Meta-Substituted Asymmetric Azobenzenes: Insights into Structure–Property Relationship
Abstract
:1. Introduction
2. Results and Discussion
2.1. Design and Synthesis
2.2. UV–vis Characterization
2.3. Thermal Relaxation
2.4. Computational Studies
2.5. 1H-NMR Analysis
3. Materials and Methods
3.1. General Experimental Details
3.2. Synthetic Procedures and Characterization
- Compound AB-OH.Me, (E)-4-((3,5-dimethylphenyl)diazenyl)phenol. This compound was synthesized as reported in the literature [15]. Concentrated hydrochloric acid (2 mL) was added to a suspension of 3,5-dimethylaniline Ph-NH2.Me (0.606 g, 5.00 mmol, 1 eq) in water (20 mL). The mixture was cooled to 0 °C in an ice bath and stirred vigorously. A solution of NaNO2 (0.380 g, 5.50 mmol, 1.1 eq) in water (3 mL) was then added dropwise to the cooled suspension, and the mixture was stirred for 1 h. In a separate flask, NaOH 5 M (0.999 g, 25.0 mmol, 5 eq) was added to a solution of phenol (0.565 g, 6.00 mmol, 1.2 eq) in water (2 mL), and cooled to 0 °C. The former mixture was then slowly transferred to the solution of phenol and vigorously stirred for 1 h at 0 °C. The resultant precipitate was filtered with vacuo and purified by silica chromatography (dichloromethane/ethyl acetate 9.5:0.5) to give an orange powder (0.404 g, 35.7%). 1H NMR (600 MHz, CDCl3): δ = 7.86 (d, J = 8.8 Hz, 2H), 7.49 (s, 2H), 7.09 (s, 1H), 6.94 (d, J = 8.8 Hz, 2H), 5.08 (s, 1H, OH), 2.41 (s, 6H). 13C NMR (151 MHz, CDCl3): δ = 158.15, 153.06, 147.47, 138.85, 132.32, 125.00, 120.51, 115.90, 21.47. HRMS (ESI, positive mode) m/z calculated for C14H15N2O [M + H]+: 227.1174; found: 227.1179 [40].
- Compound AB-OH.OMe, (E)-4-((3,5-dimethoxyphenyl)diazenyl)phenol. This compound was synthesized adapting a procedure from the literature [40]. Concentrated hydrochloric acid (1.3 mL) was added to a suspension of 3,5-dimethoxyanline Ph-NH2.OMe (0.500 g, 3.26 mmol, 1 eq) in tetrahydrofuran (5 mL). The mixture was cooled to 0 °C in an ice bath and stirred vigorously. A solution of NaNO2 (0.247 g, 3.59 mmol, 1.1 eq) in 1.95 mL of water was then added dropwise to the cooled suspension, and the mixture was stirred for 1 h. In a separate flask, NaOH 5 M (0.652 g, 16.3 mmol, 5 eq) was added to a solution of phenol (0.368 g, 3.91 mmol, 1.2 eq) in 2.6 mL of water, and cooled to 0 °C. The former mixture was then slowly transferred to the solution of phenol and vigorously stirred for 1 h at 0 °C. The reaction mixture was extracted with dichloromethane, the organic layers collected, dried over Na2SO4, filtered, and solvent removed with vacuo. The crude product was purified by silica chromatography using a gradient eluent (dichloromethane 100% → ethyl acetate 100%) to obtain the desired product as a red dark powder (0.377 g, 44.8%). 1H NMR (600 MHz, CDCl3) δ 7.88 (d, J = 8.8 Hz, 2H), 7.08 (s, 2H), 6.95 (d, J = 8.8 Hz, 2H), 6.57 (s, 1H), 5.17 (s, 1H, OH), 3.87 (s, 6H). 13C NMR (151 MHz, CDCl3) δ 161.22, 158.49, 154.68, 147.16, 125.22, 115.96, 103.55, 100.81, 55.75. HRMS (ESI, positive mode) m/z calculated for C14H15N2O3 [M + H]+: 259.1083; found: 259.1082.
- Compound AB-OH.CO2Me, (E)-dimethyl 5-((4-hydroxyphenyl)diazenyl)isophthalate. This compound was synthesized adapting a procedure from the literature [40]. Concentrated hydrochloric acid (0.95 mL) was added to a suspension of dimethyl 5-aminoisophthalate Ph-NH2.CO2Me (0.500 g, 2.39 mmol, 1 eq) in tetrahydrofuran (5 mL). The mixture was cooled to 0 °C in an ice bath and stirred vigorously. A solution of NaNO2 (0.182 g, 2.63 mmol, 1.1 eq) in 1.42 mL of water was then added dropwise to the cooled suspension, and the mixture was stirred for 1 h. In a separate flask, NaOH 5 M (0.476 g, 11.9 mmol, 5 eq) was added to a solution of phenol (0.270 g, 2.87 mmol, 1.2 eq) in 1.92 mL of water, and cooled to 0 °C. The former mixture was then slowly transferred to the solution of phenol and vigorously stirred for 1 h at 0 °C. The reaction mixture was extracted with ethyl acetate, the organic layers collected, dried over Na2SO4, filtered, and solvent removed with vacuo. The crude product was purified by silica chromatography using dichloromethane/ethyl acetate (9.5:0.5) as an eluent, to obtain the desired product as bright orange powder (0.515 g, 68.6%). 1H NMR (600 MHz, CDCl3) δ = 8.75 (s, 1H), 8.70 (s, 2H), 7.94 (d, J = 8.5 Hz, 2H), 6.98 (d, J = 8.5 Hz, 2H), 5.32 (s, 1 H, OH), 4.00 (s, 6H). 13C NMR (151 MHz, CDCl3) δ = 166.06, 159.13, 153.04, 147.11, 131.87, 131.82, 127.74, 125.66, 116.10, 52.72. HRMS (ESI, positive mode) m/z calculated for C16H15N2O5 [M + H]+: 315.0981; found: 315.0983.
