Citation: Zifei Wang, Teng Li, Bingbing Ding, Xiang Ma. Achieving room temperature phosphorescence from organic small molecules on amino acid skeleton[J]. Chinese Chemical Letters, ;2020, 31(11): 2929-2932. doi: 10.1016/j.cclet.2020.05.015 shu

Achieving room temperature phosphorescence from organic small molecules on amino acid skeleton

Key Laboratory for Advanced Materials and Feringa Nobel Prize Scientist Joint Research Center, School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai 200237, China

maxiang@ecust.edu.cn

Received Date: 11 April 2020
Revised Date: 9 May 2020
Accepted Date: 9 May 2020
Available Online: 15 November 2020

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Room temperature phosphorescence (RTP) generated by small molecules has attracted great attention due to their unique potentials for biosensor, bioimaging and security protection. While, the design of RTP materials is extremely challenging for organic small molecules in non-crystalline solid state. Herein, we report a new strategy for achieving non-crystalline organic small molecules with RTP emission by modifying different phosphors onto diphenylalanine or phenylalanine derivatives. Benefiting from the skeletal structure of the amino acid derivatives, there are intermolecular hydrogen bond formation and rigidification effect, thereby minimizing the intermolecular motions and enhancing their RTP performance
- Room temperature phosphorescence,
- Amino acid,
- Phenylalanine,
- Diphenylalanine
1. [1]
  B. Lu, S.Y. Liu, D.P. Yan, Chin. Chem. Lett. 30(2019) 1908-1922. doi: 10.1016/j.cclet.2019.09.012
2. [2]
  D.P. Yan, D.G. Evans, Mater. Horiz. 1(2014) 46-57. doi: 10.1039/C3MH00023K
3. [3]
  B. Zhou, D.P. Yan, Angew. Chem. Int. Ed. 58(2019) 15128-15135. doi: 10.1002/anie.201909760
4. [4]
  B. Zhou, D.P. Yan, Adv. Funct. Mater. 29(2019) 1807599. doi: 10.1002/adfm.201807599
5. [5]
  H. Wang, X. Lv, P. Wang, et al., Chin. Chem. Lett. 29(2018) 471-474. doi: 10.1016/j.cclet.2017.07.025
6. [6]
  X.Z. Song, D.D. Zhang, T.Y. Huang, et al., Sci. China Chem. 61(2018) 836-843. doi: 10.1007/s11426-018-9242-1
7. [7]
  B.W. Li, X.A. Song, X. Jiang, et al., Chin. Chem. Lett. 31(2020) 1188-1192. doi: 10.1016/j.cclet.2019.06.033
8. [8]
  Y. Liu, G. Zhan, Z.W. Liu, et al., Chin. Chem. Lett. 27(2016) 1231-1240. doi: 10.1016/j.cclet.2016.06.029
9. [9]
  B.I. Ipe, K. Yoosaf, K.G. Thomas, J. Am. Chem. Soc. 128(2006) 1907-1913. doi: 10.1021/ja054347j
10. [10]
  H.F. Shi, L. Zou, K.W. Huang, et al., ACS Appl. Mater. Interfaces 11(2019) 18103-18110. doi: 10.1021/acsami.9b01615
11. [11]
  J. Yang, X. Zhen, B. Wang, et al., Nat. Commun. 9(2018) 840. doi: 10.1038/s41467-018-03236-6
12. [12]
  R. Gao, X. Mei, D. Yan, et al., Nat. Commun. 9(2018) 2798. doi: 10.1038/s41467-018-05223-3
13. [13]
  N. Gan, H. Shi, Z. An, et al., Adv. Funct. Mater. 28(2018) 1802657. doi: 10.1002/adfm.201802657
