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: 11 May 2020
Available Online: 15 May 2020

Figures(4)

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]
  Qian Ren , Xue Dai , Ran Cen , Yang Luo , Mingyang Li , Ziyun Zhang , Qinghong Bai , Zhu Tao , Xin Xiao . A cucurbit[8]uril-based supramolecular phosphorescent assembly: Cell imaging and sensing of amino acids in aqueous solution. Chinese Chemical Letters, 2024, 35(12): 110022-. doi: 10.1016/j.cclet.2024.110022
2. [2]
  Dian-Xue Ma , Yu-Wu Zhong . Achieving highly-efficient room-temperature phosphorescence with a nylon matrix. Chinese Journal of Structural Chemistry, 2024, 43(9): 100391-100391. doi: 10.1016/j.cjsc.2024.100391
3. [3]
  Zeyin Chen , Jiaju Shi , Yusheng Zhou , Peng Zhang , Guodong Liang . Polymer microparticles with ultralong room-temperature phosphorescence for visual and quantitative detection of oxygen through phosphorescence image and lifetime analysis. Chinese Chemical Letters, 2025, 36(5): 110629-. doi: 10.1016/j.cclet.2024.110629
4. [4]
  Kun Zhang , Ni Dan , Dan-Dan Ren , Ruo-Yu Zhang , Xiaoyan Lu , Ya-Pan Wu , Li-Lei Zhang , Hong-Ru Fu , Dong-Sheng Li . A small D-A molecule with highly heat-resisting room temperature phosphorescence for white emission and anti-counterfeiting. Chinese Journal of Structural Chemistry, 2024, 43(3): 100244-100244. doi: 10.1016/j.cjsc.2024.100244
5. [5]
  Jiayin Zhou , Depeng Liu , Longqiang Li , Min Qi , Guangqiang Yin , Tao Chen . Responsive organic room-temperature phosphorescence materials for spatial-time-resolved anti-counterfeiting. Chinese Chemical Letters, 2024, 35(11): 109929-. doi: 10.1016/j.cclet.2024.109929
6. [6]
  Jianmei Guo , Yupeng Zhao , Lei Ma , Yongtao Wang . Ultra-long room temperature phosphorescence, intrinsic mechanisms and application based on host-guest doping systems. Chinese Journal of Structural Chemistry, 2024, 43(9): 100335-100335. doi: 10.1016/j.cjsc.2024.100335
7. [7]
  Hong Yao , Feixiang Yang , Jianpeng Hu , Wenyu Cao , Shuning Qin , Tai-Bao Wei , Bingbing Shi , Qi Lin . Ultralong room temperature phosphorescence and broad color-tunability persistent luminescence via new strategy. Chinese Chemical Letters, 2025, 36(6): 110375-. doi: 10.1016/j.cclet.2024.110375
8. [8]
  Chunqing Ou , Meijia Xiao , Xinyue Zheng , Xianzhou Huang , Suleixin Yang , Yingying Leng , Xiaowei Liu , Xiuqi Liang , Linjiang Song , Yanjie You , Shaohua Yao , Changyang Gong . Programmable double-unlock nanocomplex self-supplies phenylalanine ammonia-lyase for precise phenylalanine deprivation of tumors. Chinese Chemical Letters, 2024, 35(8): 109275-. doi: 10.1016/j.cclet.2023.109275
9. [9]
  Shaofeng Gong , Zi-Wei Deng , Chao Wu , Wei-Min He . Stabilized carbon radical-mediated three-component functionalization of amino acid/peptide derivatives. Chinese Chemical Letters, 2025, 36(5): 110936-. doi: 10.1016/j.cclet.2025.110936
10. [10]
  Liangyu Zhang , Lei Lei , Zhuangzhuang Zhao , Guizhi Yang , Kaitao Wang , Liying Wang , Ningxin Zhang , Yanjia Ai , Xinqing Ma , Guannan Liu , Meng Zhao , Jun Wu , Dongjun Lin , Chun Chen . Enhanced venetoclax delivery using l-phenylalanine nanocarriers in acute myeloid leukemia treatment. Chinese Chemical Letters, 2025, 36(6): 110316-. doi: 10.1016/j.cclet.2024.110316
11. [11]
