Citation: Wenyan Ma, Bolun Wang, Yonggang Yang, Jiyang Li. Photoluminescent chiral carbon dots derived from glutamine[J]. Chinese Chemical Letters, ;2021, 32(12): 3916-3920. doi: 10.1016/j.cclet.2021.05.021 shu

Photoluminescent chiral carbon dots derived from glutamine

Wenyan Ma ^a ,
Bolun Wang ^a ,
Yonggang Yang ^b ,
Jiyang Li ^{a, *,}

a.
State Key Laboratory of Inorganic Synthesis and Preparative Chemistry, College of Chemistry, Jilin University, Changchun 130012, China
b.
Jiangsu Key Laboratory of Advanced Functional Polymer Design and Application Department of Polymer Science and Engineering, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, China

lijiyang@jlu.edu.cn

Received Date: 23 February 2021
Revised Date: 10 May 2021
Accepted Date: 13 May 2021
Available Online: 24 May 2021

Figures(5)

The integration of luminescence and chirality in carbon dots (CDs) encourages candidates to explore novel functions and applications of CDs, however, the preparation of chiral CDs is very limited. Herein, we report a hydrothermal method to fabricate chiral CDs by utilizing amino acid enantiomers as the precursors. LGln-CDs or DGln-CDs with uniform size of 3–4 nm show excitation-dependent blue fluorescence in solutions. Circular dichroism measurement confirms the opposite optical rotation of chiral CDs in the region from 200 nm to 300 nm, and the signals can be regulated by concentrations of CDs solution. Time-dependent density functional calculation reveals that polypeptides may exist on the surface of CDs due to the polycondensation of L/DGln at high temperature, and the optical activity of CDs originates from the stacking of neighboring carbonyl groups. The facile synthetic methodology proposed will provide potential opportunities for the preparation and application of chiral and chiroptical CDs-based materials.
- Chirality,
- Carbon dots,
- Photoluminescence,
- Circular dichroism,
- Sensors
1. [1]
  X.Y. Xu, R. Ray, Y.L. Gu, et al., J. Am. Chem. Soc.126 (2004) 12736–12737 doi: 10.1021/ja040082h
2. [2]
  F. Li, D.Y. Yang, H.P. Xu, Chem. Eur J. 25 (2019) 1165–1176 doi: 10.1002/chem.201802793
3. [3]
  W.D. Li, Y. Liu, B.Y. Wang, et al., Chin. Chem. Lett. 30 (2019) 2323–2327 doi: 10.1016/j.cclet.2019.06.040
4. [4]
  B.Y. Wang, J.K. Yu, L. Sui, et al., Adv. Sci. (2020) 2001453
5. [5]
  L. Xiao, H.D. Sun, Nanoscale Horiz. 3 (2018) 565–597 doi: 10.1039/c8nh00106e
6. [6]
  J.J. Du, N. Xu, J.L. Fan, W. Sun, X.J. Peng, Small15 (2019) 1805087 doi: 10.1002/smll.201805087
7. [7]
  B.L. Wang, Y. Mu, H.Y. Zhang, et al., ACS Cent. Sci. 5 (2019) 349–356 doi: 10.1021/acscentsci.8b00844
8. [8]
  B.L. Wang, Y. Yu, H.Y. Zhang, et al., Angew. Chem. Int. Ed. 58 (2019) 18443–18448 doi: 10.1002/anie.201911035
