al., Chem. Commun. 50 (2014) 10460-10463. doi: 10.1039/C4CC01810A
4. [4]
  B. Jiang, W. Wang, Y. Zhang, et al., Angew. Chem. Int. Ed. 56 (2017) 14438-14442. doi: 10.1002/anie.201707209
5. [5]
  C. Li, K. Han, J. Li, et al., Org. Lett. 14 (2012) 42-45. doi: 10.1021/ol2027834
6. [6]
  J.C. Gui, Z.Q. Yan, Y. Peng, et al., Chin. Chem. Lett. 27 (2016) 1017-1021. doi: 10.1016/j.cclet.2016.04.021
7. [7]
  X.B. Hu, Z. Chen, L. Chen, et al., Chem. Commun. 48 (2012) 10999-11001. doi: 10.1039/c2cc36027f
8. [8]
  Y. Wang, J.F. Xu, Y.Z. Chen, et al., Chem. Commun. 50 (2014) 7001-7003. doi: 10.1039/C4CC02760D
9. [9]
  N.L. Strutt, R.S. Forgan, J.M. Spruell, et al., J. Am. Chem. Soc. 133 (2011) 5668-5671. doi: 10.1021/ja111418j
10. [10]
  N. Cheng, Y. Chen, X. Wu, et al., Chem. Commun. 54 (2018) 6284-6287. doi: 10.1039/C8CC03306D
11. [11]
  L. Chen, W. Si, L. Zhang, et al., J. Am. Chem. Soc. 135 (2013) 2152-2155. doi: 10.1021/ja312704e
12. [12]
  L. Ma, S. Wang, C. Li, et al., Chem. Commun. 54 (2018) 2405-2408. doi: 10.1039/C8CC00213D
13. [13]
  J. Chen, H. Ni, Z. Meng, et al., Nat. Commun. 10 (2019) 3546. doi: 10.1038/s41467-019-11553-7
14. [14]
  W.B. Hu, Z. Wang, X.L. Zhao, et al., Chem. Eur. J. 25 (2019) 2189-2194.
15. [15]
  J. Ji, Y. Li, C. Xiao, et al., Chem. Commun. 56 (2020) 161-164. doi: 10.1039/C9CC08541F
16. [16]
  C. Fan, J. Yao, G. Li, et al., Chem. Eur. J. 25 (2019) 12526-12537. doi: 10.1002/chem.201902676
17. [17]
  K. Yang, S. Chao, F. Zhang, et al., Chem. Commun. 55 (2019) 13198-13210. doi: 10.1039/C9CC07373F
18. [18]
  J. Yao, W. Wu, W. Liang, et al., Angew. Chem. Int. Ed. 56 (2017) 6869-6873. doi: 10.1002/anie.201702542
19. [19]
  L. Chen, Y. Cai, W. Feng, et al., Chem. Commun. 55 (2019) 7883-7898. doi: 10.1039/C9CC03292D
20. [20]
  Q. Zhao, Y. Chen, B. Sun, et al., Eur. J. Org. Chem. (2019) (2019) 3396-3400.
21. [21]
  R. Zhang, X. Yan, H. Guo, et al., Chem. Commun. 56 (2020) 948-951. doi: 10.1039/C9CC09155F
22. [22]
  B. Hua, L. Shao, Z. Zhang, et al., J. Am. Chem. Soc. 141 (2019) 15008-15012. doi: 10.1021/jacs.9b08257
23. [23]
  Y. Zhu, L. Xu, L. Wang, et al., Chem. Commun. 55 (2019) 5910-5913. doi: 10.1039/C9CC02585E
24. [24]
  H. Zhang, X. Ma, J. Guo, et al., RSC Adv. 3 (2013) 368-371. doi: 10.1039/C2RA22123C
25. [25]
  S. Sun, X.Y. Hu, D. Chen, et al., Polym. Chem. 4 (2013) 2224-2229. doi: 10.1039/c3py00162h
26. [26]
  B. Hua, L. Shao, G. Yu, et al., Chem. Commun. 52 (2016) 10016-10019. doi: 10.1039/C6CC04919B
27. [27]
  H. Wang, C.N. Zhu, H. Zeng, et al., Adv. Mater. 31 (2019) 1807328. doi: 10.1002/adma.201807328
28. [28]
  C. Fan, W. Wu, J.J. Chruma, et al., J. Am. Chem. Soc. 138 (2016) 15405-15412. doi: 10.1021/jacs.6b07946
29. [29]
  L.B. Meng, D. Li, S. Xiong, et al., Chem. Commun. 51 (2015) 4643-4646. doi: 10.1039/C5CC00398A
30. [30]
  M. Hao, G. Sun, M. Zuo, et al., Angew. Chem. Int. Ed. 58 (2019) 2-8. doi: 10.1002/anie.201813331
31. [31]
  K. Jie, M. Liu, Y. Zhou, et al., J. Am. Chem. Soc. 139 (2017) 2908-2911. doi: 10.1021/jacs.6b13300
32. [32]
  T. Ogoshi, R. Sueto, Y. Hamada, et al., Chem. Commun. 53 (2017) 8577-8580. doi: 10.1039/C7CC04454B
33. [33]
  K. Jie, Y. Zhou, E. Li, et al., J. Am. Chem. Soc. 140 (2018) 3190-3193. doi: 10.1021/jacs.7b13156
34. [34]
  Y. Li, Y. Shu, X. Wang, et al., Chem. Commun. 55 (2019) 6301-6304. doi: 10.1039/C9CC02352F
35. [35]
  S. Sarkar, S. Roy, A. Sikdar, et al., Analyst 138 (2013) 7119-7126. doi: 10.1039/c3an00928a
36. [36]
  S. Long, Q. Qiao, F. Deng, et al., Chem. Commun. 55 (2019) 969-972. doi: 10.1039/C8CC09544B