- Compound AB.Me, (E)-1-(3,5-dimethylphenyl)-2-(4-methoxyphenyl)diazene. A solution of compound AB-OH.Me (0.100 g, 0.442 mmol, 1 eq), iodomethane (0.033 mL, 0.530 mmol, 1.2 eq), K2CO3 (0.091 g, 0.663 mmol, 1.5 eq), and dimethylformamide (2 mL) was stirred at 7 °C for 24 h. The mixture was allowed to reach room temperature, diluted with ethyl acetate, transferred in a separatory funnel, and washed with water. The organic layers were collected, dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica chromatography (petroleum ether/ethyl acetate = 8:2) to obtain the desired product as a bright orange oil (0.088 g, 83.0%). 1H NMR (600 MHz, CDCl3) δ 7.91 (d, J = 9.0 Hz, 2H), 7.50 (s, 2H), 7.09 (s, 1H), 7.02 (d, J = 9.0 Hz, 2H), 3.89 (s, 3H), 2.41 (s, 6H). 13C NMR (151 MHz, CDCl3) δ 162.06, 153.11, 147.25, 138.81, 132.22, 124.75, 120.48, 114.33, 55.70, 21.40. HRMS (ESI, positive mode) m/z calculated for C15H16N2O [M + H]+: 241.1341; found: 241.1341.
- Compound AB.OMe, (E)-1-(3,5-dimethoxyphenyl)-2-(4-methoxyphenyl)diazene. A solution of compound AB-OH.OMe (0.146 g, 0.566 mmol, 1 eq), iodomethane (0.042 mL, 0.680 mmol, 1.2 eq), K2CO3 (0.117 g, 0.849 mmol, 1.5 eq), and dimethylformamide (2.5 mL) was stirred at 70 °C for 24 h. The mixture was allowed to reach room temperature, diluted with ethyl acetate, transferred in a separatory funnel, and washed with water. The organic layers were collected, dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by silica chromatography (petroleum ether/ethyl acetate = 8:2) to obtain the desired product as a bright orange powder (0.084 g, 54.5%). 1H NMR (600 MHz, CDCl3) δ 7.92 (d, J = 9.4 Hz, 2H), 7.09 (d, 2H), 7.03 (d, J = 9.4 Hz, 2H), 6.58 (s, 1H), 3.90 (s, 3H), 3.88 (s, 6H). 13C NMR (151 MHz, CDCl3) δ 162.32, 161.22, 154.76, 146.99, 124.98, 114.38, 103.49, 100.77, 76.95, 55.74. HRMS (ESI, positive mode) m/z calculated for C15H16N2O3 [M + H]+: 273.1239; found: 273.1238.
- Compound AB.CO2Me, (E)-dimethyl 5-((4-methoxyphenyl)diazenyl)isophthalate. A solution of compound AB-OH.CO2Me (0.100 g, 0.318 mmol, 1 eq), iodomethane (0.024 mL, 0.382 mmol, 1.2 eq), K2CO3 (0.066 g, 0.477 mmol, 1.5 eq) and dimethylformamide (1.5 mL) was stirred at 70 °C for 24 h. The mixture was allowed to reach room temperature, diluted with ethyl acetate, transferred in a separatory funnel, and washed with water. The organic layers were collected, dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica chromatography (dichloromethane 100%) to obtain the desired product as a bright yellow powder (0.033 g, 31.7%). 1H NMR (600 MHz, CDCl3) δ = 8.75 (s, 1H), 8.70 (s, 1H), 7.98 (d, J = 8.7 Hz, 2H), 7.05 (d, J = 8.7 Hz, 2H), 3.99 (s, 6H), 3.91 (s, 3H). 13C NMR (151 MHz, CDCl3) δ = 166.00, 162.90, 153.04, 146.86, 131.75, 127.67, 125.39, 114.48, 55.76, 52.67. HRMS (ESI, positive mode) m/z calculated for C17H16N2O5 [M + H]+: 329.1137; found: 329.1130.
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Sanna, A.L.; Pachova, T.; Catellani, A.; Calzolari, A.; Sforazzini, G. Meta-Substituted Asymmetric Azobenzenes: Insights into Structure–Property Relationship. Molecules 2024, 29, 1929. https://doi.org/10.3390/molecules29091929
Sanna AL, Pachova T, Catellani A, Calzolari A, Sforazzini G. Meta-Substituted Asymmetric Azobenzenes: Insights into Structure–Property Relationship. Molecules. 2024; 29(9):1929. https://doi.org/10.3390/molecules29091929
Chicago/Turabian StyleSanna, Anna Laura, Tatiana Pachova, Alessandra Catellani, Arrigo Calzolari, and Giuseppe Sforazzini. 2024. "Meta-Substituted Asymmetric Azobenzenes: Insights into Structure–Property Relationship" Molecules 29, no. 9: 1929. https://doi.org/10.3390/molecules29091929
APA StyleSanna, A. L., Pachova, T., Catellani, A., Calzolari, A., & Sforazzini, G. (2024). Meta-Substituted Asymmetric Azobenzenes: Insights into Structure–Property Relationship. Molecules, 29(9), 1929. https://doi.org/10.3390/molecules29091929