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Progress in Chemistry 2023, Vol. 35 Issue (12): 1764-1782 DOI: 10.7536/PC230422 Previous Articles   Next Articles

• Review •

Preparation and Applications of Chiral Carbon Dots Prepared via Hydrothermal Carbonization Method

Jinyue Fan, Xiangxin Kong, Wei Li, Shouxin Liu*()   

  1. Key Laboratory of Bio-based Material Science & Technology, Northeast Forestry University,Harbin 150040,China
  • Received: Revised: Online: Published:
  • Contact: *e-mail:liushouxin@126.com
  • Supported by:
    National Natural Science Foundation of China(32371808); National Natural Science Foundation of China(31890773); National Natural Science Foundation of China(31971601)
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As an emerging carbon nanomaterial, chiral carbon dots (CCDs) have the unique photoelectric properties of carbon dots and chiral characteristics, which have good development prospects. The preparation of CCDs by hydrothermal carbonization includes a one-step method based on the chiral transfer strategy and a two-step method based on the chiral inheritance strategy, which exhibited the advantages of easy control of chiral structure, adjustable optical properties, environmental friendliness and excellent water solubility. It has good application effects in the fields of biomedicine, sensing, asymmetric catalysis, optoelectronic materials and composites, and is the most widely used preparation method at present. In this paper, the effects of experimental conditions (source types, hydrothermal conditions) on the chiral characteristics, physical chemical structure, optical properties and electrical properties of CCDs prepared by hydrothermal carbonization are reviewed. The applications of chiral carbon dots are summarized and their future developments are prospected.