9. [9]
  H.Q. Song, Y.H. Li, L. Shang, et al., Nano Energy72 (2020) 104730 doi: 10.1016/j.nanoen.2020.104730
10. [10]
  Y.F. Wang, B.L. Wang, H.Z. Shi, et al., Inorg. Chem. Front. 5 (2018) 2739–2745 doi: 10.1039/c8qi00637g
11. [11]
  Y.F. Wang, X.S. Liu, M.K. Wang, et al., Sens. Actuators B329 (2021) 129115 doi: 10.1016/j.snb.2020.129115
12. [12]
  J. Tang, B. Kong, H. Wu, et al., Adv. Mater. 25 (2013) 6569–6574 doi: 10.1002/adma.201303124
13. [13]
  W.Q. Li, Z.G. Wang, S.J. Hao, et al., Nanoscale 10 (2018) 3744–3752 doi: 10.1039/C7NR08816G
14. [14]
  H. Wang, C.Q. Liu, Z. Liu, J.S. Ren, X.G. Qu, Small14 (2018) 1703710 doi: 10.1002/smll.201703710
15. [15]
  Y.Z. Han, H. Huang, H.C. Zhang, et al., ACS Catal. 4 (2014) 781–787 doi: 10.1021/cs401118x
16. [16]
  W.D. Li, Y.X. Zhao, Y. Liu, et al., Angew. Chem. Int. Ed. 60 (2021) 3290–3298 doi: 10.1002/anie.202013985
17. [17]
  Y.L. Zhang, Q. Ran, Q. Wang, et al., Adv. Mater. 31 (2019) 1902368 doi: 10.1002/adma.201902368
18. [18]
  J.L. Wang, F. Zhang, Y.L. Wang, Y.Z. Yang, X.G. Liu, Carbon 126 (2018) 426–436 doi: 10.1016/j.carbon.2017.10.041
19. [19]
  F.L. Yuan, Z.B. Wang, X.H. Li, et al., Adv. Mater. 29 (2017) 1604436 doi: 10.1002/adma.201604436
20. [20]
  C. Sun, Y. Zhang, K. Sun, et al., Nanoscale 7 (2015) 12045–12050 doi: 10.1039/C5NR03014E
21. [21]
  G.E. LeCroy, S.T. Yang, F. Yang, et al., Coord. Chem. Rev. 320–321 (2016) 66–81
22. [22]
  K. Hola, Y. Zhang, Y. Wang, et al., Nano Today9 (2014) 590–603 doi: 10.1016/j.nantod.2014.09.004
23. [23]
  S. Chung, R.A. Revia, M.Q. Zhang, Adv. Mater. (2019) https://doi.org/10.1002adma.201904362
24. [24]
  Z.L. Peng, X. Han, S.H. Li, et al., Coord. Chem. Rev. 343 (2017) 256–277 doi: 10.1016/j.ccr.2017.06.001
25. [25]
  J. Zhang, S.H. Yu, Mater. Today19 (2016) 382–393 doi: 10.1016/j.mattod.2015.11.008
26. [26]
  S.J. Zhu, Q.N. Meng, L. Wang, et al., Angew. Chem. Int. Ed. 125 (2013) 4045–4049 doi: 10.1002/ange.201300519
27. [27]
  C.L. Hao, L.G. Xu, H. Kuang, C.L. Xu, Adv. Mater. 32 (2019) 1802075
28. [28]
  J. Crassous, Chem. Soc. Rev. 38 (2009) 830–845 doi: 10.1039/b806203j
29. [29]
  T.G. Schaaff, G. Knight, M.N. Shafigullin, R.F. Borkman, R.L. Whetten, J. Phys. Chem. B102 (1998) 10643–10646 doi: 10.1021/jp9830528
30. [30]
  C. Gautier, T. Bürgi, ChemPhysChem10 (2009) 483–492 doi: 10.1002/cphc.200800709
31. [31]
  J. Kumar, K.G. Thomas, L.M. Liz-Marzan, Chem. Commun., 52 (2016) 12555–12569 doi: 10.1039/C6CC05613J
32. [32]
  V. Cherpak, V.F. Korolovych, R. Geryak, et al., Nano Lett. 18 (2018) 6770–6777 doi: 10.1021/acs.nanolett.8b02522
33. [33]
  H.Z. Zheng, W.R. Li, W. Li, et al., Adv. Mater. 30 (2018) 1705948 doi: 10.1002/adma.201705948
