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Journal articles on the topic 'Azo compounds'

Author: Grafiati

Published: 4 June 2021

Last updated: 30 July 2024

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1

Beck, Karin, Harald Burghard, Gabriele Fischer, Siegfried Hünig, and Petra Reinold. "Azo Cope Rearrangements of Nonstabilized Azo Compounds." Angewandte Chemie International Edition in English 26, no. 7 (July 1987): 672–73. http://dx.doi.org/10.1002/anie.198706721.

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2

Matsui, Masaki, Shigeo Kawamura, Katusoyoshi Shibata, Hiroshige Muramatsu, Motohiro Mitani, Hideo Sawada, and Masaharu Nakayama. "Perfluoroalkylation of azo compounds." Journal of Fluorine Chemistry 57, no. 1-3 (April 1992): 209–17. http://dx.doi.org/10.1016/s0022-1139(00)82833-x.

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3

Kempa, S., L. Wallach, and K. Rueck-Braun. "ChemInform Abstract: Aliphatic Azo Compounds." ChemInform 43, no. 36 (August 9, 2012): no. http://dx.doi.org/10.1002/chin.201236234.

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4

Jamain, Zuhair, Melati Khairuddean, and Tay Guan-Seng. "Synthesis of New Star-Shaped Liquid Crystalline Cyclotriphosphazene Derivatives with Fire Retardancy Bearing Amide-Azo and Azo-Azo Linking Units." International Journal of Molecular Sciences 21, no. 12 (June 16, 2020): 4267. http://dx.doi.org/10.3390/ijms21124267.

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Two series of new hexasubstituted cyclotriphosphazene derivatives were successfully synthesized and characterized. These derivatives are differentiated by two types of linking units in the molecules such as amide-azo (6a–j) and azo-azo (8a–j). The homologues of the same series contain different terminal substituents such as heptyl, nonyl, decyl, dodecyl, tetradecyl, hydroxyl, carboxyl, chloro, nitro, and amino groups. All the intermediates and final compounds were characterized using Fourier transform infrared spectroscopy (FT-IR), nuclear magnetic resonance spectroscopy (NMR), and Carbon, Hydrogen, and Nitrogen (CHN) elemental analysis. Liquid crystal properties for all compounds were determined using polarized optical microscope (POM). It was found that only intermediates 2a–e with nitro and alkoxyl terminal chains showed a smectic A phase. All the final compounds with alkoxyl substituents are mesogenic with either smectic A or C phases. However, other intermediates and compounds were found to be non-mesogenic. The study on the fire retardancy of final compounds was determined using limiting oxygen index (LOI) method. The LOI value of pure polyester resin (22.53%) was increased up to 24.71% after treating with 1 wt% of hexachlorocyclotriphosphazene (HCCP). Moreover, all the compounds gave positive results on the LOI values and compound 6i with the nitro terminal substituent showed the highest LOI value of 27.54%.

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5

Cheon, Kap-Soo, Peter M. Kazmaier, Sam-Rok Keum, Kuk-Tae Park, and Erwin Buncel. "Azo-functionalized dendrimers." Canadian Journal of Chemistry 82, no. 4 (April 1, 2004): 551–66. http://dx.doi.org/10.1139/v04-009.

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We report the synthesis of azo-functionalized Starburst polyamidoamine (PAMAM) dendrimers. The following three systems of azo-functionalized PAMAM dendrimers were prepared by different synthetic routes: (i) phenylazo derivatives; (ii) naphthalimide azo derivatives; and (iii) phthalimide azo derivatives. Model compounds in each system were synthesized for spectroscopic comparison. Confirmation of structure was achieved using a combination of NMR and IR spectroscopy to ascertain the functional sites (i.e., the azo and the cyclic imides), while mass spectrometry and UVvis spectrophotometry were employed to ascertain the extent of functionalization. Substitution by the azo pendent groups increased the thermal stability of PAMAM dendrimers (TGA weight loss of the naphthalimide azo-functionalized PAMAM dendrimers up to 300 °C, ca. 5%).Key words: dendrimers, azo compounds, hydrazones, tautomerism, hydrogen bonding.

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6

Ali, Yousaf, Shafida Abd Hamid, and Umer Rashid. "Biomedical Applications of Aromatic Azo Compounds." Mini-Reviews in Medicinal Chemistry 18, no. 18 (October 12, 2018): 1548–58. http://dx.doi.org/10.2174/1389557518666180524113111.

