Citation: He Zihan, Li Wenbo, Chen Gan, Zhang Yongming, Yuan Wang-Zhang. Polymorphism dependent triplet-involved emissions of a pure organic luminogen[J]. Chinese Chemical Letters, ;2019, 30(4): 933-936. doi: 10.1016/j.cclet.2019.03.015 shu

Polymorphism dependent triplet-involved emissions of a pure organic luminogen

School of Chemistry and Chemical Engineering, Shanghai Key Lab of Electrical Insulation and Thermal Aging, Shanghai Electrochemical Energy Devices Research Center, Shanghai Jiao Tong University, Shanghai 200240, China

ymzhang@sjtu.edu.cn

wzhyuan@sjtu.edu.cn

Received Date: 28 February 2019
Revised Date: 6 March 2019
Accepted Date: 7 March 2019
Available Online: 8 April 2019

Figures(5)

Polymorphism has been frequently used in tuning the singlet emissions of pure organic dyes. The modulation of triplet-involved emissions, particularly room temperature phosphorescence (RTP), however, is scarcely reported. Herein, polymorphism is reported to tune the triplet-involved emissions of 2CZBZL, a newly designed pure organic luminogen consisting of twisted benzil and two planar carbazole moieties. Other than the conventional modulation through changing molecular conformation and packing, vibration can also finely tune the triplet-involved emissions. Besides prompt fluorescence (PF), polymorph B with relatively extended conformation emits thermally activated delayed fluorescence (TADF), whereas the others (A, C-E) with similarly more twisted conformations generate predominant RTP or simultaneous DF and RTP. These results demonstrate the fascinating chance to regulate the tripletinvolved emissions through controlling conformation and vibration.
- Polymorphism,
- Room temperature phosphorescence,
- Pure organic luminogens,
- Thermally activated delayed fluorescence,
- Triplet-involved emissions
1. [1]
  Z. Song, W. Zhang, M. Jiang, et al., Adv. Funct. Mater. 26(2016) 824-832. doi: 10.1002/adfm.v26.6
2. [2]
  O. Bolton, K. Lee, H.J. Kim, K.Y. Lin, J. Kim, Nat. Chem. 3(2011) 205-210. doi: 10.1038/nchem.984
3. [3]
  W. Huang, L. Sun, Z. Zheng, J. Su, H. Tian, Chem. Commun. 51(2015) 4462-4464. doi: 10.1039/C4CC09613D
4. [4]
  C. Yuan, S. Saito, C. Camacho, et al., J. Am. Chem. Soc. 135(2013) 8842-8845. doi: 10.1021/ja404198h
5. [5]
  J. Yang, Z. Ren, B. Chen, et al., J. Mater. Chem. C 5(2017) 9242-9246. doi: 10.1039/C7TC03656F
6. [6]
  D. Yan, D.G. Evans, Mater. Horiz. 1(2014) 46-57. doi: 10.1039/C3MH00023K
7. [7]
  Y. Zhang, H. Ma, S. Wang, et al., J. Phys. Chem. C 120(2016) 19759-19767. doi: 10.1021/acs.jpcc.6b05537
8. [8]
  T. Mutai, H. Satou, K. Araki, Nat. Mater. 4(2005) 685-687. doi: 10.1038/nmat1454
9. [9]
  K. Wang, H. Zhang, S. Chen, et al., Adv. Mater. 26(2014) 6168-6173. doi: 10.1002/adma.201401114
10. [10]
  G. Zhang, J. Lu, M. Sabat, C.L. Fraser, J. Am. Chem. Soc. 132(2010) 2160-2162. doi: 10.1021/ja9097719
11. [11]
  W. Luo, Y. Zhang, Y. Gong, et al., Chin. Chem. Lett. 29(2018) 1533-1536. doi: 10.1016/j.cclet.2018.08.001
12. [12]
  X. Fang, D. Yan, Sci. China Chem. 61(2018) 397-401. doi: 10.1007/s11426-017-9183-9
13. [13]
  X. Li, S. Semin, L.A. Estrada, et al., Chin. Chem. Lett. 29(2018) 297-300. doi: 10.1016/j.cclet.2017.11.001
14. [14]
  C. Wang, B. Xu, M. Li, et al., Mater. Horiz. 3(2016) 220-225. doi: 10.1039/C6MH00025H
