高等学校化学学报 ›› 2023, Vol. 44 ›› Issue (2): 20220464.doi: 10.7503/cjcu20220464
符芳媚1, 徐梦如1, 梁梓珊1, 黄斯锐1, 李晖1, 张浩然1,2, 李唯1,2, 郑明涛1,2, 雷炳富1,2()
收稿日期:
2022-07-08
出版日期:
2023-02-10
发布日期:
2022-09-15
通讯作者:
雷炳富
E-mail:tleibf@scau.edu.cn
基金资助:
FU Fangmei1, XU Mengru1, LIANG Zishan1, HUANG Sirui1, LI Hui1, ZHANG Haoran1,2, LI Wei1,2, ZHENG Mingtao1,2, LEI Bingfu1,2()
Received:
2022-07-08
Online:
2023-02-10
Published:
2022-09-15
Contact:
LEI Bingfu
E-mail:tleibf@scau.edu.cn
Supported by:
摘要:
以邻苯二胺和盐酸多巴胺为前体, 利用磷酸调节反应体系的pH值(pH=7, 3, 1), 制备了荧光逐渐红移的碳点(CDs): CDs-7(绿光)、 CDs-3(橙光)和CDs-1(红光). 通过透射电子显微镜(TEM)、 拉曼光谱(Raman)、 傅里叶变换红外光谱(FTIR)、 X射线电子能谱(XPS)、 紫外-可见吸收光谱和荧光衰减曲线分析表明, 反应体系pH值的减小促进了前体碳化交联, 导致sp2共轭域尺寸和石墨化程度增加, 从而使CDs的荧光红移. 另外, 酸性环境有利于使CDs表面氧化形成羧基, 促进CDs荧光红移的同时改善了量子效率(QY). 利用CDs-1量子产率高(14.8%)和发光的溶剂依赖特性, 将其作为荧光探针分别检测了乙醇(EtOH)、 N,N-二甲基甲酰胺(DMF)和1,4-二氧六环(DIO)中的痕量水, 检出限分别为0.86%, 0.123%和0.023%, 表明CDs-1在痕量水的检测方面具有应用潜力.
中图分类号:
TrendMD:
符芳媚, 徐梦如, 梁梓珊, 黄斯锐, 李晖, 张浩然, 李唯, 郑明涛, 雷炳富. 共轭尺寸和表面氧化协同触发的红色荧光碳点用于有机溶剂中痕量水的检测. 高等学校化学学报, 2023, 44(2): 20220464.
FU Fangmei, XU Mengru, LIANG Zishan, HUANG Sirui, LI Hui, ZHANG Haoran, LI Wei, ZHENG Mingtao, LEI Bingfu. Conjugate Size and Surface Oxidation Synergistically Trigger Red Fluorescence in Carbon Dots for Detecting Trace Water in Organic Solvents. Chem. J. Chinese Universities, 2023, 44(2): 20220464.