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7

Klismeta, K., J. Teteris, and J. Aleksejeva. "Photoinduced mass transport in azo compounds." IOP Conference Series: Materials Science and Engineering 49 (December 13, 2013): 012036. http://dx.doi.org/10.1088/1757-899x/49/1/012036.

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8

Ungureanu, Eleonora-Mihaela, Alexandru C. Razus, Liviu Birzan, Mariana-Stefania Cretu, and George-Octavian Buica. "Electrochemical study of azo–azulene compounds." Electrochimica Acta 53, no. 24 (October 2008): 7089–99. http://dx.doi.org/10.1016/j.electacta.2008.04.087.

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9

MATSUI, M., S. KAWAMURA, K. SHIBATA, H. MURAMATSU, M. MITANI, H. SAWADA, and M. NAKAYAMA. "ChemInform Abstract: Perfluoroalkylation of Azo Compounds." ChemInform 24, no. 28 (August 20, 2010): no. http://dx.doi.org/10.1002/chin.199328132.

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10

Zhao, Meng-Yun, Yue-Feng Tang, and Guo-Zhi Han. "Recent Advances in the Synthesis of Aromatic Azo Compounds." Molecules 28, no. 18 (September 21, 2023): 6741. http://dx.doi.org/10.3390/molecules28186741.

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Aromatic azo compounds have -N=N- double bonds as well as a larger π electron conjugation system, which endows aromatic azo compounds with wide applications in the fields of functional materials. The properties of aromatic azo compounds are closely related to the substituents on their aromatic rings. However, traditional synthesis methods, such as the coupling of diazo salts, have a significant limitation with respect to the structural design of aromatic azo compounds. Therefore, many scientists have devoted their efforts to developing new synthetic methods. Moreover, recent advances in the synthesis of aromatic azo compounds have led to improvements in the design and preparation of light-response materials at the molecular level. This review summarizes the important synthetic progress of aromatic azo compounds in recent years, with an emphasis on the pioneering contribution of functional nanomaterials to the field.

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11

M. Ahmad, Shayma, Zahraa S. Al-Taie, Mohammed H. Al-Mashhadani, Rana A.Hammza, Mulia Rahmansyah, Muna Bufaroosha, and Emad Yousif. "An Overview of Preparation for Different Azo Compounds." Al-Nahrain Journal of Science 27, no. 1 (March 1, 2024): 1–13. http://dx.doi.org/10.22401/anjs.27.1.01.

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Azo compounds are a class of organic materials that have the group R-N=N-R' where the substitution group R and R' are aromatic or heterocyclic sides. The azo compounds have a variety of applications including dyes, pigments, and pharmaceuticals. The preparation and characterization of different azo compounds is an important area of research in organic synthesis. The azo compound synthesis typically involves the diazotization process for coupling between an aromatic amine and another aromatic compound containing an activating group such as -OH, -NH2, or -NR2. The reaction conditions must be carefully controlled to prevent side reactions, such as the formation of unwanted byproducts. Once synthesized, azo compounds can be characterized using a variety of techniques including UV-Vis spectroscopy, NMR spectroscopy, and mass spectrometry. UV-Vis spectroscopy is a commonly used technique for characterizing azo compounds. The absorption spectrum of an azo compound typically exhibits a strong absorption band in the visible region due to the delocalized π-electrons in the azo group. While in FTIR, the loss of the amine peak and showing a weak peak at about 1550 cm−1forthe (N=N) group, indicates the presence of Azo. The preparation and characterization of different azo compounds is a significant field of research in organic chemistry, which are applied as acid and base indicators, food coloring, optical switches, liquid crystal and in medicine. By carefully controlling the synthesis conditions and using a variety of characterization techniques, researchers can gain a better understanding of the properties and applications of these compounds.

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12

Mirkovic, Jelena, Gordana Uscumlic, Aleksandar Marinkovic, and Dusan Mijin. "Azo-hydrazone tautomerism of aryl azo pyridone dyes." Chemical Industry 67, no. 1 (2013): 1–15. http://dx.doi.org/10.2298/hemind120309053m.