14. [14]
  Q.X. Xiong, C. Xu, X. Ma, et al., Chin. Chem. Lett. 30(2019) 1387-1389. doi: 10.1016/j.cclet.2019.04.010
15. [15]
  T. Zhang, H. Chen, X. Ma, et al., Ind. Eng. Chem. Res. 56(2017) 3123-3128. doi: 10.1021/acs.iecr.7b00149
16. [16]
  Y.N. Zhang, J.F. Zhao, C.X. Zhu, et al., Chin. Chem. Lett. 30(2019) 1974-1978. doi: 10.1016/j.cclet.2019.09.005
17. [17]
  J.X. Wang, Y.G. Fang, C.X. Li, et al., Angew. Chem. Int. Ed. 59(2020) 10032-10036. doi: 10.1002/anie.202001141
18. [18]
  Z.H. He, W.B. Li, G. Chen, et al., Chin. Chem. Lett. 30(2019) 933-936. doi: 10.1016/j.cclet.2019.03.015
19. [19]
  X.Y. Fang, D.P. Yan, Sci. China Chem. 61(2018) 397-401. doi: 10.1007/s11426-017-9183-9
20. [20]
  Y.Y. Gong, G. Chen, Q. Peng, et al., Adv. Mater. 27(2015) 6195-6201. doi: 10.1002/adma.201502442
21. [21]
  M.S. Kwon, D. Lee, S. Seo, et al., Angew. Chem. Int. Ed. 53(2014) 11177-11181. doi: 10.1002/anie.201404490
22. [22]
  B. Zhou, D.P. Yan, Sci. China Chem. 62(2019) 291-292. doi: 10.1007/s11426-018-9389-7
23. [23]
  X. Wang, Y. Xu, X. Ma, et al., Ind. Eng. Chem. Res. 57(2018) 2866-2872. doi: 10.1021/acs.iecr.7b04759
24. [24]
  X. Ma, C. Xu, J. Wang, et al., Angew. Chem. Int. Ed. 57(2018) 10854-10858. doi: 10.1002/anie.201803947
25. [25]
  H. Chen, X.Y. Yao, X. Ma, et al., Adv. Opt. Mater. 4(2016) 1397-1401. doi: 10.1002/adom.201600427
26. [26]
  G.J. Qu, Y.P. Zhang, X. Ma, Chin. Chem. Lett. 30(2019) 1809-1814. doi: 10.1016/j.cclet.2019.07.042
27. [27]
  X. Ma, J. Wang, H. Tian, Acc. Chem. Res. 52(2019) 738-748. doi: 10.1021/acs.accounts.8b00620
28. [28]
  Y.F. Gong, H. Chen, X. Ma, et al., ChemPhysChem 17(2016) 1934-1938. doi: 10.1002/cphc.201500901
29. [29]
  X.F. Wang, W.J. Guo, H.Y. Xiao, et al., Adv. Funct. Mater. 30(2020) 1907282. doi: 10.1002/adfm.201907282
30. [30]
  W.J. Luo, Y.R. Zhang, Y.Y. Gong, et al., Chin. Chem. Lett. 29(2018) 1533-1536. doi: 10.1016/j.cclet.2018.08.001
31. [31]
  J.A. Li, J.H. Zhou, Z. Mao, et al., Angew. Chem. Int. Ed. 57(2018) 6449-6453. doi: 10.1002/anie.201800762
32. [32]
  X.H. Chen, W.J. Luo, H.L. Ma, et al., Sci. China Chem. 61(2018) 351-359. doi: 10.1007/s11426-017-9114-4
33. [33]
  Z.H. He, W.B. Li, G. Chen, et al., Chin. Chem. Lett. 30(2019) 933-936. doi: 10.1016/j.cclet.2019.03.015
34. [34]
  X. Wang, N. Gan, M.X. Gu, et al., Chin. Chem. Lett. 30(2019) 1935-1938. doi: 10.1016/j.cclet.2018.12.023
35. [35]
  N.A. Kukhta, R. Huang, A.S. Batsanov, et al., J. Phys. Chem. C 123(2019) 26536-26546. doi: 10.1021/acs.jpcc.9b08238
36. [36]
  R.J. Huang, J.S. Ward, N.A. Kukhta, et al., J. Mater. Chem. C 6(2018) 9238-9247. doi: 10.1039/C8TC02987C
37. [37]
  Q. Zhou, B.Y. Cao, C.X. Zhu, et al., Small 12(2016) 6586-6592. doi: 10.1002/smll.201601545
38. [38]
  Y.Y. Gong, Y.Q. Tan, J. Mei, et al., Sci. China Chem. 56(2013) 1178-1182. doi: 10.1007/s11426-013-4923-8
39. [39]
  A.H. Maki, J.A. Zuclich, Top. Curr. Chem. 54(1975) 115-163.