No. | m(CDs⁃1)/μg | Volume/μL | Water content(%) | No. | m(CDs⁃1)/μg | Volume/μL | Water content(%) | ||
---|---|---|---|---|---|---|---|---|---|
DMF/EtOH | H2O | DMF/EtOH | H2O | ||||||
1 | 200 | 1800 | 0 | 0 | 10 | 200 | 1400 | 400 | 20 |
2 | 200 | 1794 | 6 | 0.3 | 11 | 200 | 1300 | 500 | 25 |
3 | 200 | 1788 | 12 | 0.6 | 12 | 200 | 1200 | 600 | 30 |
4 | 200 | 1780 | 20 | 1 | 13 | 200 | 1100 | 700 | 35 |
5 | 200 | 1740 | 60 | 3 | 14 | 200 | 1000 | 800 | 40 |
6 | 200 | 1700 | 100 | 5 | 15 | 200 | 900 | 900 | 45 |
7 | 200 | 1660 | 140 | 7 | 16 | 200 | 800 | 1000 | 50 |
8 | 200 | 1600 | 200 | 10 | 17 | 200 | 700 | 1100 | 55 |
9 | 200 | 1500 | 300 | 15 | 18 | 200 | 600 | 1200 | 60 |
Table 1 Preparation of DMF/EtOH detection solutions with different water contents ranging from 0—60%
No. | m(CDs⁃1)/μg | Volume/μL | Water content(%) | No. | m(CDs⁃1)/μg | Volume/μL | Water content(%) | ||
---|---|---|---|---|---|---|---|---|---|
DMF/EtOH | H2O | DMF/EtOH | H2O | ||||||
1 | 200 | 1800 | 0 | 0 | 10 | 200 | 1400 | 400 | 20 |
2 | 200 | 1794 | 6 | 0.3 | 11 | 200 | 1300 | 500 | 25 |
3 | 200 | 1788 | 12 | 0.6 | 12 | 200 | 1200 | 600 | 30 |
4 | 200 | 1780 | 20 | 1 | 13 | 200 | 1100 | 700 | 35 |
5 | 200 | 1740 | 60 | 3 | 14 | 200 | 1000 | 800 | 40 |
6 | 200 | 1700 | 100 | 5 | 15 | 200 | 900 | 900 | 45 |
7 | 200 | 1660 | 140 | 7 | 16 | 200 | 800 | 1000 | 50 |
8 | 200 | 1600 | 200 | 10 | 17 | 200 | 700 | 1100 | 55 |
9 | 200 | 1500 | 300 | 15 | 18 | 200 | 600 | 1200 | 60 |
No. | m(CDs⁃1)/μg | Volume/μL | Water content(%) | No. | m(CDs⁃1)/μg | Volume/μL | Water content(%) | ||
---|---|---|---|---|---|---|---|---|---|
DIO | H2O | DIO | H2O | ||||||
1 | 200 | 1800 | 0 | 0 | 12 | 200 | 1660 | 140 | 7 |
2 | 200 | 1798 | 2 | 0.1 | 13 | 200 | 1640 | 160 | 8 |
3 | 200 | 1794 | 6 | 0.3 | 14 | 200 | 1620 | 180 | 9 |
4 | 200 | 1790 | 10 | 0.5 | 15 | 200 | 1600 | 200 | 10 |
5 | 200 | 1786 | 14 | 0.7 | 16 | 200 | 1500 | 300 | 15 |
6 | 200 | 1780 | 20 | 1 | 17 | 200 | 1400 | 400 | 20 |
7 | 200 | 1760 | 40 | 2 | 18 | 200 | 1300 | 500 | 25 |
8 | 200 | 1740 | 60 | 3 | 19 | 200 | 1200 | 600 | 30 |
9 | 200 | 1720 | 80 | 4 | 20 | 200 | 1000 | 800 | 40 |
10 | 200 | 1700 | 100 | 5 | 21 | 200 | 800 | 1000 | 50 |
11 | 200 | 1680 | 120 | 6 | 22 | 200 | 600 | 1200 | 60 |
Table 2 Preparation of DIO detection solutions with different water contents ranging from 0—60%
No. | m(CDs⁃1)/μg | Volume/μL | Water content(%) | No. | m(CDs⁃1)/μg | Volume/μL | Water content(%) | ||
---|---|---|---|---|---|---|---|---|---|
DIO | H2O | DIO | H2O | ||||||
1 | 200 | 1800 | 0 | 0 | 12 | 200 | 1660 | 140 | 7 |
2 | 200 | 1798 | 2 | 0.1 | 13 | 200 | 1640 | 160 | 8 |
3 | 200 | 1794 | 6 | 0.3 | 14 | 200 | 1620 | 180 | 9 |
4 | 200 | 1790 | 10 | 0.5 | 15 | 200 | 1600 | 200 | 10 |
5 | 200 | 1786 | 14 | 0.7 | 16 | 200 | 1500 | 300 | 15 |
