Citation: Liu Hao, Cheng Xiao, Bian Zhengyi, Ye Kaiqi, Zhang Hongyu. Four organic crystals displaying distinctively different emission colors based on an ESIPT-active organic molecule[J]. Chinese Chemical Letters, ;2018, 29(10): 1537-1540. doi: 10.1016/j.cclet.2018.08.003 shu

Four organic crystals displaying distinctively different emission colors based on an ESIPT-active organic molecule

Liu Hao ^a ,
Cheng Xiao ^a,b ,
Bian Zhengyi ^a ,
Ye Kaiqi ^a,, ,
Zhang Hongyu ^a,,

a.
State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun 130012, China
b.
MoE Key Laboratory of Macromolecule Synthesis and Functionalization, Department of Polymer Science and Engineering, Zhejiang University, Hangzhou 310027, China

Corresponding author: Ye Kaiqi, yekq@jlu.edu.cn Zhang Hongyu, hongyuzhang@jlu.edu.cn
Received Date: 11 July 2018
Revised Date: 2 August 2018
Accepted Date: 6 August 2018
Available Online: 8 October 2018

Figures(5)

Four crystals A-D based on a structurally simple ESIPT-active molecule 4MPP were obtained by subtly controlling the crystallization conditions. Notably, crystals A and C display single emission bands, which correspond to the keto^* (K^*) and enol^* (E^*) emission, respectively. B and D exhibit dual emission with different proportion of E^*/K^* emissions while D sucessfully achieves white emssion. The distinctively different emission properties of A-D is mainly because of the change in crystal structures. In addition, A displays amplified spontaneous emission, which indicates its potential as single crystal lasers.
- Polymorph,
- ESIPT,
- Luminescent materials,
- Fluorescent single crystal,
- Amplified spontaneous emission
References
1. [1]
  (a) D. Li, H. Zhang, Y. Wang, Chem. Soc. Rev. 42(2013) 8416-8433;
  (b)Y. Xua, M. Tian, H. Zhang, et al., Chin. Chem. Lett. 29(2018) 1093-1097;
  (c)Y. Luo, Z. Lu, Y. Huang, Chin. Chem. Lett. 27(2016) 1223-1230;
  (d)M. Bio, P. Rajaputra, G. Nkepang, Y. You, J. Med. Chem. 57(2014) 3401-3409;
  (e)H. Mizuno, I. Ohnishi, H. Yanagi, F. Sasaki, S. Hotta, Adv. Mater. 24(2012) 2404-2408;
  (f)H. Liu, Y. Li, Q. Gao, Z. Liu, H. Fu, Chin. Chem. Lett. 29(2018) 209-212;
  (g)B. Tang, Z. Zhang, H. Liu, H. Zhang, Chin. Chem. Lett. 28(2017) 2129-2132;
  (h)P. Audebert, F. Miomandre, Chem. Sci. 4(2013) 575-584;
  (i)K. Nagura, S. Saito, H. Yusa, et al., J. Am. Chem. Soc. 135(2013) 10322-10325;
  (k)L. Wang, K. Ye, H. Zhang, Chin. Chem. Lett. 27(2016) 1367-1375.
2. [2]
  (a) B.K. An, S.H. Gihm, J.W. Chung, et al., J. Am. Chem. Soc. 131(2009) 3950-3957;
  (b)P. Biegger, S. Stolz, S.N. Intorp, et al., J. Org. Chem. 80(2015) 582-589.
3. [3]
  (a) M. Shimizu, R. Kaki, Y. Takeda, et al., Angew. Chem. Int. Ed. 51(2012) 4095-4099;
  (b)S.H. Liao, J.R. Shiu, S.W. Liu, et al., J. Am. Chem. Soc. 131(2009) 763-777.
4. [4]
  (a) Y. Tao, Q. Wang, C. Yang, et al., Angew. Chem. Int. Ed. 120(2008) 8224-8227;
  (b)D.H. Kim, N.S. Cho, H.Y. Oh, et al., Adv. Mater. 23(2011) 2721-2726;
  (c)H.H. Chou, C.H. Cheng, Adv. Mater. 22(2010) 2468-2471;
  (d)H. Fukagawa, T. Shimizu, H. Hanashima, et al., Adv. Mater. 24(2012) 5099-5103;
  (e)Y. Cho, J. Lee, Adv. Mater. 23(2011) 4568-4572.
5. [5]
  C. Borek, K. Hanson, P.I. Djurovich, et al., Angew. Chem. 119(2007) 1127-1130. doi: 10.1002/(ISSN)1521-3757
6. [6]
  (a) K. Wang, H. Zhang, S. Chen, et al., Adv. Mater. 26(2014) 6168-6173;
  (b)X. Cheng, F. Li, S. Han, et al., Sci. Rep. 5(2015) 9140;
  (c) T. Seki, S. Kurenuma, H. Ito, Chem.-Eur. J. 19(2013) 16214-16220;
