Azobenzene-Containing Schiff-Bases—Syntheses and Dyes Applications
Abstract
:1. Introduction
2. Syntheses and Structures of Azobenzene-Containing Schiff-Bases
2.1. Schiff Base Synthesis
2.1.1. Main Imine Syntheses
2.1.2. Aniline to Arylamines
2.1.3. Two Aldehydes and Aniline
2.1.4. Unusual Imine Synthesis
2.1.5. Complex Synthesis: Aldehyde Coordination First, Imine Synthesis on Metal
2.2. Main Azo Schiff Base Synthetic Method
2.2.1. Azobenzene Synthesis by Mills Reaction
2.2.2. Azo Schiff Base Synthesis by Diazotization Method
2.2.3. Structural Variations Due to Orientation When the Azo and Imine Groups Are in the Same Benzene Ring
2.2.4. Azoaldehyde, Schiff Base and Complex Synthesis
2.2.5. If There Are More than One Amino Group, Can a Schiff Base Ligand Be Formed First?
2.2.6. Adjustment of the Number of Imines
2.2.7. Unusual Reactions
3. Azobenzene-Containing Schiff-Bases Applications
3.1. Sensors
3.2. Liquid Crystals
3.3. Enzymatic Fuel Cells and Electrode Mediators
3.4. UV-Protection and Anti-Corrosive Effect
3.5. Anticancer and Antibacterials
4. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Klebsiella pneumoniae | Escherichia coli | Staphylococcus aureus | Pseudomonas aeruginosa | Enterococcus faecalis | Bacillus subtilis | Salmonella typhi | Reference | |
---|---|---|---|---|---|---|---|---|
UV2 a | 8 | 7 | 9 | 8 | - | - | - | [104] |
Co(UV2)2 a | 7 | 7 | 8 | 7 | - | - | - | |
Cu(UV2)2 a | 7 | 8 | 8 | 7 | - | - | - | |
UV3(a) b | 64 | 64 | 16 | 64 | 16 | - | - | [105] |
UV3(b) b | 64 | 64 | 16 | 64 | 8 | - | - | |
CuUV3(a) b | 32 | 32 | 16 | 32 | 16 | - | - | |
CuUV3(b) b | 32 | 32 | 16 | 32 | 16 | - | - | |
UV4(a) a | <6 | <6 | <6 | <6 | - | <6 | - | [61] |
UV4(b) a | <6 | <6 | 9–12 | <6 | - | >12 | - | |
UV5(a) c | - | 250 | 32.25 | - | - | 62.5 | 125 | [106] |
UV5(b) c | - | 250 | 3.90 | - | - | 125 | 250 | |
UV5(c) c | - | 250 | 7.81 | - | - | 15.63 | 250 | |
Zn(UV5(a))2 c | - | 62.5 | 7.81 | - | - | 7.81 | 125 | |
Zn(UV5(b))2 c | - | 250 | 15.63 | - | - | 31.25 | 250 | |
Zn(UV5(c))2 c | - | 62.5 | 3.90 | - | - | 7.81 | 125 | |
UV6 a | - | 0 | 5–10 | 10 | - | 0 | - | [52] |
Mn(UV6)2 a | - | 0 | 5–10 | 10–15 | - | 5–10 | - | |
Ni(UV6)2 a | - | 0 | 0 | 10–15 | - | 0 | - | |
Co(UV6)2 a | - | 10–15 | 10–15 | 10–15 | - | 0 | - | |
Cu(UV6)2 a | - | 10–15 | 0 | 10–15 | - | 0 | - | |
Zn(UV6)2 a | - | 0 | 0 | 20 | - | 0 | - | |
Pd(UV6)OAc a | - | 15–20 | 10–15 | 10–15 | - | 10–15 | - | |
UV7 b | - | 100 | 200 | 350 | - | 400 | - | [107] |
Co(UV7) b | - | 15 | 10 | 25 | - | 20 | - | |
Ni(UV7) b | - | 25 | 30 | 20 | - | 80 | - | |
Cu(UV7) b | - | 25 | 10 | 20 | - | 15 | - | |
Zn(UV7) b | - | 45 | 90 | 100 | - | 200 | - | |
UV8a a | - | 19 | 17 | 16 | - | 20 | - | [108] |
UV8b a | - | 22 | 20 | 18 | - | 22 | - | |
VO(UV8a)SO4 a | - | 24 | 22 | 22 | - | 24 | - | |
VO(UV8b)SO4 a | - | 16 | 20 | 21 | - | 20 | - | |
Co(UV9a)2 a | 16.17 | 16.67 | 20.83 | - | - | - | - | [109] |
Cu(UV9a)2 a | 16.00 | 15.83 | 18.33 | - | - | - | - | |
Ni(UV9a)2 a | 14.67 | 0 | 14.83 | - | - | - | - | |
Co(UV9b)2 a | 16.17 | 15.50 | 16.83 | - | - | - | - | |
Cu(UV9b)2 a | 15.83 | 14.83 | 14.50 | - | - | - | - | |
Ni(UV9b)2 a | 16.67 | 0 | 15.17 | - | - | - | - | |
UV10a a | 20 | 21 | 20 | - | - | - | - | [110] |
UV10b a | 19 | 18 | 18 | - | - | - | - | |
UV10c a | 21 | 20 | 17 | - | - | - | - | |
UV10d a | 20 | 49 | 45 | - | - | - | - | |
UV10e a | 25 | 32 | 35 | - | - | - | - | |
UV11 a | 9 | 6 | 12 | - | - | - | 15 | [111] |
CoUV11 a | 9 | 18 | 16 | - | - | - | 18 | |
NiUV11 a | 11 | 22 | 22 | - | - | - | 20 | |
CuUV11 a | 17 | 27 | 19 | - | - | - | 20 | |
CdUV11 a | 17 | 24 | 25 | - | - | - | 21 | |
ZnUV11 a | 19 | 30 | 27 | - | - | - | 26 | |
UV12 a | - | 21 | 23 | - | - | - | - | [112] |
Ni(UV12)2 a | - | 21 | 17 | - | - | - | - | |
UV13 a | - | 19 | 17 | 16 | - | 20 | - | [113] |
Co(UV13)Cl a | - | 22 | 20 | 18 | - | 22 | - | |
Ni(UV13)Cl a | - | 24 | 26 | 20 | - | 24 | - | |
Pd(UV13)Cl a | - | 24 | 22 | 22 | - | 24 | - | |
Pt(UV13)Cl3 a | - | 16 | 20 | 21 | - | 20 | - | |
UV14 a | 9 | 10 | 13 | - | 0 | 12 | - | [114] |
Cu(UV14)2 a | 12 | 12 | 20 | 0 | 15 | 17 | - | |
Co(UV14)2 a | 9 | 11 | 9 | 0 | 0 | 11 | - | |
Ni(UV14)2 a | 11 | 9 | 13 | 0 | 0 | 12 | - |
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Leonard, E.; Takeda, C.; Akitsu, T. Azobenzene-Containing Schiff-Bases—Syntheses and Dyes Applications. Colorants 2024, 3, 53-72. https://doi.org/10.3390/colorants3010004
Leonard E, Takeda C, Akitsu T. Azobenzene-Containing Schiff-Bases—Syntheses and Dyes Applications. Colorants. 2024; 3(1):53-72. https://doi.org/10.3390/colorants3010004
Chicago/Turabian StyleLeonard, Estelle, China Takeda, and Takashiro Akitsu. 2024. "Azobenzene-Containing Schiff-Bases—Syntheses and Dyes Applications" Colorants 3, no. 1: 53-72. https://doi.org/10.3390/colorants3010004