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In the last three or four decades disperse dyes derived from pyridones (in particular azo pyridone dyes) have gained in importance, and are widely used in various fields. These compounds have excellent coloration properties, and are suitable for the dyeing of polyester fabrics. Basic features of these dyes are simplicity of their synthesis by diazotation and azo coupling. They generally have high molar extinction coefficient with medium to high light and wet fastness. The absorption maxima of these dyes show their visible absorption wavelength ranging from yellow to orange, which can be attributed to poorly delocalized electrons in the pyridone ring. However, there are several dyes with deep colors such as red or violet. Pyridone dyes with alkyl and aryl groups in ortho position to azo group show 2-pyridone/2-hydroxypyridine tautomerism, while those containing OH and NHR groups conjugated with the azo group show azo-hydrazone tautomerism. Determining azo-hydrazone tautomerism could be therefore interesting, since the tautomers have different physico-chemical properties and most importantly different coloration. The literature on azo-hydrazone tautomerism, determination of equilibrium position, and investigation of substituent and solvent influence on tautomerism has been summarized in the presented review. The general conclusion is that the equilibrium between two tautomers is influenced by the structure of the compounds and by the solvents used. The tautomeric behavior patterns of the arylazo pyridone dyes in the reviewed literature has been studied using various instrumental techniques, including FT-IR, UV-vis, and NMR spectroscopy. The quantum chemical calculations related to the azo-hydrazon tautomerism have also been included. A large number of pyridone dyes exist in hydrazone form in solid state, while in solvents there is a mixture of tautomers. In addition, the X-ray single-crystal diffraction data analysis of some commercial pyridone dyes has been discussed concluding that they all crystallize in the hydrazone form.

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13

Azeez, Hadi, Ahmed Al-kadhimi, and Nashwan Tapabashi. "Synthesis, Characterization and Biological Evaluation of Some Azo and Azo-Schiff Compounds." Kirkuk University Journal-Scientific Studies 14, no. 1 (March 28, 2019): 97–119. http://dx.doi.org/10.32894/kujss.2019.14.1.8.

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14

Ali, Wisam Hassan, Buthyna Abd el-hassan Naser, and Intisar Obaid Alfatlawi. "Coupling Compounds Behavior on Types of Fungi." American International Journal of Sciences and Engineering Research 2, no. 1 (January 25, 2019): 22–36. http://dx.doi.org/10.46545/aijser.v2i1.51.

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In our past work , some coupling azo- compounds were formatted characterized , chemical identification , which appeared good evidences for production our azo-coupling compounds , while in this paper , these azo-coupling derivatives were studied against types of fungi.

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15

Pakeeraiah, K., Sujit Kumar Mohanty, K. Eswar, and K. Raju. "Azo benzimidazole - A biologically active scaffold." International Journal of PharmTech Research 13, no. 3 (2020): 159–71. http://dx.doi.org/10.20902/ijptr.2019.130305.

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Azo compounds are a very unique class of chemical compounds, drawing considerations in scientific research. Azo compounds are studied as class of organic colorants which have at least a conjugated chromophore azo (-N=N-) group in fusion with one or more aromatic or heterocyclic ring system. Benzimidazole derivatives are privileged intermediates for the development of molecules of pharmaceutical or biological interest. Benzimidazole derivatives have gathered wide applications in diverse therapeutic areas such as antiulcer, anticancer agents, and anthelmintic species to name just a few. Although many azo derivatives of benzimidazole nucleus has been reported in literature but only few of them have been evaluated for their biological potencies. This review focuses primarily on those derivatives which are evaluated as anticancer, antibacterial, antifungal, antitubercular, and other medicinal agents. This review may be helpful for the investigators on the basis of substitution pattern on the nucleus with an objective to assist medicinal chemists for developing an SAR on azo benzimidazoles or similar compounds.

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16

Sridhara, M. B., G. R. Srinivasa, and D. Channe Gowda. "Ammonium chloride mediated reduction of azo compounds to hydrazo compounds." Journal of Chemical Research 2004, no. 1 (January 1, 2004): 74–75. http://dx.doi.org/10.3184/030823404323000873.

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17

Hamidian, Kourosh, Mohsen Irandoust, Ezzat Rafiee, and Mohammad Joshaghani. "Synthesis, Characterization, and Tautomeric Properties of Some Azo-azomethine Compounds." Zeitschrift für Naturforschung B 67, no. 2 (February 1, 2012): 159–64. http://dx.doi.org/10.1515/znb-2012-0208.