  (d)T. Shida, T. Mutai, K. Araki, CrystEngComm 15(2013) 10179-10182;
  (e) E.Q. Procopio, M. Mauro, M. Panigati, et al., J. Am. Chem. Soc. 132(2010) 14397-14399;
  (f)M.A. Malwitz, S.H. Lim, R.L. White-Morris, et al., J. Am. Chem. Soc. 134(2012) 10885-10893.
7. [7]
  K.C. Tang, M.J. Chang, T.Y. Lin, et al., J. Am. Chem. Soc. 133(2011) 17738-17745. doi: 10.1021/ja2062693
8. [8]
  (a) T. Mutai, H. Tomoda, T. Ohkawa, Y. Yabe, K. Araki, Angew. Chem. Int. Ed. 47(2008) 9522-9524;
  (b)R. Wei, P. Song, A. Tong, J. Phys. Chem. C 117(2013) 3467-3474.
9. [9]
  H. Liu, X. Cheng, H. Zhang, Y. Wang, S. Yamaguchi, Chem. Commun. 53(2017) 7832-7835. doi: 10.1039/C7CC03758A
1. [1]
  (a) D. Li, H. Zhang, Y. Wang, Chem. Soc. Rev. 42(2013) 8416-8433;
  (b)Y. Xua, M. Tian, H. Zhang, et al., Chin. Chem. Lett. 29(2018) 1093-1097;
  (c)Y. Luo, Z. Lu, Y. Huang, Chin. Chem. Lett. 27(2016) 1223-1230;
  (d)M. Bio, P. Rajaputra, G. Nkepang, Y. You, J. Med. Chem. 57(2014) 3401-3409;
  (e)H. Mizuno, I. Ohnishi, H. Yanagi, F. Sasaki, S. Hotta, Adv. Mater. 24(2012) 2404-2408;
  (f)H. Liu, Y. Li, Q. Gao, Z. Liu, H. Fu, Chin. Chem. Lett. 29(2018) 209-212;
  (g)B. Tang, Z. Zhang, H. Liu, H. Zhang, Chin. Chem. Lett. 28(2017) 2129-2132;
  (h)P. Audebert, F. Miomandre, Chem. Sci. 4(2013) 575-584;
  (i)K. Nagura, S. Saito, H. Yusa, et al., J. Am. Chem. Soc. 135(2013) 10322-10325;
  (k)L. Wang, K. Ye, H. Zhang, Chin. Chem. Lett. 27(2016) 1367-1375.
2. [2]
  (a) B.K. An, S.H. Gihm, J.W. Chung, et al., J. Am. Chem. Soc. 131(2009) 3950-3957;
  (b)P. Biegger, S. Stolz, S.N. Intorp, et al., J. Org. Chem. 80(2015) 582-589.
3. [3]
  (a) M. Shimizu, R. Kaki, Y. Takeda, et al., Angew. Chem. Int. Ed. 51(2012) 4095-4099;
  (b)S.H. Liao, J.R. Shiu, S.W. Liu, et al., J. Am. Chem. Soc. 131(2009) 763-777.
4. [4]
  (a) Y. Tao, Q. Wang, C. Yang, et al., Angew. Chem. Int. Ed. 120(2008) 8224-8227;
  (b)D.H. Kim, N.S. Cho, H.Y. Oh, et al., Adv. Mater. 23(2011) 2721-2726;
  (c)H.H. Chou, C.H. Cheng, Adv. Mater. 22(2010) 2468-2471;
  (d)H. Fukagawa, T. Shimizu, H. Hanashima, et al., Adv. Mater. 24(2012) 5099-5103;
  (e)Y. Cho, J. Lee, Adv. Mater. 23(2011) 4568-4572.
5. [5]
  C. Borek, K. Hanson, P.I. Djurovich, et al., Angew. Chem. 119(2007) 1127-1130. doi: 10.1002/(ISSN)1521-3757
6. [6]
  (a) K. Wang, H. Zhang, S. Chen, et al., Adv. Mater. 26(2014) 6168-6173;
  (b)X. Cheng, F. Li, S. Han, et al., Sci. Rep. 5(2015) 9140;
  (c) T. Seki, S. Kurenuma, H. Ito, Chem.-Eur. J. 19(2013) 16214-16220;
  (d)T. Shida, T. Mutai, K. Araki, CrystEngComm 15(2013) 10179-10182;
  (e) E.Q. Procopio, M. Mauro, M. Panigati, et al., J. Am. Chem. Soc. 132(2010) 14397-14399;
  (f)M.A. Malwitz, S.H. Lim, R.L. White-Morris, et al., J. Am. Chem. Soc. 134(2012) 10885-10893.
7. [7]
  K.C. Tang, M.J. Chang, T.Y. Lin, et al., J. Am. Chem. Soc. 133(2011) 17738-17745. doi: 10.1021/ja2062693
8. [8]
  (a) T. Mutai, H. Tomoda, T. Ohkawa, Y. Yabe, K. Araki, Angew. Chem. Int. Ed. 47(2008) 9522-9524;
  (b)R. Wei, P. Song, A. Tong, J. Phys. Chem. C 117(2013) 3467-3474.
9. [9]
  H. Liu, X. Cheng, H. Zhang, Y. Wang, S. Yamaguchi, Chem. Commun. 53(2017) 7832-7835. doi: 10.1039/C7CC03758A
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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

Four organic crystals displaying distinctively different emission colors based on an ESIPT-active organic molecule

References

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通讯作者: 陈斌, bchen63@163.com