Simple One–Pot Synthesis of Hexakis(2-alkoxy-1,5-phenyleneimine) Macrocycles by Precipitation–Driven Cyclization
Abstract
:1. Introduction
2. Materials and Methods
2.1. Materials and Instruments
2.2. Preparation of Monomers
2.2.1. 2-Alkoxy-5-nitrobenzaldehydes
2.2.2. 2-Alkoxy-5-nitrobenzaldehyde Diethyl Acetals
2.2.3. 2-Alkoxy-5-aminobenzaldehyde Diethyl Acetals
2.3. Synthesis of Hexakis(2-alkoxy-1,5-phenyleneimine) Macrocycles
2.3.1. Hexakis(2-octyloxy-1,5-phenyleneimine) Macrocycle (OcO–Cm6)
2.3.2. Hexakis(2-((S)-(–)-3,7-dimethyloctyloxy)-1,5-phenyleneimine) Macrocycle ((–)BCO–Cm6)
2.3.3. Hexakis(2-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy-1,5-phenyleneimine) Macrocycle (TEGO–Cm6)
3. Results
3.1. Preparation of Monomers
3.2. Synthesis of Hexakis(2-alkoxy-1,5-phenyleneimine) Macrocycles
3.2.1. Hexakis(2-octyloxy-1,5-phenyleneimine) Macrocycle (OcO–Cm6)
3.2.2. Hexakis(2-((S)-(–)-3,7-dimethyloctyloxy)-1,5-phenyleneimine) Macrocycle ((–)BCO–Cm6)
3.2.3. Hexakis(2-(2-(2-methoxyethoxy)ethoxy)ethoxy-1,5-phenyleneimine) Macrocycle (TEGO–Cm6)
4. Conclusions
Supplementary Materials
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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2θ (deg) | d Value (Å) | 2θ (deg) | d Value (Å) |
---|---|---|---|
4.35 * | 20.29 | 17.81 | 4.98 |
6.73 | 13.12 | 18.84 | 4.71 |
8.71 | 10.14 | 20.17 | 4.40 |
12.99 | 6.81 | 21.13 | 4.20 |
13.47 | 6.57 | 23.62 | 3.76 |
16.03 | 5.52 | 24.59 | 3.62 |
Entry | Concentration (mol/L) | Monomer (g) | THF (mL) | H2O (mL) | Gel Time 2 (day) |
---|---|---|---|---|---|
1 | 0.93 | 1.00 | 2.0 | 1.0 | 20 |
2 | 0.46 | 5.01 | 20 | 10 | 20 |
3 | 0.23 | 2.51 | 20 | 10 | 24 |
4 | 0.09 | 1.00 | 20 | 10 | - |
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Matsumoto, T. Simple One–Pot Synthesis of Hexakis(2-alkoxy-1,5-phenyleneimine) Macrocycles by Precipitation–Driven Cyclization. Macromol 2024, 4, 1-22. https://doi.org/10.3390/macromol4010001
Matsumoto T. Simple One–Pot Synthesis of Hexakis(2-alkoxy-1,5-phenyleneimine) Macrocycles by Precipitation–Driven Cyclization. Macromol. 2024; 4(1):1-22. https://doi.org/10.3390/macromol4010001
Chicago/Turabian StyleMatsumoto, Toshihiko. 2024. "Simple One–Pot Synthesis of Hexakis(2-alkoxy-1,5-phenyleneimine) Macrocycles by Precipitation–Driven Cyclization" Macromol 4, no. 1: 1-22. https://doi.org/10.3390/macromol4010001