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The primary azo compound 1-(3-formyl-4-hydroxyphenylazo)-4-nitrobenzene reacts with some aliphatic and aromatic diamines and yields the corresponding azo-azomethine compounds. These compounds were characterized by elemental analysis, IR, UV/Vis, and NMR spectroscopy. The primary azo compound exists entirely in the azo form in solution as well as in the solid phase. The tautomeric structure of azo-azomethine compounds heavily depends on the solvent and the substituents. Aliphatic diamine-based compounds favor the enol-imine tautomer while aromatic diamine-based compounds have structures that lie between the two enol-imine and keto-amine tautomers due to a relatively strong intramolecular hydrogen bond. The compounds exhibit positive solvatochromism (bathochromic shift) so that their absorption bands move toward longer wavelengths as the polarity of the solvents increases. In addition, UV/Vis spectrophotometry has shown that the studied compounds have molar extinction coefficients larger than 40000.

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18

Akwi, Faith M., and Paul Watts. "The in situ generation and reactive quench of diazonium compounds in the synthesis of azo compounds in microreactors." Beilstein Journal of Organic Chemistry 12 (September 6, 2016): 1987–2004. http://dx.doi.org/10.3762/bjoc.12.186.

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In this paper, a micro-fluidic optimized process for the continuous flow synthesis of azo compounds is presented. The continuous flow synthesis of Sudan II azo dye was used as a model reaction for the study. At found optimal azo coupling reaction temperature and pH an investigation of the optimum flow rates of the reactants for the diazotization and azo coupling reactions in Little Things Factory-MS microreactors was performed. A conversion of 98% was achieved in approximately 2.4 minutes and a small library of azo compounds was thus generated under these reaction conditions from couplers with aminated or hydroxylated aromatic systems. The scaled up synthesis of these compounds in PTFE tubing (i.d. 1.5 mm) was also investigated, where good reaction conversions ranging between 66–91% were attained.

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19

KITAMURA, Akihide, Nobukazu MIYAGAWA, and Takashi KARATSU. "Photoinduced Electron-transfer Reaction of Azo Compounds." Journal of Synthetic Organic Chemistry, Japan 55, no. 8 (1997): 678–85. http://dx.doi.org/10.5059/yukigoseikyokaishi.55.678.

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20

Büyükgüngör, O., Ç. Albayrak, and M. Odabasoglu. "Spectroscopic investigation of some azo-azomethine compounds." Acta Crystallographica Section A Foundations of Crystallography 61, a1 (August 23, 2005): c315. http://dx.doi.org/10.1107/s0108767305086605.

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21

Du, Ke-Si, and Jing-Mei Huang. "Electrochemical dehydrogenation of hydrazines to azo compounds." Green Chemistry 21, no. 7 (2019): 1680–85. http://dx.doi.org/10.1039/c9gc00515c.

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A strategy for the electrochemical dehydrogenation of hydrazine compounds is disclosed under ambient conditions. Its synthetic value is well demonstrated by the highly efficient synthesis of symmetric and unsymmetric azo compounds. It is an environmentally friendly transformation and the present protocol was effective on a large scale.

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22

Matsui, Masaki, Yoshiyuki Iwata, Toshio Kato, and Katsuyoshi Shibata. "Reaction of aromatic azo compounds with ozone." Dyes and Pigments 9, no. 2 (January 1988): 109–17. http://dx.doi.org/10.1016/0143-7208(88)80010-x.

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23

Wagner-Wysiecka, Ewa, Natalia Łukasik, Jan F. Biernat, and Elżbieta Luboch. "Azo group(s) in selected macrocyclic compounds." Journal of Inclusion Phenomena and Macrocyclic Chemistry 90, no. 3-4 (January 8, 2018): 189–257. http://dx.doi.org/10.1007/s10847-017-0779-4.

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24

Orshulyak, O. O., and G. D. Levitskaya. "Voltammetric determination of zirconium using azo compounds." Journal of Analytical Chemistry 63, no. 3 (March 2008): 271–74. http://dx.doi.org/10.1134/s1061934808030143.

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25

Roldo, Marta, Eugen Barbu, James F. Brown, David W. Laight, John D. Smart, and John Tsibouklis. "Azo compounds in colon-specific drug delivery." Expert Opinion on Drug Delivery 4, no. 5 (September 2007): 547–60. http://dx.doi.org/10.1517/17425247.4.5.547.

