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化学进展 2022, Vol. 34 Issue (3): 499-518 DOI: 10.7536/PC210303 前一篇   后一篇

• 综述 •

碳点的高性能化和功能化改性:方法、特性与展望

李程浩1, 刘亚敏2, 卢彬1, 萨拉乌拉1, 任先艳1,*(), 孙亚平2,*()   

  1. 1 西南科技大学材料科学与工程学院 绵阳 621010
    2 克莱姆森大学化学学院 美国 克莱姆森 29634
  • 收稿日期:2021-03-03 修回日期:2021-04-16 出版日期:2021-07-29 发布日期:2021-07-29
  • 通讯作者: 任先艳, 孙亚平
  • 基金资助:
    西南科技大学博士启动基金(16ZX7139); 龙山人才项目(18LZX675)
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Toward High-Performance and Functionalized Carbon Dots: Strategies, Features, and Prospects

Chenghao Li1, Yamin Liu2, Bin Lu1, Ulla Sana1, Xianyan Ren1(), Yaping Sun2()   

  1. 1 School of Materials Science and Engineering, Southwest University of Science and Technology,Mianyang 621010, China
    2 Department of Chemistry, Clemson University, South Carolina 29634, USA
  • Received:2021-03-03 Revised:2021-04-16 Online:2021-07-29 Published:2021-07-29
  • Contact: Xianyan Ren, Yaping Sun
  • Supported by:
    Southwest University of Science and Technology of the Startup Foundation for Doctors(16ZX7139); Longshan Talent Program(18LZX675)

碳点作为一种新型碳纳米材料,由于其出色的光学性能、低毒性、良好的生物相容性和易修饰性而被广泛应用于各个领域。为了满足不同领域的需求,几种用以调控碳点光学性能的方法已被提出,例如杂原子掺杂、半导体量子点掺杂、聚合物钝化和改性以及主-客体构建。其中,杂原子掺杂是通过单原子或多原子引入电子给体或受体改变其相邻碳原子的电子密度来增加荧光强度;半导体量子点也可与碳点进行复合提升电子分离效率而起到荧光增强的效果;就聚合物改性而言,聚合物不仅可以对碳点表面实施钝化和功能化,而且其固态(或固化)薄膜可以提供紧密的空间促进碳点表面的辐射跃迁起到荧光增强的效果。此外,由碳点-染料和多孔材料-碳点构成的两种主要的主-客体结构中,前者不仅对碳点的荧光发射强度有着促进的作用,更使得碳点具备了显著的红/近红外荧光发射性能,后者对固态发光碳点不仅提供了可能性和设计的灵活性,且为打开碳点新的应用领域提供了机会。本文将围绕四种碳点功能化的方法逐步展开讨论,并介绍相应碳点的光学性能、发光机理和潜在应用;论述功能化碳点的研究现状,并展望功能化碳点的研究方向。

关键词： 碳点, 杂原子, 半导体量子点, 聚合物, 主-客体结构, 红光/近红外光发射

Carbon dots (CDots) emerging as a nova in carbon nanomaterials are applied in various fields due to their unique optical property, low toxicity, high biocompatibility, and designable flexibility. Several strategies for controlling the optical properties of CDots have been proposed to meet demands, including heteroatom doping, semiconductor quantum dot doping, polymer passivation and modification, and host-guest constructing. Electron donors or electron acceptors are introduced by doping a single heteroatom or multiple heteroatoms to affect the electron density of neighboring carbon atoms, hence enhancing the fluorescence emission intensity. Semiconductor quantum dots can also form composites with CDots to improve the electron hole separation efficiency, thus enhancing fluorescence. In terms of polymer modification, the polymer can passivate and functionalize the CDots' surface, and (cured) polymer film can provide tight spaces to promote the radiation transition on the surface of CDots to enhance the fluorescence. Furthermore, dye-CDots and porous material-CDots represent the main host-guest structures. The former shows positive effects on the fluorescence emission of CDots, especially performing better in red/near-infrared emission. The latter is highly designable and contributes to solid-state fluorescence, paving the way for advanced applications. This review elucidates four types of functionalized CDots and summarizes their optical properties, photoluminescence mechanisms, and potential applications. Finally, the development and current situation of functionalized CDots are discussed, and the future research direction of functionalized CDots has also been prospected.