15. [15]
  M. Brinkmann, G. Gadret, M. Muccini, et al., J. Am. Chem. Soc.122(2000) 5147-5157. doi: 10.1021/ja993608k
16. [16]
  H. Liu, X. Cheng, Z. Bian, K. Ye, H. Zhang, Chin. Chem. Lett. 29(2018) 1537-1540. doi: 10.1016/j.cclet.2018.08.003
17. [17]
  H. Wu, W. Chi, G. Baryshnikov, et al., Angew. Chem. Int. Ed. 58 (2019), doi: http://dx.doi.org/10.1002/anie.201900703.
18. [18]
  M.A. El-Sayed, Acc. Chem. Res. 1(1968) 8-16. doi: 10.1021/ar50001a002
19. [19]
  N.J. Turro, V. Ramamurthy, J.C. Scaiano, Modern Molecular Photochemistry of Organic Molecules, University Science Books, Sausalito, CA, 2010.
20. [20]
  C. Wang, Y. Gong, W.Z. Yuan, Y. Zhang, Chin. Chem. Lett. 27(2016) 1184-1192. doi: 10.1016/j.cclet.2016.05.026
21. [21]
  S. Hirata, Adv. Opt. Mater. 5(2017)1700116. doi: 10.1002/adom.201700116
22. [22]
  M. Baroncini, G. Bergamini, P. Ceroni, Chem. Commun. 53(2017) 2081-2093. doi: 10.1039/C6CC09288H
23. [23]
  W.Z. Yuan, X.Y. Shen, H. Zhao, et al., J. Phys. Chem. C 114(2010) 6090-6099. doi: 10.1021/jp909388y
24. [24]
  Y. Xie, Y. Ge, Q. Peng, et al., Adv. Mater. 29(2017) 1606829. doi: 10.1002/adma.v29.17
25. [25]
  W. Zhao, Z. He, J.W.Y. Lam, et al., Chemistry 1(2016) 592-602. doi: 10.1016/j.chempr.2016.08.010
26. [26]
  J. Wang, X. Gu, H. Ma, et al., Nat. Commun. 9(2018) 2963. doi: 10.1038/s41467-018-05298-y
27. [27]
  S. Hirata, J. Mater. Chem. C 6(2018) 11785-11794. doi: 10.1039/C8TC01417E
28. [28]
  M. Shimizu, R. Shigitani, M. Nakatani, J. Phys. Chem. C 120(2016) 11631-11639. doi: 10.1021/acs.jpcc.6b03276
29. [29]
  Z. An, C. Zheng, Y. Tao, et al., Nat. Mater. 14(2015) 685-690. doi: 10.1038/nmat4259
30. [30]
  L. Bian, H. Shi, X. Wang, et al., J. Am. Chem. Soc. 140(2018) 10734-10739. doi: 10.1021/jacs.8b03867
31. [31]
  H. Ma, Q. Peng, Z. An, W. Huang, Z. Shuai, J. Am. Chem. Soc. 141(2019) 1010-1015. doi: 10.1021/jacs.8b11224
32. [32]
  D. Li, F. Lu, J. Wang, et al., J. Am. Chem. Soc. 140(2018) 1916-1923. doi: 10.1021/jacs.7b12800
33. [33]
  L. Xu, G. Li, T. Xu, et al., Chem. Commun. 54(2018) 9226-9229. doi: 10.1039/C8CC04734K
34. [34]
  Y. Gong, G. Chen, Q. Peng, et al., Adv. Mater. 27(2015) 6195-6201. doi: 10.1002/adma.201502442
35. [35]
  W.X. Wu, H. Wang, W.J. Jin, Cryst. Growth Des. 18(2018) 6742-6747. doi: 10.1021/acs.cgd.8b01021
36. [36]
  Z. Yang, Z. Mao, X. Zhang, et al., Angew. Chem. Int. Ed. 55(2016) 2181-2185. doi: 10.1002/anie.201509224
37. [37]
  H. Wu, Y. Zhou, L. Yin, et al., J. Am. Chem. Soc. 139(2017) 785-791. doi: 10.1021/jacs.6b10550
38. [38]
  H. Wua, B. Wu, X. Yu, et al., Chin. Chem. Lett. 28(2017) 2151-2154. doi: 10.1016/j.cclet.2017.08.002
39. [39]
  H. Uoyama, K. Goushi, K. Shizu, H. Nomura, C. Adachi, Nature 492(2012) 234-238. doi: 10.1038/nature11687
40. [40]
  Y. Tao, K. Yuan, T. Chen, Adv. Mater. 26(2014) 7931-7958. doi: 10.1002/adma.v26.47
41. [41]
  Z. Yang, Z. Mao, Z. Xie, et al., Chem. Soc. Rev. 46(2017) 915-1016. doi: 10.1039/C6CS00368K
42. [42]
  J.S. Ward, R.S. Nobuyasu, A.S. Batsanov, et al., Chem. Commun. 52(2016) 2612-2615. doi: 10.1039/C5CC09645F
43. [43]
  M. Pope, C.E. Swenberg, Electronic Processes in Organic Crystals and Polymers, Oxford University Press, Oxford, 1999.
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