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26

Rowe, F. M., and W. G. Dangerfield. "Decomposition of Azo Compounds by Mineral Acida." Journal of the Society of Dyers and Colourists 52, no. 2 (October 22, 2008): 48–57. http://dx.doi.org/10.1111/j.1478-4408.1936.tb01908.x.

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27

Pricelius, S., C. Held, M. Murkovic, M. Bozic, V. Kokol, A. Cavaco-Paulo, and G. M. Guebitz. "Enzymatic reduction of azo and indigoid compounds." Applied Microbiology and Biotechnology 77, no. 2 (September 22, 2007): 321–27. http://dx.doi.org/10.1007/s00253-007-1165-8.

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28

Velasco, Manuel I., Claudio O. Kinen, Rita Hoyos de Rossi, and Laura I. Rossi. "A green alternative to synthetize azo compounds." Dyes and Pigments 90, no. 3 (September 2011): 259–64. http://dx.doi.org/10.1016/j.dyepig.2010.12.009.

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29

McGowan, J. C., and T. Powell. "Rates of decompositions of certain AZO compounds." Recueil des Travaux Chimiques des Pays-Bas 81, no. 12 (September 2, 2010): 1061–67. http://dx.doi.org/10.1002/recl.19620811208.

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30

Bickel, A. F., and W. A. Waters. "The decomposition of aliphatic azo-compounds. I." Recueil des Travaux Chimiques des Pays-Bas 69, no. 3 (September 2, 2010): 312–20. http://dx.doi.org/10.1002/recl.19500690310.

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31

Bickel, A. F., and W. A. Waters. "The decomposition of aliphatic azo-compounds: II." Recueil des Travaux Chimiques des Pays-Bas 69, no. 12 (September 2, 2010): 1490–94. http://dx.doi.org/10.1002/recl.19500691204.

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32

Bevington, John C. "Initiation of polymerization: Azo compounds and peroxides." Makromolekulare Chemie. Macromolecular Symposia 10-11, no. 1 (October 1987): 89–107. http://dx.doi.org/10.1002/masy.19870100106.

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33

Liakou, S., M. Kornaros, and G. Lyberatos. "Pretreatment of azo dyes using ozone." Water Science and Technology 36, no. 2-3 (July 1, 1997): 155–63. http://dx.doi.org/10.2166/wst.1997.0508.

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Wastewaters produced in textile industrial processes contain organic dyes which are not easily amenable to biological treatment. Pretreatment with ozone is a promising method for oxidation of those dyes to more degradable compounds. The aim of this work is to assess the oxidation kinetics of a specific azo dye used in the textile industry, Orange II. Batch experiments were conducted in order to elucidate the oxidation route of the dye. Oxalate, formate and benzenesulfonate are found to be the oxidation intermediate compounds. A mathematical model which describes the dye elimination, the COD and BOD5 variation, the amount of ozone reacted and the time evolution of the intermediate compounds has been developed.

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34

Akram, Dana, Ismail A. Elhaty, and Shaikha S. AlNeyadi. "Synthesis and Antibacterial Activity of Rhodanine-Based Azo Dyes and Their Use as Spectrophotometric Chemosensor for Fe3+ Ions." Chemosensors 8, no. 1 (February 25, 2020): 16. http://dx.doi.org/10.3390/chemosensors8010016.

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This research includes the design and synthesis of new derivatives for rhodanine azo compounds (4a–c) containing a naphthalene ring. Physiochemical properties of the synthesized compounds were determined by their melting points, FTIR, 1H-NMR, 13C-NMR, and elemental analysis spectroscopic techniques. The biological activities of the newly prepared azo rhodanine compounds were evaluated against some pathogenic bacteria using three different bacterial species including (Escherichia coli., Pseudomonas aeruginosa, Staphylococcus aureus) and compared with amoxicillin as a reference drug. The results showed that our compounds have moderate-to-good vital activity against the mentioned pathogenic bacteria. The selectivity and sensitivity of the newly prepared rhodanine azo compounds with transition metals Co2+, Cu2+, Zn2+, Ni2+, and Fe3+ were studied using UV–vis and fluorescence spectroscopy techniques. Among the synthesized azos, azo 4c showed affinity toward Fe3+ ions with an association constant of 4.63 × 108 M−1. Furthermore, this azo showed high sensitivity toward Fe3+ ions with detection limits of 5.14 µM. The molar ratio and Benesi–Hildebrand methods confirmed the formation of complexes between azo 4c and Fe3+ with 1:2 binding stoichiometry. Therefore, azo 4c showed excellent potential for developing efficient Fe3+ chemosensors.