Contents

1 Introduction

2 Heteroatom-doped carbon dots

2.1 N-doped carbon dots

2.2 Other donor atom-doped carbon dots

2.3 B-doped carbon dots

2.4 Lanthanide atom-doped carbon dots

2.5 Multiple atom-codoped carbon dots

3 Semiconductor quantum dot-doped carbon dots and their composites

4 Polymer functionalized carbon dots and their composites

4.1 Polymer as a surface layer of carbon dots for fluorescence enhancement

4.2 Polymer as a matrix in carbon dot-containing composites

4.3 Polymer as a precursor of carbon dots

5 Host-guest carbon dots

5.1 Host-guest structure composed of carbon dots and dyes

5.2 Host-guest structure composed of carbon dots and porous materials

6 Summary and outlook

Key words: carbon dots, heteroatom, semiconductor quantum dots, polymer, host-guest structure, red/near-infrared emission
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表1 部分已报到N-CDots的前驱体,结构和荧光性能
Table 1 The precursor, structure, and fluorescence performances of some reported N-CDots
Precursor N/C ratio/% N-related bond Average
diameter/nm		 QY/% λem/nm
Carbon source Nitrogen source
Glucose Ammonia 8.3 Pyridine, Pyrrole,Graphitic N 3.7 11.3(λex: 375 nm) 570[25]
Folic acid 10.5 Pyridine, Amino N 9 23.0(λex: 360 nm) 454[22]
Ammonium citrate / Amino N 2.1 13.5(λex: 365 nm) 437[23]
Alanine Ethylenetriamine 40.3 Amino N 8 46.2(λex: 320 nm) 370[26]
Aconitic acid Diethylenetriamine / Amino N 5 81(λex: 365 nm) 435[27]
Glutathione Formamide 30.7 Pyridine, Pyrrolic,Graphitic N 2.9 16.8(λex: 420 nm) 683[28]
Citric acid Formamide 11 Pyrrolic, Graphitic N 4 22.9(λex: 540 nm) 640[29]
Glutamic acid Phenylenediamine 44 Pyridinic, Pyrrolic, Graphitic N 7.6 36(λex: 600 nm) 750[30]
Phenylenediamine 20.1 Pyridinic, Pyrrolic, Amino N 10 26.1(λex: 510 nm) 608[31]
图1 吡啶氮增加碳点PL强度的图示:大部分吡啶氮在碳骨架内部并形成电子陷阱,吡咯氮则分布在边缘。因此,内部结构中含有吡啶氮的N-CDots-1比N-CDots-2更容易形成电子陷阱,显示更强的PL,电子陷阱可以将电子捕获形成电子储库[36]
Fig.1 Positive effects of pyridine N on PL intensity. Most pyridine N atoms are always embedded in the center of the carbon skeleton and form a circle trap, whereas the pyrrole N atoms distributed along the edges. Thus, the N-CDots-1 containing pyridine N in internal structure is easier to form electron traps than N-CDots-2, thus showing higher PL intensity. The electron traps can trap electrons as electron reservoirs[36]. Copyright 2018, Elsevier
图2 (a)N-GDos的合成方法和N-GDots的大小随加热时间变化的示意图;(b)N-GDots的UV-vis-NIR吸收光谱随其尺寸的变化;(c)375 nm激光激发下N-GDos的PL光谱随其尺寸的变化;(d)808 nm激光激发下的N-GDots的近红外PL光谱[25]
Fig.2 (a) Schematic representation of the synthesis of N-GDos and size of the N-GDots as a function of heating time. (b) The size-dependent UV-vis-NIR absorption of N-GDots. (c) Size-dependent visible PL spectra of N-GDos excited by 375 nm laser. (d) NIR PL spectra of the N-GDots excited by 808 nm laser[25]. Copyright 2014, American Chemical Society