34. [34]
  L. Ðorđević, F. Arcudi, A. D'Urso, et al., Nat. Commun. 9 (2018) 3442 doi: 10.1038/s41467-018-05561-2
35. [35]
  A. Querejeta-Fernández, G. Chauve, M. Methot, J. Bouchard, E. Kumacheva, J. Am. Chem. Soc. 136 (2014) 4788–4793 doi: 10.1021/ja501642p
36. [36]
  M.L. Zhang, H.B. Wang, B. Wang, et al., Small15 (2019) 1901512 doi: 10.1002/smll.201901512
37. [37]
  L.L. Hu, Y. Sun, Y.J. Zhou, et al., Inorg. Chem. Front. 4 (2017) 946–953 doi: 10.1039/C7QI00118E
38. [38]
  R. Malishev, E. Arad, S.K. Bhunia, et al., Chem. Commun. 54 (2018) 7762–7765 doi: 10.1039/C8CC03235A
39. [39]
  L.L. Hu, H. Li, C.A. Liu, et al., Nanoscale 10 (2018) 2333–2340 doi: 10.1039/C7NR08335A
40. [40]
  Y.L. Zhang, L.L. Hu, Y. Sun, et al., RSC Adv. 6 (2016) 59956–59960 doi: 10.1039/C6RA12420H
41. [41]
  T.N. Pham-Truong, T. Petenzi, C. Ranjan, H. Randriamahazaka, J. Ghilane, Carbon 130 (2018) 544–552 doi: 10.1016/j.carbon.2018.01.070
42. [42]
  Y. Ru, L. Ai, T.T. Jia, et al., Nano Today34 (2020) 100953 doi: 10.1016/j.nantod.2020.100953
43. [43]
  S. Sahu, B. Behera, T.K. Maiti, S. Mohapatra, Chem. Commun. 48 (2012) 8835–8837 doi: 10.1039/c2cc33796g
44. [44]
  X.X. Shi, Y.L. Hu, H.M. Meng, et al., Sens. Actuators B. 306 (2020) 127582 doi: 10.1016/j.snb.2019.127582
45. [45]
  X. Geng, Y.Q. Sun, Z.H. Li, et al., Small15 (2019) 1901517 doi: 10.1002/smll.201901517
46. [46]
  M.L. Zhang, L.L. Hu, H.B. Wang, et al., Nanoscale 10 (2018) 12734–12742 doi: 10.1039/C8NR01644E
47. [47]
  Y.Y. Wei, L. Chen, J.L. Wang, et al., RSC Adv. 9 (2019) 3208–3214 doi: 10.1039/c8ra09649j
48. [48]
  H. Ding, S.B. Yu, J.S. Wei, H.M. Xiong, ACS Nano. 10 (2016) 484–491 doi: 10.1021/acsnano.5b05406
49. [49]
  X.R. Liu, S.X. Zhang, H. Xu, et al., ACS Appl. Mater. Interfaces12 (2020) 47245–47255 doi: 10.1021/acsami.0c12750
50. [50]
  S.J. Zhu, Y.B. Song, J.R. Shao, X.H. Zhao, B. Yang, Angew. Chem. Int. Ed. 54 (2015) 14626–14637 doi: 10.1002/anie.201504951
51. [51]
  B.L. Wang, Y. Mu, C.H. Zhang, J.Y. Li, Sens. Actuators B253 (2017) 911–917 doi: 10.1016/j.snb.2017.07.046
52. [52]
  Z. Guo, Z.Q. Zhang, W. Zhang, et al., ACS Appl. Mater. Interfaces6 (2014) 20700–20708 doi: 10.1021/am5071078
53. [53]
  M.J. Frisch, G.W. Trucks, H.B. Schlegel, et al., Gaussian09, Revision D. 01 Gaussian, 2013
54. [54]
  L.L. Zhou, D.X. Zheng, B. Wu, Y.Q. Zhu, L.L. Zhu, ACS Appl. Nano Mater. 3 (2020) 946–952 doi: 10.1021/acsanm.9b01677
55. [55]
  K.G. Qu, J.S. Wang, J.S. Ren, X.G. Qu, Chem. Eur. J. 19 (2013) 7243–7249 doi: 10.1002/chem.201300042
56. [56]
  Y. Song, C.Z. Zhu, J.H. Song, et al., ACS Appl. Mater. Interfaces9 (2017) 7399–7405 doi: 10.1021/acsami.6b13954
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