40. [40]
  C.X. Zhao, Y.H. Jin, X. Ma, et al., Chem. Commun. 55(2019) 5355-5358. doi: 10.1039/C9CC01594A
41. [41]
  D.F. Li, F.F. Lu, X. Ma, et al., J. Am. Chem. Soc. 140(2018) 1916-1923. doi: 10.1021/jacs.7b12800
42. [42]
  Y. Su, S.Z.F. Phua, Y.B. Li, et al., Sci. Adv. 4(2018) eaas9732. doi: 10.1126/sciadv.aas9732
43. [43]
  Q. Wang, M. Cheng, J.L. Jiang, et al., Chin. Chem. Lett. 28(2017) 793-797. doi: 10.1016/j.cclet.2017.02.008
44. [44]
  T. Zhang, C.Y. Wang, X. Ma, Ind. Eng. Chem. Res. 58(2019) 7778-7785. doi: 10.1021/acs.iecr.9b00910
45. [45]
  D.S. Wang, X. Wang, X. Ma, et al., Sci. China Chem. 62(2019) 430-433. doi: 10.1007/s11426-018-9383-2
1. [1]
  Mao Cai He , Yu Qi Li , Ya Xian Zhu , Yong Zhang . Metal nanoparticle-enhanced room temperature phosphorescence of diiodofluorescein on the filter paper substrate. Chinese Chemical Letters, 2010, 21(1): 109-112. doi: 10.1016/j.cclet.2009.08.008
2. [2]
  Li Xuan MU , Yu WANG , Zhao ZHANG , Wei Jun JIN . Room Temperature Phosphorescence pH Switch Based on Photo-induced Electron Transfer. Chinese Chemical Letters, 2004, 15(9): 1131-1134.
3. [3]
  Wei Zhang , Tian Tian Sun , Duo Mei , Jun Fei Wang , Ying Xia Li . Synthesis of protected (2S,4R)-2-amino-4-methyldecanoic acid, a proposed component of culicinins. Chinese Chemical Letters, 2008, 19(9): 1068-1070. doi: 10.1016/j.cclet.2008.06.027
4. [4]
  Yan Ming Liu , Zhuan Li Liu . Chemiluminescence determination of 20 amino acids and the mechanism study. Chinese Chemical Letters, 2010, 21(7): 856-859. doi: 10.1016/j.cclet.2010.01.025
5. [5]
  Meng-Yan Liu , Shi-Bin Hong , Wei Zhang , Wei Deng . Expedient copper-catalyzed borylation reactions using amino acids as ligands. Chinese Chemical Letters, 2015, 26(3): 373-376. doi: 10.1016/j.cclet.2014.12.004
6. [6]
  Ying Wu Lin , Chang Ming Nie , Li Fu Liao . Probing the weak interactions between amino acids and carbon monoxide. Chinese Chemical Letters, 2008, 19(1): 119-122. doi: 10.1016/j.cclet.2007.11.014
7. [7]
  Xin Rong QIN , Yu Li XIE , Qiao Ling ZHANG , Hui Bing LUO , Yu Yuan XIE . Synthesis of (2R, 4R)-2-N-tert-Butyloxycarbonyl Amino-4, 5-epoxido-valeric Acid Methyl Ester. Chinese Chemical Letters, 2002, 13(2): 111-112.