6 | 200 | 1780 | 20 | 1 | 17 | 200 | 1400 | 400 | 20 |
7 | 200 | 1760 | 40 | 2 | 18 | 200 | 1300 | 500 | 25 |
8 | 200 | 1740 | 60 | 3 | 19 | 200 | 1200 | 600 | 30 |
9 | 200 | 1720 | 80 | 4 | 20 | 200 | 1000 | 800 | 40 |
10 | 200 | 1700 | 100 | 5 | 21 | 200 | 800 | 1000 | 50 |
11 | 200 | 1680 | 120 | 6 | 22 | 200 | 600 | 1200 | 60 |
Element | Function group | Functional group proportion(%) | |||
---|---|---|---|---|---|
CDs⁃7 | CDs⁃3 | CDs⁃1 | |||
C1s | C=C | 41.35 | 44.85 | 49.84 | |
C—N | 25.97 | 45.42 | 8.18 | ||
C—O | 29.19 | 6.30 | 37.13 | ||
COOH | 3.49 | 3.44 | 4.84 | ||
N1s | Pyridine N | 0 | 4.23 | 32.16 | |
Pyrrolic N | 62.19 | 69.53 | 49.84 | ||
Graphitic N | 27.40 | 9.29 | 13.62 | ||
Amino N | 10.41 | 16.94 | 4.39 | ||
O1s | C=O | 20.32 | 28.68 | 54.89 | |
O—H | 79.48 | 71.32 | 45.11 |
Table 3 Data analysis of XPS C1s, N1s and O1s spectra of CDs-7, CDs-3 and CDs-1
Element | Function group | Functional group proportion(%) | |||
---|---|---|---|---|---|
CDs⁃7 | CDs⁃3 | CDs⁃1 | |||
C1s | C=C | 41.35 | 44.85 | 49.84 | |
C—N | 25.97 | 45.42 | 8.18 | ||
C—O | 29.19 | 6.30 | 37.13 | ||
COOH | 3.49 | 3.44 | 4.84 | ||
N1s | Pyridine N | 0 | 4.23 | 32.16 | |
Pyrrolic N | 62.19 | 69.53 | 49.84 | ||
Graphitic N | 27.40 | 9.29 | 13.62 | ||
Amino N | 10.41 | 16.94 | 4.39 | ||
O1s | C=O | 20.32 | 28.68 | 54.89 | |
O—H | 79.48 | 71.32 | 45.11 |
Fig.4 PL excitation and emission spectra under different excitation of CDs⁃7(A), CDs⁃3(B) and CDs⁃1(C) in ethanol, photographs of three types of CD ethanol solutions taken under daylight and 365 nm UV lamp irradiation(D), UV⁃Vis absorption spectra(E) and PL decay curves(F) of CDs⁃7, CDs⁃3 and CDs⁃1
Sample | τ1/ns | B1 | τ2/ns | B2 | τ3/ns | B3 | τ(avg)/ns | X2 |
---|---|---|---|---|---|---|---|---|
CDs⁃7 | 0.5027 | 0.0484 | 3.647 | 0.0542 | 6.268 | 0.0223 | 4.50 | 1.0950 |
CDs⁃3 | 0.6430 | 0.0370 | 2.417 | 0.0633 | 7.957 | 0.0012 | 2.47 | 1.1244 |
CDs⁃1 | 2.1980 | 0.0956 | 9.565 | 0.0003 | — | — | 2.30 | 1.1970 |
Table 4 PL lifetimes of CDs-7, CDs-3 and CDs-1*
Sample | τ1/ns | B1 | τ2/ns | B2 | τ3/ns | B3 | τ(avg)/ns | X2 |
---|---|---|---|---|---|---|---|---|
CDs⁃7 | 0.5027 | 0.0484 | 3.647 | 0.0542 | 6.268 | 0.0223 | 4.50 | 1.0950 |
CDs⁃3 | 0.6430 | 0.0370 | 2.417 | 0.0633 | 7.957 | 0.0012 | 2.47 | 1.1244 |
CDs⁃1 | 2.1980 | 0.0956 | 9.565 | 0.0003 | — | — | 2.30 | 1.1970 |
Fig.6 Emission spectra(A, E, I) and normalized emission spectra(B, F, J) of CDs⁃1 dispersed in EtOH(A, B), DMF(E, F) and DIO(I, J) with different water contents, linear relationship between emission peak and fluorescence intensity of CDs⁃1 dispersed in EtOH(C, D), DMF(G, H) and 1,4⁃dioxane (K, L) and water contentInsets of (B), (F) and (J): visual PL photos of CDs⁃1 dispersed in EtOH, DMF and DIO with various water contents excited at 365 nm.
