Acridino-Diaza-20-Crown-6 Ethers: New Macrocyclic Hosts for Optochemical Metal Ion Sensing
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis
2.2. Spectral Properties
2.3. Studies on Metal Ion Complexation
2.4. Acid–Base Properties
2.5. Coordination Ability toward Anions
3. Conclusions
4. Experimental Methods
4.1. Chemicals, Apparatus and Measurements
4.2. Evaluation of the Results
4.3. Synthesis of the New Compounds
4.3.1. Optimized Synthesis of 4,5-Bis(bromomethyl)acridine (5)
4.3.2. Preparation of N,N′-(Acridine-4,5-diylbis(methylene))bis(2-methylpropan-2-amine) (7)
4.3.3. Preparation of 1,1′-(Acridine-4,5-diyl)bis(N-benzylmethanamine) (11)
4.3.4. Preparation of N,N′-(Acridine-4,5-diylbis(methylene))bis(prop-2-en-1-amine) (14)
4.3.5. Preparation of 7,19-Dibenzyl-10,13,16-trioxa-7,19,27-triazatetracyclo [23.3.1.0⁵,2⁸.021,2⁶]nonacosa-1,3,5(28),21,23,25(29),26-heptaene (12)
4.3.6. Preparation of 7,19-Bis(prop-2-en-1-yl)-10,13,16-trioxa-7,19,27-triazatetracyclo[2 3.3.1.0⁵,2⁸.021,2⁶]nonacosa-1,3,5(28),21,23,25(29),26-heptaene (15)
4.3.7. Preparation of 10,13,16-Trioxa-7,19,27-triazatetracyclo[2 3.3.1.0⁵,2⁸.021,2⁶]nonacosa-1,3,5(28),21,23,25(29),26-heptaene (17) by the debenzylation of (12)
4.3.8. Preparation of 10,13,16-Trioxa-7,19,27-triazatetracyclo[2 3.3.1.0⁵,2⁸.021,2⁶]nonacosa-1,3,5(28),21,23,25(29),26-heptaene (17) starting from (15)
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
Sample Availability
References
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Experiment No. | BMME (molar eq.) 1 | Temperature (°C) | Reaction Time (h) | Yield (%) |
---|---|---|---|---|
1 | 4 | 50 | 18 | 48 [55] |
2 | 4 | 50 | 24 | 49 |
3 | 4 | 65 | 24 | 51 |
4 | 4 | 65 | 48 | 55 (chrom) 2/79 (cryst) 3 |
5 | 6 | 65 | 48 | 37 |
6 | 4 | 75 | 48 | 40 |
Preferred Ion | Macrocycle | Peak Wavelength of the Complex 1 [nm] | LOD [M] | logK |
---|---|---|---|---|
Zn2+ | 12 | 444 | 7.0 × 10−8 | 5.5 ± 0.1 |
15 | 434 | 1.7 × 10−7 | 5.6 ± 0.2 | |
17 | 446 | 2.3 × 10−6 | 5.1 ± 0.3 | |
Al3+ | 12 | 437 | 2.2 × 10−7 | 5.5 ± 0.3 |
15 | 412 | 5.9 × 10−8 | 5.6 ± 0.2 | |
17 | 419 | 1.9 × 10−6 | 4.9 ± 0.1 | |
Bi3+ | 12 | 439 | 2.2 × 10−7 | 4.9 ± 0.3 |
15 | 483 | 4.6 × 10−6 | 5.0 ± 0.1 | |
17 | 438 | 2.0 × 10−7 | 4.8 ± 0.1 |
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Golcs, Á.; Kovács, K.; Vezse, P.; Tóth, T.; Huszthy, P. Acridino-Diaza-20-Crown-6 Ethers: New Macrocyclic Hosts for Optochemical Metal Ion Sensing. Molecules 2021, 26, 4043. https://doi.org/10.3390/molecules26134043
Golcs Á, Kovács K, Vezse P, Tóth T, Huszthy P. Acridino-Diaza-20-Crown-6 Ethers: New Macrocyclic Hosts for Optochemical Metal Ion Sensing. Molecules. 2021; 26(13):4043. https://doi.org/10.3390/molecules26134043
Chicago/Turabian StyleGolcs, Ádám, Korinna Kovács, Panna Vezse, Tünde Tóth, and Péter Huszthy. 2021. "Acridino-Diaza-20-Crown-6 Ethers: New Macrocyclic Hosts for Optochemical Metal Ion Sensing" Molecules 26, no. 13: 4043. https://doi.org/10.3390/molecules26134043