37. [37]
  J.B. Birks, L.G. Christophorou, Spectrochim. Acta 19 (1963) 401-410. doi: 10.1016/0371-1951(63)80051-X
38. [38]
  P. Wanat, R. Kasprzyk, M. Kopcial, et al., Chem. Commun. 54 (2018) 9773-9776. doi: 10.1039/C8CC04968H
39. [39]
  T.M. Figueira-Duarte, K. Müllen, Chem. Rev. 111 (2011) 7260-7314. doi: 10.1021/cr100428a
40. [40]
  J. Wu, W. Liang, T. Niu, et al., Chem. Commun. 54 (2018) 9206-9209. doi: 10.1039/C8CC03660H
41. [41]
  M. Nakamura, M. Fukuda, T. Takada, et al., Org. Biomol. Chem. 10 (2012) 9620-9626. doi: 10.1039/c2ob26773j
42. [42]
  H.J. Kim, J. Hong, A. Hong, et al., Org. Lett. 10 (2008) 1963-1966. doi: 10.1021/ol800475d
43. [43]
  P. Conlon, C.J. Yang, Y. Wu, et al., J. Am. Chem. Soc. 130 (2008) 336-342. doi: 10.1021/ja076411y
44. [44]
  K. Kawai, H. Yoshida, T. Takada, et al., J. Phys. Chem. B 108 (2004) 13547-13550. doi: 10.1021/jp049543b
45. [45]
  B. Schazmann, N. Alhashimy, D. Diamond, J. Am. Chem. Soc. 128 (2006) 8607-8614. doi: 10.1021/ja061917m
46. [46]
  Z. Zhao, S. Chen, J.W. Y. Lam, et al., J. Mater. Chem. 21 (2011) 7210-7216. doi: 10.1039/c0jm04449k
47. [47]
  J.S. Yang, C.S. Lin, C.Y. Hwang, Org. Lett. 3 (2001) 889-892. doi: 10.1021/ol015524y
48. [48]
  S. Karuppannan, J.C. Chambron, Chem. Asian J. 6 (2011) 964-984. doi: 10.1002/asia.201000724
49. [49]
  X.L. Ni, S. Wang, X. Zeng, et al., Org. Lett. 13 (2011) 552-555. doi: 10.1021/ol102914t
50. [50]
  J. Cho, T. Pradhan, J.S. Kim, et al., Org. Lett. 15 (2013) 4058-4061. doi: 10.1021/ol401469z
51. [51]
  J. Huang, Y. Wu, Y. Chen, et al., Angew. Chem. Int. Ed. 50 (2011) 401-404. doi: 10.1002/anie.201005375
52. [52]
  J. Ji, W. Wu, W. Liang, et al., J. Am. Chem. Soc. 141 (2019) 9225-9238. doi: 10.1021/jacs.9b01993
53. [53]
  X. Wei, W. Wu, R. Matsushita, et al., J. Am. Chem. Soc. 140 (2018) 3959-3974. doi: 10.1021/jacs.7b12085
54. [54]
  J. Yao, Z. Yan, J. Ji, et al., J. Am. Chem. Soc. 136 (2014) 6916-6919. doi: 10.1021/ja5032908
55. [55]
  Z. Yan, Q. Huang, W. Liang, et al., Org. Lett. 19 (2017) 898-901. doi: 10.1021/acs.orglett.7b00057
56. [56]
  M. Rao, K. Kanagaraj, C. Fan, et al., Org. Lett. 20 (2018) 1680-1683. doi: 10.1021/acs.orglett.8b00520
57. [57]
  H. Lai, T. Zhao, Y. Deng, et al., Chin. Chem. Lett. 30 (2019) 1979-1983. doi: 10.1016/j.cclet.2019.09.009
58. [58]
  J. Yi, W. Liang, X. Wei, et al., Chin. Chem. Lett. 29 (2018) 87-90. doi: 10.1016/j.cclet.2017.05.004
59. [59]
  J. Ding, J. Chen, W. Mao, et al., Org. Biomol. Chem. 15 (2017) 7894-7897. doi: 10.1039/C7OB02013A
60. [60]
  M. Guo, X. Wang, C. Zhan, et al., J. Am. Chem. Soc. 140 (2018) 74-77. doi: 10.1021/jacs.7b10767
61. [61]
  D. Niu, Y. Jiang, L. Ji, et al., Angew. Chem. Int. Ed. 58 (2019) 5946-5950. doi: 10.1002/anie.201900607
62. [62]
  J.K. Choi, S.H. Kim, J. Yoon, et al., J. Org. Chem. 71 (2006) 8011-8015. doi: 10.1021/jo060981j
63. [63]
  P.L. Piciulo, J.K. Thomas, J. Chem. Phys. 68 (1978) 3260-3264. doi: 10.1063/1.436130
64. [64]
  C.D. Borsarelli, H.A. Montejano, J.J. Cosa, et al., J. Photochem. Photobiol. A: Chem. 91 (1995) 13-19. doi: 10.1016/1010-6030(95)04124-X
65. [65]
  T.L. Gilchrist, G.E. Gymer, Adv. Heterocycl. Chem. 16 (1974) 33-85.
66. [66]
  G. Maier, J. Eckwert, A. Bothur, et al., Liebigs. Ann. (1996) (1996) 1041-1053.
67. [67]
  N.A. Al-Jalal, N.A. Al-Awadi, M.R. Ibrahim, et al., Intl. J. Chem. 5 (2013) 80.
68. [68]
  J. Lin, S. Wan, W. Liu, et al., Chem. Commun. 55 (2019) 4299-4302. doi: 10.1039/C9CC01388A
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