Novel Diazocrowns with Pyrrole Residue as Lead(II)Colorimetric Probes
Abstract
:1. Introduction
2. Materials and Methods
2.1. General
2.2. Synthesis of Crowns 3 and 4
2.2.1. 1,5-bis(2-nitrophenoxy)pentane (7) and 1,10-bis(2-nitrophenoxy)decane (8)
2.2.2. 1,5-bis(2-aminophenoxy)pentane (5) and 1,10-bis(2-aminophenoxy)decane (6)
2.2.3. Preparation of New Diazocrown 3 and 4
- A: Diaminopodand 5 or 6 (1 mmol) and concentrated hydrochloric acid (0.5 mL) in water (20 mL) (DMF or THF in needed amount can be added to increase solubility of amines);
- B: Sodium nitrite (2 mmol) in water (30 mL);
- C: Pyrrole (1 mmol, 0.07 mL) and sodium hydroxide (0.20 g, 5 mmol) in water (30 mL).
2.2.4. Preparation of Solid Complexes of Crowns 1–4 with Lead(II) Perchlorate
2.3. Lipophilicity Determination
2.4. X-ray Structure Determination
2.5. Cation Binding Studies
2.6. Preparation of Sensing Layers
2.6.1. Test Strips
2.6.2. Optodes
3. Results and Discussion
3.1. Synthesis
3.2. X-ray Structure of 3
3.3. Heavy Metal Cation Complexation Studies
3.4. Possible Applications
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
Appendix A
References
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Crown | Model | m/z * | Figure |
---|---|---|---|
1 | [3(C20H18N5O3)−][3Pb2+][2ClO4−] | 1950 | S11a |
[2C20H19N5O3][(C20H18N5O3)−][2Pb2+][2ClO4−] | 1745 | S11b | |
[2(C20H18N5O3)−][C20H19N5O3][2Pb2+][ClO4−] | 1644 | S11c | |
[2(C20H18N5O3)−][2Pb2+][ClO4−] | 1267 | S11d | |
[(C20H18N5O3)−][Pb2+] | 584 | S11e | |
2 | [3(C22H22N5O4)−][3Pb2+][2ClO4−] | 2082 | S12a |
[2C22H23N5O4][(C22H22N5O4)−][2Pb2+][2ClO4−] | 1876 | S12b | |
[2(C22H22N5O4)−][C22H23N5O4][2Pb2+][ClO4−] | 1776 | S12c | |
[2(C22H22N5O4)−][2Pb2+][ClO4−] | 1355 | S12d | |
[(C22H22N5O4)-][Pb2+] | 628 | S12e | |
3 | [3(C21H20N5O2)−][3Pb2+][2ClO4−] | 1944 | S13a |
[2(C21H20N5O2)−][C21H21N5O2][2Pb2+][ClO4−] | 1638 | S13b | |
[2(C21H20N5O2)−][2Pb2+][ClO4−] | 1263 | S13c | |
[(C21H20N5O2)−][C21H21N5O2][Pb2+] | 957 | S13d | |
[(C21H20N5O2)−][Pb2+] | 582 | S13e | |
4 | [3(C26H30N5O2)−][3Pb2+][2ClO4−] | 2154 | S14a |
[2C26H31N5O2][(C26H30N5O2)−][2Pb2+][2ClO4−]- | 1948 | S14b | |
[2(C26H30N5O2)−][C26H31N5O2][2Pb2+][ClO4−] | 1847 | S14c | |
[2(C26H30N5O2)−][2Pb2+][ClO4−] | 1403 | S14d | |
[(C26H30N5O2)−][Pb2+] | 652 | S14e |
Water Sample | Added Pb(II) (mol/dm3) | Found Pb(II) (mol/dm3) | Recovery (%) | ||
---|---|---|---|---|---|
A = f([Pb(II)]) | A = f(log [Pb(II)]) | A = f([Pb(II)]) | A = f(log [Pb(II)]) | ||
Tap water 1 | no addition | <LOD | - | ||
2.00 × 10−6 | 1.95 × 10−6 | - | 97.68 | - | |
4.00 × 10−6 | 3.94 × 10−6 | - | 98.58 | - | |
8.00 × 10−6 | 8.19 × 10−6 | 7.81 × 10−6 | 102.42 | 97.67 | |
2.00 × 10−5 | - | 1.97 × 10−5 | - | 98.54 | |
4.00 × 10−5 | - | 4.05 × 10−5 | - | 101.18 | |
8.00 × 10−5 | - | 8.14 × 10−5 | - | 101.77 | |
Tap water 2 | no addition | <LOD | - | ||
2.00 × 10−6 | 2.04 × 10−6 | - | 102.19 | - | |
4.00 × 10−6 | 4.03 × 10−6 | - | 100.84 | - | |
8.00 × 10−6 | 8.10 × 10−6 | 7.89 × 10−6 | 101.29 | 98.68 | |
2.00 × 10−5 | - | 2.01 × 10−5 | - | 100.59 | |
4.00 × 10−5 | - | 3.96 × 10−5 | - | 99.12 | |
8.00 × 10−5 | - | 8.06 × 10−5 | - | 100.73 |
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Galiński, B.; Luboch, E.; Chojnacki, J.; Wagner-Wysiecka, E. Novel Diazocrowns with Pyrrole Residue as Lead(II)Colorimetric Probes. Materials 2021, 14, 7239. https://doi.org/10.3390/ma14237239
Galiński B, Luboch E, Chojnacki J, Wagner-Wysiecka E. Novel Diazocrowns with Pyrrole Residue as Lead(II)Colorimetric Probes. Materials. 2021; 14(23):7239. https://doi.org/10.3390/ma14237239
Chicago/Turabian StyleGaliński, Błażej, Elżbieta Luboch, Jarosław Chojnacki, and Ewa Wagner-Wysiecka. 2021. "Novel Diazocrowns with Pyrrole Residue as Lead(II)Colorimetric Probes" Materials 14, no. 23: 7239. https://doi.org/10.3390/ma14237239