  Yiyue Ding , Qiuxiang Zhang , Lei Zhang , Qilu Yao , Gang Feng , Zhang-Hui Lu . Exceptional activity of amino-modified rGO-immobilized PdAu nanoclusters for visible light-promoted dehydrogenation of formic acid. Chinese Chemical Letters, 2024, 35(7): 109593-. doi: 10.1016/j.cclet.2024.109593
12. [12]
  Shiqi Peng , Yongfang Rao , Tan Li , Yufei Zhang , Jun-ji Cao , Shuncheng Lee , Yu Huang . Regulating the electronic structure of Ir single atoms by ZrO₂ nanoparticles for enhanced catalytic oxidation of formaldehyde at room temperature. Chinese Chemical Letters, 2024, 35(7): 109219-. doi: 10.1016/j.cclet.2023.109219
13. [13]
  Shuai Zhu , Mingjie Chen , Haichao Shen , Hanming Ding , Wenbo Li , Junliang Zhang . Palladium/Xu-Phos-catalyzed enantioselective arylalkoxylation reaction of γ-hydroxyalkenes at room temperature. Chinese Chemical Letters, 2024, 35(11): 109879-. doi: 10.1016/j.cclet.2024.109879
14. [14]
  Qian Wang , Ting Gao , Xiwen Lu , Hangchao Wang , Minggui Xu , Longtao Ren , Zheng Chang , Wen Liu . Nanophase separated, grafted alternate copolymer styrene-maleic anhydride as an efficient room temperature solid state lithium ion conductor. Chinese Chemical Letters, 2024, 35(7): 108887-. doi: 10.1016/j.cclet.2023.108887
15. [15]
  Xin Li , Ling Zhang , Yunyan Fan , Shaojing Lin , Yong Lin , Yongsheng Ying , Meijiao Hu , Haiying Gao , Xianri Xu , Zhongbiao Xia , Xinchuan Lin , Junjie Lu , Xiang Han . Carbon interconnected microsized Si film toward high energy room temperature solid-state lithium-ion batteries. Chinese Chemical Letters, 2025, 36(2): 109776-. doi: 10.1016/j.cclet.2024.109776
16. [16]
  Sheng Zhao , Junjie Lu , Bifu Sheng , Siying Zhang , Hao Li , Jizhang Chen , Xiang Han . High-performance room temperature solid-state lithium battery enabled by PP-PVDF multilayer composite electrolyte. Chinese Chemical Letters, 2025, 36(6): 110008-. doi: 10.1016/j.cclet.2024.110008
17. [17]
  Tao Tang , Chen Li , Sipu Li , Zhong Qiu , Tianqi Yang , Beirong Ye , Shaojun Shi , Chunyang Wu , Feng Cao , Xinhui Xia , Minghua Chen , Xinqi Liang , Xinping He , Xin Liu , Yongqi Zhang . One-step constructing advanced N-doped carbon@metal nitride as ultra-stable electrocatalysts via urea plasma under room temperature. Chinese Chemical Letters, 2024, 35(11): 109887-. doi: 10.1016/j.cclet.2024.109887
18. [18]
  Yu-Yao Li , Xiao-Hui Li , Zhi-Xuan An , Yang Chu , Xiu-Li Wang . Room-temperature olefin epoxidation reaction by two 2D cobalt metal-organic complexes under O₂ atmosphere: Coordination and structural regulation. Chinese Chemical Letters, 2025, 36(4): 109716-. doi: 10.1016/j.cclet.2024.109716
19. [19]
  Lu Dai , Yuxin Ren , Shuang Li , Meidi Wang , Chentao Hu , Ya-Pan Wu , Guangtong Hai , Dong-Sheng Li . Room-temperature synthesis of Co(OH)₂/Mo₂TiC₂T_x hetero-nanosheets with interfacial coupling for enhanced oxygen evolution reaction. Chinese Chemical Letters, 2025, 36(4): 109774-. doi: 10.1016/j.cclet.2024.109774
20. [20]
  Siqi Sun , Cheng Zhao , Zhaohuan Zhang , Ding Wang , Xinru Yin , Jingting Han , Jinlei Wei , Yong Zhao , Yongheng Zhu . Highly selective QCM sensor based on functionalized hierarchical hollow TiO₂ nanospheres for detecting ppb-level 3-hydroxy-2-butanone biomarker at room temperature. Chinese Chemical Letters, 2025, 36(5): 109939-. doi: 10.1016/j.cclet.2024.109939

Get Citation

PDF

XML

Metrics

PDF Downloads(3)
Abstract views(891)
HTML views(37)

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