表2 一些S,P或B-CDots的前驱体,结构和荧光性能
Table 2 Precursor, structure, and fluorescence performance of some S-, P-, or B-CDots
Precursor Heteroatom/C
ratio/%		 Heteroatom-related bond Average
diameter/nm		 QY/% Max λem/nm
Carbon source Heteroatom source
Sodium citrate Sodium thiosulfate / C—S 4.6 67 (λex: 350 nm) 440[48]
Thiomalic acid Sulfuric acid 18 C—S—C 1.5 11.8(λex: 340 nm) 446[44]
Dextrose Disodium phosphate / / 2.8 6.73(λex: 350 nm) 452[61]
Carbohydrates (glucose, etc.) Phosphoric acid / / 5 7(λex: 385 nm) 600[49]
Citric acid Sodium tetraphenylborate / B4C, BC3, BC2O, BCO2 8 42(λex: 350 nm) 443[52]
Vinylphenylboronic acid Boric acid 5 B4C, B—O, B=C 4.6 / /[53]
Citric acid Boric acid 32.8 B—O, B—C 31.9 40.4(λex: 340 nm) 430[62]
Hydroquinone Boron tribromide 8.5 B—O, B—C 16 14.8(λex: 368 nm) 440[63]
Sucrose Boric acid 9 B—O, B—C, BC2O, BCO2 4.5 2.7(λex: 450 nm) 680[64]
图3 (a)计算模型:含有磷酸酯基或磺酸盐的并苯单元;(b)含有磷酸酯基(P-MO)或磺酸盐(S-MO)的模型的HOMO-LUMO和分子轨道图[51]
Fig.3 (a) Computational models: coronene units containing phosphate group or sulphonate group. (b) HOMO-LUMO gaps and molecule orbit plots of the model containing phosphate groups (P-MO) or sulfonate groups (S-MO)[51]. Copyright 2018, Springer Nature
表3 B-CDots和N-CDots的非线性光学性能参数[54]
Table 3 Values of the nonlinear optical parameters belong to B-CDots and N-CDots reported in ref[54]
Sample Concentration (C) (mg.mL-1) χ(3)(×10-15 esu) χ(3)/C(×10-15 esu·L·g-1) χ(3)(×10-13 esu) χ(3)/C(×10-13 esu·L·g-1)
532 nm, 35 ps 532 nm, 4 ns
B-CDots 0.58 2.9 ± 0.2 5.0 ± 0.3 5.0 ± 0.3 8.6 ± 0.5
0.29 1.8 ± 0.2 6.2 ± 0.7 2.5 ± 0.1 8.6 ± 0.3
N-CDots 5.0 1.0 ± 0.4 0.2 ± 0.08 10.4 ± 0.7 2.1 ± 0.1
2.9 0.2 ± 0.05 0.07 ± 0.02 6.4 ± 0.5 2.2 ± 0.2
图4 (a)不同浓度B-GDots下的T1-MR和R1-MRI图。(b)1/T1随B-GDots浓度的变化关系。斜率为弛豫率 r 1 [58]
Fig.4 (a) T1-weighted MR images and R1 maps of MRI phantom images of B-GDots at different concentrations. (b) Plot of 1/T1 as a function of B-GDots concentration. The slope of the curve is defined as the specific relaxivity of r 1 [58]. Copyright 2016, John Wiley and Sons
图5 O-CDots,N-CDots和N,S-CDots的荧光机理:(1)从基态激发并被表面态俘获的电子;(2)激发态电子通过非辐射途径回到基态;(3)激发态电子通过辐射途径回到基态。引入的S原子似乎能够消除O原子掺杂的表面态(O-states)并增强N原子掺杂的表面态(N-states),从而导致O-states在N,S-CDots中几乎消失[47]
Fig.5 Representation of the fluorescence mechanism of O-CDots, N-CDots, and N, S-CDots. (1) Electrons excited from the ground state and trapped by the surface states, (2) excited electrons return to the ground state via a nonradiative route, and (3) excited electrons return to the ground state via a radiative route. The introduced sulfur atoms seem to be able to eliminate the O-states and enhance the N-state, leading to that the original O-states are nearly neglected in the N, S-CDots[47]. Copyright 2013, John Wiley and Sons
