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化学进展 2023, Vol. 35 Issue (12): 1764-1782 DOI: 10.7536/PC230422 前一篇   后一篇

• 综述 •

水热炭化制备手性碳点及其应用

范金玥, 孔祥鑫, 李伟, 刘守新*()   

  1. 生物质材料科学与技术教育部重点实验室 东北林业大学 哈尔滨 150040
  • 收稿日期:2023-04-24 修回日期:2023-08-23 出版日期:2023-12-24 发布日期:2023-09-01
  • 基金资助:
    国家自然科学基金项目(32371808); 国家自然科学基金项目(31890773); 国家自然科学基金项目(31971601)
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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:2023-04-24 Revised:2023-08-23 Online:2023-12-24 Published:2023-09-01
  • 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)

手性碳点(Chiral carbon dots, CCDs) 具有碳点独特的光电性质同时兼具手性特征,是一种具有较好发展前景的新兴纳米炭材料。水热炭化法制备CCDs包括基于手性传递策略的一步法和手性继承策略两步法,具有手性结构容易控制、光学性质可调、环境友好、水溶性优异的优点,在生物医学、传感、不对称催化、光电材料及复合材料领域中具有较好的应用效果,是目前应用最广泛的制备方法。本文综述了水热炭化制备CCDs的实验条件(原料种类、水热条件)对其手性特征、物理化学结构、光学性质和电学性质的影响,对CCDs应用进行了概述,对其未来发展进行了展望。

关键词： 手性, 碳点, 水热炭化, 光学特征, 生物医学, 传感, 复合材料

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
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图1 (A) 以柠檬酸和L-/D-半胱氨酸一步法制备CCDs[46];(B) 以L-/D-半胱氨酸为手性源和碳源合成CCDs[29];(C)以L-/D-色氨酸为手性源和碳源合成CCDs[31];(D) 全彩色CPL发射的CCDs-CsPbX3的制备[59]
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]
表1 基于手性传递策略的一步法合成CCDs
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
图2 两步法合成CCD[9]
Fig. 2 Synthesis of CCD by two-step method[9]
表2 基于手性继承策略的两步法合成CCDs
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
图3 (A) (ⅰ) 碳点的制备; (ⅱ) 两步法合成CCDs; (ⅲ) 一步法合成CCDs[49]; (B) 产物的粒径分布[49]
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]
图4 (A) 以藤茶和NADES为原料合成CCDs[37];(B) 以柠檬酸和乙二胺与(ⅰ) L-半胱氨酸,(ⅱ) L-谷胱甘肽,(ⅲ) L-苯基甘氨酸,(ⅳ) 色氨酸四种手性前驱体为原料水热炭化合成CCDs[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]
图5 (A~C) 以L-/D-半胱氨酸为原料合成CCDs的TEM图和尺寸分布图[29,40,42];(D) 多色CCDs的制备[32]
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)
图6 (A) 不同温度下制备CCDs的CD光谱和glum光谱[67]; (B) 不同反应时间制备CCDs的CD光谱[51]; (C,D) 不同反应温度和时间制备CCDs的glum光谱[60]
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]
图7 (A) L-/D-谷氨酸原料和谷氨酸基CCDs的圆二色谱[50]. (B) L-色氨酸合成L-CDs机理[31]
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]
图8 (A) 以L-/D-半胱氨酸为原料合成CCDs的HRTEM图[29];(B) 不同方法制备的CCDs的FTIR图[49]
Fig. 8 (A) HRTEM image of CCDs prepared by L-/D-cysteine[29]. (B) FTIR spectra of CCDs samples prepared by different methods[49]
图9 (A) 用L-CDs标记的HeLa细胞的激光共聚焦图像[75]; (B1) 没有CCDs;(B2) 有L-CDs存在的和(B3) 有D-CDs存在下PrP(106~126)的形态[37]
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]
图10 (ⅰ) CCDs和(ⅱ) 手性纳米疫苗的制备以及(ⅲ) 应用过程[34]
Fig. 10 (ⅰ) CCDs and (ⅱ) chiral nanovaccines and (ⅲ) application process[34].Reprinted with permission from ref 34; Copyright 2022 American Chemical Society
图11 不同浓度CCDs培养5天后绿豆植物的数码照片[54]
Fig. 11 Digital photograph of mung bean plants after 5 days of incubation with different concentrations of CCD[54]
图12 (A) 紫外光照射下加入不同浓度的L-/D-Lys后CCDs水溶液和将CCDs嵌入纳米纸的颜色变化[9]; (B) 基于CCDs在On-Off-On模式下测定Sn2+和L-Lys纳米探针的制备[30]; (C) CCDs对异亮氨酸对映体的识别[47]
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]
图13 (A) L-/D-谷氨酸基CCDs的合成过程以及L-/D-Glu-CDs@Cu2+对GAT响应的荧光光谱和CD光谱[50]; (B) CCDs的合成方法与对赖氨酸对映体的识别[35]
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]
图14 CCDs荧光探针检测精氨酸[57]
Fig. 14 Detection of arginine by CCDs fluorescence probe[57]
图15 (A) 发光手性向列相CDs/CNC薄膜的制备[53];(B) CPL膜在白光和紫外光照射下的照片[56]
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]
图16 (A) 制备好的L-CDs-CsPbX3在紫外光下(上)和日光下(下)的照片[59];(B) CCDs诱导卟啉形成手性材料[40]
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]
图17 (A) 将CCDs封装在ZIF-8纳米颗粒中用于识别叶酸和硝基呋喃酮[58];(B) 手性双发射复合材料荧光素/CCDs@ZIF-8用于苯二胺(PD)异构体及其氧化产物的高灵敏度鉴别 (2-MIM: 2-甲基咪唑)[82]
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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摘要

水热炭化制备手性碳点及其应用