Material | Method | Response ranges and detection limit(%) | R2 | Ref. |
---|---|---|---|---|
Ethylenediamine β⁃Resorcylic acid | Emission peak | 0—2, 0.37(Acetone) 0—2, 0.36(THF) | 0.970 0.973 | [ |
o⁃Phenylenediamine | Emission peak | 0—3, 0.19(Acetone) 0—3, 0.13(THF) 0—3, 0.18(Acetonitrile) | 0.971 | [ |
2,5⁃Dihydroxyterephthalic acid | Ratiometric fluorescent | 0.2—6, 0.052(Ethanol) 0.5—8, 0.085(Acetonitrile) 0.8—8, 0.10(THF) 1—8, 0.18(1,4⁃Dioxane) | 0.996 0.992 0.997 0.992 | [ |
1,4⁃Phenylene diisocyanate | Intensity/Emission peak | 0—1.5, 0.006(DMF) 0—5, 0.004(Ethyl acetate) | 0.968 0.989 | [ |
Ethylenediamine and Catechol | Intensity/Emission peak | 0.1—2.5, 0.07(Acetone) 2—20, 0.46(Methanol) | 0.995 0.993 | [ |
o⁃Phenylenediamine and Dopamine HCl | Emission peak Intensity | 0—10, 4.11(EtOH) 0—7, 0.123(DMF) 0—1, 0.023(DIO) 0—15, 0.86(EtOH) 010, 0.33(DMF) | 0.963 0.993 0.997 0.994 0.946 | This work |
Table 5 Comparison of determination methods of trace water in organic solvents
Material | Method | Response ranges and detection limit(%) | R2 | Ref. |
---|---|---|---|---|
Ethylenediamine β⁃Resorcylic acid | Emission peak | 0—2, 0.37(Acetone) 0—2, 0.36(THF) | 0.970 0.973 | [ |
o⁃Phenylenediamine | Emission peak | 0—3, 0.19(Acetone) 0—3, 0.13(THF) 0—3, 0.18(Acetonitrile) | 0.971 | [ |
2,5⁃Dihydroxyterephthalic acid | Ratiometric fluorescent | 0.2—6, 0.052(Ethanol) 0.5—8, 0.085(Acetonitrile) 0.8—8, 0.10(THF) 1—8, 0.18(1,4⁃Dioxane) | 0.996 0.992 0.997 0.992 | [ |
1,4⁃Phenylene diisocyanate | Intensity/Emission peak | 0—1.5, 0.006(DMF) 0—5, 0.004(Ethyl acetate) | 0.968 0.989 | [ |
Ethylenediamine and Catechol | Intensity/Emission peak | 0.1—2.5, 0.07(Acetone) 2—20, 0.46(Methanol) | 0.995 0.993 | [ |
o⁃Phenylenediamine and Dopamine HCl | Emission peak Intensity | 0—10, 4.11(EtOH) 0—7, 0.123(DMF) 0—1, 0.023(DIO) 0—15, 0.86(EtOH) 010, 0.33(DMF) | 0.963 0.993 0.997 0.994 0.946 | This work |
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