表4 一些共掺杂CDots的前驱体,结构和荧光性能
Table 4 Precursor, structure, and fluorescence performance of some codoped CDots
Precursor Products Heteroatom-related bonds Average diameter/nm QY/% Max λem/nm
Carbon source Heteroatom source
Citric acid L-cysteine N, S-CDots Pyridinic, Pyrrolic N; C—S—C 7 73(λex: 345 nm) 415[47]
α-Lipoic acid,
Ethylenediamine		 Pyridinic, Pyrrolic, Graphitic N—C—S—, —C—SOx; (x = 2, 3, 4) 2.7 54.4(λex: 390 nm) 472[77]
Sodium citrate Sulfamide C—N—C, N—C, N—H; —C—SOx(x = 3, 4) 8 55 (λex: 350 nm) 440[78]
Citric acid Diethylenetriamine,Phosphoric acid N, P-CDots Pyridinic, Pyrrolic, Graphitic N;C—P 2 70 (λex: 360 nm) 452[71]
Citric acid monohydrate Diammonium hydrogen
phosphate		 C—N—C,N—H;C— PO 4 3 - 2.7 59 (λex: 340 nm) 440[79]
Diethylenetriaminepenta
(Methylene-phosphonic
acid), m-
Phenylenediamine		 —NH+—, —C＝NH+;P—C, P—O 2.9 32(λex: 440 nm) 510[80]
Citric acid Ethylene diamine,
Phosphoric acid		 Tertiary amines, Quaternary-N, N—H;C3—P, C—PO3 and/or C2—PO2, C—O—P 4.5 30 (λex: 340 nm) (blue)
78(λex: 450 nm) (green)		 Dual emission
430, 500[81]
m-Phenylenediamine, Ethylenediamine, Phosphoric acid Tertiary amines, Pyridinic, Pyrrolic N, N—H;P—X aromatic, P—O groups 8.1 51(λex: 340 nm) (blue)
38 (λex: 450 nm) (green)		 Dual emission
450, 510[82]
Diethylenetriamine,boric
acid		 N, B-CDots Pyrridinic, Pyrrolic, Graphitic N
B—C, BC3, BC2O, BCO2		 2 39 (λex: 360 nm) 452[71]
Sucrose Urea, Boric acid Pyridinic, Pyrrolic, Graphitic N,B—C, B—N, BC2O, BCO2 4.5 14.2 (λex: 365 nm) 450[83]
Citric acid Urea, Boric acid B—O, B—O—C, B—N 20 /(λex: 355 nm) 455[84]
p-Phenylenediamine, 3-
Formylphenylboronic acid		 / 8.1 36.5 (λex: 400 nm) 560[85]
3-Aminophenylboronic acid / 5 /(λex: 400 nm) 500[86]
N-(4-hydroxyphenyl)
glycine, Boric acid		 B—N, B—C, and C—N 3 23.7(λex: 365 nm) 500[87]
图6 未掺杂(左)和纳米半导体在表面掺杂(右)的碳点的示意图[88]
Fig.6 Cartoon illustrations of nondoped (left) and surface-doped (right) carbon dots with nanoscale semiconductors[88]. Copyright 2011, Royal Society of Chemistry
图7 (a)在不同DEA浓度下,DMF溶液中的PVK-CDots(△,激发波长为440 nm)和二氯苯溶液中的PVK-C60(?,激发波长为540 nm)的荧光强度的Stern-Volmer猝灭图;(b)在不同DNT浓度下,DMF溶液中PVK-CDots的荧光强度(激发波长为440 nm)的Stern-Volmer猝灭图[111]
Fig.7 (a) Stern-Volmer quenching plots for fluorescence intensities of the PVK-CDots in DMF solution (△, 440 nm excitation) and the PVK-C60 in dichlorobenzene solution (?, 540 nm excitation) at different DEA concentrations. (b) Stern-Volmer quenching plot for fluorescence intensities (440 nm excitation) of the PVK-CDots in DMF solution at different DNT concentrations[111]
图8 含包裹物的碳点(主-客体碳点,左)和富勒烯(右)[20]
Fig.8 Carbon dots with encapsulated species (host-guest carbon dot, left) versus an endofullerene (right)[20]
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