8. [8]
  Zhang Lu , Zhang Ying-Ming , Liu Guoxing , Liu Yu . Redox-responsive diphenylalanine aggregate mediated by cyclodextrin. Chinese Chemical Letters, 2019, 30(1): 120-122. doi: 10.1016/j.cclet.2018.04.028
9. [9]
  Li Zhou , Jiao Ning Tang , Bo Liu , Yi Guang Wu , Ai Lian Wang , Chuan Dong Liao . Novel hot-melting hyperbranched poly(ester-amine) bearing self-complementary quadruple hydrogen bonding units. Chinese Chemical Letters, 2008, 19(7): 871-876. doi: 10.1016/j.cclet.2008.05.015
10. [10]
  Ma Lifu , Ren Juan , Feng Ruxia , Zhang Kailin , Kong Xianglei . Structural characterizations of protonated homodimers of amino acids:Revealed by infrared multiple photon dissociation (IRMPD) spectroscopy and theoretical calculations. Chinese Chemical Letters, 2018, 29(9): 1333-1339. doi: 10.1016/j.cclet.2018.02.008
11. [11]
  Chun-Rui Wang , Yong-Yang Gong , Wang-Zhang Yuan , Yong-Ming Zhang . Crystallization-induced phosphorescence of pure organic luminogens. Chinese Chemical Letters, 2016, 27(8): 1184-1192. doi: 10.1016/j.cclet.2016.05.026
12. [12]
  Xiong Wei , Zhou Hantao , Zhang Chong , Lu Hua . An amino acid-based gelator for injectable and multi-responsive hydrogel. Chinese Chemical Letters, 2017, 28(11): 2125-2128. doi: 10.1016/j.cclet.2017.09.019
13. [13]
  Luo Weijian , Zhang Yiren , Gong Yongyang , Zhou Qing , Zhang Yongming , Yuan Wangzhang . Crystallization-induced phosphorescence, remarkable mechanochromism, and grinding enhanced emission of benzophenone-aromatic amine conjugates. Chinese Chemical Letters, 2018, 29(10): 1533-1536. doi: 10.1016/j.cclet.2018.08.001
14. [14]
  Liu Long , Wang Bo , Bi Cheng , He Gang , Chen Gong . Efficient preparation of β-hydroxy aspartic acid and its derivatives. Chinese Chemical Letters, 2018, 29(7): 1113-1115. doi: 10.1016/j.cclet.2018.05.012
15. [15]
  Li Yan , Miao Yan-Ming , Yang Mao-Qing , Wu Yu-Xia , Yan Gui-Qin . DNA detection based on Mn-doped ZnS quantum dots/methylene blue nanohybrids. Chinese Chemical Letters, 2016, 27(5): 773-778. doi: 10.1016/j.cclet.2016.01.006
16. [16]
  He Zihan , Li Wenbo , Chen Gan , Zhang Yongming , Yuan Wang-Zhang . Polymorphism dependent triplet-involved emissions of a pure organic luminogen. Chinese Chemical Letters, 2019, 30(4): 933-936. doi: 10.1016/j.cclet.2019.03.015
17. [17]
  , KHATOON Suraiya , NAQVI Andleeb Z. . Nonelectrolyte-Induced CP Variation of TX-114+TBAB System. Acta Physico-Chimica Sinica, 2008, 24(07): 1180-1184. doi: 10.1016/S1872-1508(08)60052-2
18. [18]
  PAN Hong , LIU Rang-Dong , WANG Wei-Wei , WANG Yan , YAN Chao . Preparation of A Novel Zwitterionic Hybrid Monolith Column with Incorporated Fumed Silica Nanoparticle and Its Application in Pressurized Capillary Electrochromatography. Chinese Journal of Analytical Chemistry, 2019, 47(4): 550-559. doi: 10.19756/j.issn.0253-3820.181722
19. [19]
  Yang Liu , Ge Zhan , Zhi-Wei Liu , Zu-Qiang Bian , Chun-Hui Huang . Room-temperature phosphorescence from purely organic materials. Chinese Chemical Letters, 2016, 27(8): 1231-1240. doi: 10.1016/j.cclet.2016.06.029
20. [20]
  Hai Rong ZHANG , Yan Sheng WEI , Wei Jun JIN , Chang Song LIU . Comparison of Four Deoxygenation Techniques for Cyclodextrin Induced Room Temperature Phosphorescence. Chinese Chemical Letters, 1997, 8(4): 339-342.

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