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35

Almashal, Faeza, Abeer Mohamed Jabar, and Adil Muala Dhumad. "Synthesis, characterization and DFT computational studies of new heterocyclic azo compounds." European Journal of Chemistry 9, no. 2 (June 30, 2018): 84–88. http://dx.doi.org/10.5155/eurjchem.9.2.84-88.1683.

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New heterocyclic azo compounds were prepared by coupling the diazonium salts with N-(4-methylphenyl)maleimide with various different sulfa compounds. The structure of heterocyclic azo compounds was determined by MS, FT-IR and 1H NMR techniques. The density function theory calculation at the B3LYP method with 6-311G(d,p) basis set is used to investigate the electronic structures of the prepared heterocyclic azo compounds. Mulliken charge distributions and HOMO-LUMO energies of the mentioned compounds have been also computed by same method and basis set.

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36

H�nig, Siegfried, and Michael Schmitt. "Azo bridges from azines. XV. Oxygenation of Unsaturated Cyclic Azo Compounds with peracids." Journal f�r Praktische Chemie/Chemiker-Zeitung 338, no. 1 (1996): 74–82. http://dx.doi.org/10.1002/prac.19963380113.

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37

Srinivasa, G. R., K. Abiraj, and D. Channe Gowda. "Facile Synthesis of Azo Compounds from Aromatic Nitro Compounds using Magnesium and Triethylammonium Formate." Australian Journal of Chemistry 57, no. 6 (2004): 609. http://dx.doi.org/10.1071/ch03143.

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Magnesium/triethylammonium formate is a convenient reagent for the reduction of aromatic nitro compounds to corresponding symmetrically substituted azo compounds. Various azo compounds containing additional reducible substituents, including halogen, nitrile, acid, phenol, ester, and methoxy functions, have been synthesized in a single step by the use of this reagent. The conversion is reasonably fast, clean, high yielding, and occurs at room temperature in methanol.

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38

Adu, Joseph Kwasi, Cedric Dzidzor Kodjo Amengor, Nurudeen Mohammed Ibrahim, Cynthia Amaning-Danquah, Charles Owusu Ansah, Dorcas Dzifa Gbadago, and Joseph Sarpong-Agyapong. "Synthesis and In Vitro Antimicrobial and Anthelminthic Evaluation of Naphtholic and Phenolic Azo Dyes." Journal of Tropical Medicine 2020 (June 1, 2020): 1–8. http://dx.doi.org/10.1155/2020/4850492.

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The antimicrobial activity of 2-naphtholic and phenolic azo compounds was determined against seven microbial species, Staphylococcus aureus (ATCC 25923), Streptococcus pyrogenes (clinical), and Enterococcus faecalis (ATCC 29212), Salmonella typhi (clinical), Pseudomonas aeruginosa (ATCC 27853), Escherichia coli (ATCC 251922), and Candida albicans (ATCC 10231), using the high-throughput spot culture growth inhibition assay (HT-SPOTi). The minimum inhibitory concentrations (MIC) were determined for the active azo dyes. All the azo compounds (A1–B4) were screened for anthelmintic activity against adult Ghanaian earthworms, Hyperiodrilus spp. As part of the systematic investigation for biological activity, all the azo compounds exhibited good antimicrobial activity against the seven human pathogenic microorganisms. All the compounds exhibited anthelminthic activity against adult Ghanaian earthworms, Hyperiodrilus spp.

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39

Luo, Chao, Oleg Borodin, Xiao Ji, Singyuk Hou, Karen J. Gaskell, Xiulin Fan, Ji Chen, et al. "Azo compounds as a family of organic electrode materials for alkali-ion batteries." Proceedings of the National Academy of Sciences 115, no. 9 (February 9, 2018): 2004–9. http://dx.doi.org/10.1073/pnas.1717892115.