Contents

1 Introduction

2 Preparation of chiral carbon dots by hydrothermal carbonization

2.1 One-step method based on chiral transfer strategy

2.2 Two-step method based on chiral inheritance strategy

3 Effect of preparation factors on the properties of chiral carbon dots

3.1 Effect of carbon source

3.2 Effect of chiral ligands

3.3 Effect of other source

3.4 Effect of hydrothermal carbonization temperature

3.5 Effect of hydrothermal carbonization time

4 Structural characteristics of chiral carbon dots prepared by hydrothermal carbonization

4.1 Chiral characteristics

4.2 Physical structure

4.3 Chemical structure

4.4 Optical property

4.5 Electrical property

5 Applications of chiral carbon dots prepared by hydrothermal carbonization

5.1 Biomedical

5.2 Sensing

5.3 Asymmetric catalysis

5.4 Photoelectric material

5.5 Composites

6 Conclusion and outlook

Key words: chirality, carbon dots, hydrothermal carbonization, optical characteristics, biomedical, sensing, composites
Fig. 1 (A) Preparation of CCDs via one-step method of citric acid and L-/D-cysteine[46]; (B) Synthesis of CCDs using L-/D-Cysteine as chiral source and carbon source[29];(C)Synthesis of CCDs using L-/D-Tryptophon as chiral source and carbon source[31];(D) Schematic of the preparation procedure for full-color CPL CCDs-CsPbX3[59]
Table 1 One-step method based on chiral transfer strategy
Method Chiral source Carbon source Other source T(℃) t(h) EM(nm) ref
One-step method L-/D-glutamine Citric acid — 140 16 450 45
L-/D-cysteine Citric acid — 180 1 — 46
L-/D-cysteine — NaOH 120 16 460 29
L-aspartic acid Citric acid NaOH 200 4 420 30
L-cysteine Citric acid — 160 6 453 47
L-cysteine
L-glutathione
L-phenylglycine
L-tryptophan		 Citric acid+
ethylenediamine		 — 190 8 450 48
L-/D-tryptophan — NaOH 120 16 476 31,67
L-/D-tryptophan o-Phenylenediamine HCl+Ethanol
-H2SO4		 160 7 441
546
604		 32
L-/D-cysteine Urea — 180 1 450 49
L-/D-glutamic acid Citric acid — 180 4 454/418 50
D-proline Citric acid — 180 2 420 51
L-/D-alanine Citric acid — 160 4 400 66
L-cysteine m-Phenylenediamine — 200 2 510 52
L-ascorbic acid
L-cysteine+L-ascorbic acid		 Ethylenediamine
Ethylenediamine		 — 100
140		 2
4		 484
420		 67
L-cysteine Neutral red Ethanol 140 8 601/604 75
L-/D-tryptophan OTD H2SO4 160 8 — 69
L-/D-glutamic acid Citric acid NaOH 180 10 407 34
D-(-)-fructose Vine teas NADES 160 3 445 35
L-/D-cysteine Citric acid — 180 1.5 442 54
L-glutathione Ethylenediamine — 200 6 390 57
L-/D-lysine Jeffamine® ED-900 Ethylene glycol 170 3 400~600 37
L-/D-lysine Jeffamine® ED-900 Ethylene glycol 170 2 400~600 38
L-/D-cysteine — NaOH 60 24 510 39
L-/D-cysteine — — 80 48 — 55
L-/D-glutamic Citric acid Polyethyleneimine 160 1 450 41
L-/D-cysteine — NaOH 120 16 460 42
L-/D-cysteine Citric acid — 160 6 445 58
L-/D-serine — — 140 8 475 59
L-/D-cysteine
L-/D-glutathione
L-/D-threonine		 Citric acid — 180 1.5 432
425
430		 60
L-tyrosine o-phenylenediamine H2SO4 160 7 627 43
Fig. 2 Synthesis of CCD by two-step method[9]
Table 2 Two-step method based on chiral inheritance strategy
Method Chiral source Carbon source Other source T(℃) t(h) EM(nm) ref
Two-step method L-/D-cysteine Citric acid+ethylenediamine — 160 4 424 9
L-/D-cysteine Urea — 180 1 450 49
L-/D-cysteine Citric acid+Urea DMF 180 6 625 33,68
L-/D-arginine/L-lysine Citric acid+Urea DMF 160 6 >600 44
L-/D-cysteine Cane molasses — 160+120 24+2 400~440 61
Fig. 3 (A) (i) Preparation of carbon dots; (ii) synthesis of CCDs by two-step method; (iii) synthesis of CCDs by one-step method[49]. (B) Particle size distribution of the products[49]
Fig. 4 (A) CCDs synthesized from vine tea and NADES as raw materials[37] (B) CCDs were synthesized by hydrothermal carbonization of citric acid and ethylenediamine with four chiral precursors of (ⅰ) L-cysteine, (ⅱ) L-glutathione, (ⅲ) L-phenylglycine, and (ⅳ) tryptophan[49]
Fig. 5 (A~C) TEM image and size distribution histograms of CCDs prepared by L-/D-cysteine[29,40,42]. (D) The preparation procedure for multicolor-emitting chiral carbon dots[32]. (Reprinted with permission from ref 42; Copyright (2023) American Chemical Society)
Fig. 6 (A) CD and glum spectra of CCDs prepared at different reaction temperatures[67]. (B) CD spectra of CCDs were prepared at different reaction times[51]. (C,D) glum spectra of CCDs prepared at different reaction temperatures and times[60]
Fig. 7 Circular dichroism of (A) L-/D-glutamic acid raw material and glutamic acid based CCDs[50]. (B) Mechanism of L-CDs synthesis from L-Tryptophan[31]
Fig. 8 (A) HRTEM image of CCDs prepared by L-/D-cysteine[29]. (B) FTIR spectra of CCDs samples prepared by different methods[49]
Fig. 9 (A) Laser confocal images of HeLa cells labelled with L-CDs[75]. Morphology of PrP (106~126) (A1) without CCDs, in the presence of (B2) L-CDs and (B3) D-CDs[37]
Fig. 10 (ⅰ) CCDs and (ⅱ) chiral nanovaccines and (ⅲ) application process[34].Reprinted with permission from ref 34; Copyright 2022 American Chemical Society
Fig. 11 Digital photograph of mung bean plants after 5 days of incubation with different concentrations of CCD[54]
Fig. 12 (A) Color change of CCDs aqueous solution and CCDs embedded in nanopaper after adding L-/D-Lys of different concentrations under UV irradiation[9]. (B) Fabricating CCDs-based nanoprobes for assaying Sn2+ and L-Lys in On-Off-On mode[30]. (C) Chiral recognition method based on CCDs towards isoleucine enantiomers[47]
Fig. 13 (A) Synthesis process of L-/D-Glu-CDs and the response of L-/D-Glu-CDs@Cu2+ to GAT in fluorescence spectra and CD spectra[50]. (B) Synthesis of CCDs and identification of lysine enantiomers[35]
Fig. 14 Detection of arginine by CCDs fluorescence probe[57]
Fig. 15 (A)Scheme showing the fabrication of luminescent chiral nematic CDs/CNC films[53]. (B) The photograph of CPL film under white and ultraviolet light[56]
Fig. 16 (A) Photos of the as-prepared L-CDs-CsPbX3 in UV light (upper) and daylight (bottom), respectively[59]. (B) CCDs induce porphyrin formation chiral materials[40]
Fig. 17 (A) CCDs encapsulated in ZIF-8 nanoparticles for turn-on recognition of chiral folic acid and nitrofurazone[58]. (B) Chiral dual-emission composite material fluorescein/CCDs@ZIF-8 for highly sensitive discrimination of phenylenediamine (PD) isomers and their oxidized product (2-MIM: 2-methylimidazole)[82]
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