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Organic compounds are desirable for sustainable Li-ion batteries (LIBs), but the poor cycle stability and low power density limit their large-scale application. Here we report a family of organic compounds containing azo group (N=N) for reversible lithiation/delithiation. Azobenzene-4,4′-dicarboxylic acid lithium salt (ADALS) with an azo group in the center of the conjugated structure is used as a model azo compound to investigate the electrochemical behaviors and reaction mechanism of azo compounds. In LIBs, ADALS can provide a capacity of 190 mAh g−1 at 0.5 C (corresponding to current density of 95 mA g−1) and still retain 90%, 71%, and 56% of the capacity when the current density is increased to 2 C, 10 C, and 20 C, respectively. Moreover, ADALS retains 89% of initial capacity after 5,000 cycles at 20 C with a slow capacity decay rate of 0.0023% per cycle, representing one of the best performances in all organic compounds. Superior electrochemical behavior of ADALS is also observed in Na-ion batteries, demonstrating that azo compounds are universal electrode materials for alkali-ion batteries. The highly reversible redox chemistry of azo compounds to alkali ions was confirmed by density-functional theory (DFT) calculations. It provides opportunities for developing sustainable batteries.

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40

Handajani, Juni, Urfa Tabtila, Nadia Rully Auliawati, and Abdul Rohman. "Characterization of buccal cell DNA after exposure to azo compounds: a cross-sectional study." F1000Research 9 (August 27, 2020): 1053. http://dx.doi.org/10.12688/f1000research.25798.1.

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Background: Azo compounds, containing naphthol and diazonium salts, are synthetic dyes widely used in the batik industry. Azo compounds are considered toxic when they are exposed to human tissue. The purpose of this study was to analyze buccal cell DNA exposed to azo compounds in batik workers. Methods: A cross-sectional study involving 20 male subjects divided into two groups (n=10 group), namely azo-exposed and non-exposed (control group). Inclusion criteria were batik workers of the colouring division who have been exposed to azo for at least 5 years. Buccal cells were taken using cytobrush then DNA were isolated from buccal cell. DNA isolation was done by buccal DNA kit, while the purity and concentration of the DNA was determined using spectrophotometer and electrophoresis. Results: The azo-exposed group revealed higher purity DNA than those in the control group. The purity of the DNA in the azo-exposed group and control group was 0.61±0.93 and 0.21±0.09, respectively, while the concentration of DNA was of 59.02 and 19.35 ng/UL, respectively. The ratio at 260/280 nm was 1.84-1.94 (azo-exposed) and 1.85-1.92 (control). Principal component analysis using the first principle component (PC1) and second principle component (PC2) could successfully classify subjects in the control and azo-exposed groups. Conclusion: Characteristics of DNA could be used as an indication of exposure to azo compounds in workers of batik industries.

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Handajani, Juni, Urfa Tabtila, Nadia Rully Auliawati, and Abdul Rohman. "Characterization of buccal cell DNA after exposure to azo compounds: a cross-sectional study." F1000Research 9 (September 18, 2020): 1053. http://dx.doi.org/10.12688/f1000research.25798.2.

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Abstract:

Background: Azo compounds, containing naphthol and diazonium salts, are synthetic dyes widely used in the batik industry. Azo compounds are considered toxic when they are exposed to human tissue. The purpose of this study was to analyze buccal cell DNA exposed to azo compounds in batik workers. Methods: A cross-sectional study involving 20 male subjects divided into two groups (n=10 group), namely azo-exposed and non-exposed (control group). Inclusion criteria were batik workers of the colouring division who have been exposed to azo for at least 5 years. Buccal cells were taken using cytobrush then DNA were isolated from buccal cell. DNA isolation was done by buccal DNA kit, while the purity and concentration of the DNA was determined using spectrophotometer and electrophoresis. Results: The azo-exposed group revealed higher purity DNA than those in the control group. The purity of the DNA in the azo-exposed group and control group was 0.61±0.93 and 0.21±0.09, respectively, while the concentration of DNA was of 59.02 and 19.35 ng/UL, respectively. The ratio at 260/280 nm was 1.84-1.94 (azo-exposed) and 1.85-1.92 (control). Principal component analysis using the first principle component (PC1) and second principle component (PC2) could successfully classify subjects in the control and azo-exposed groups. Conclusion: Characteristics of DNA could be used as an indication of exposure to azo compounds in workers of batik industries.

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Jiang, Bo, Yue-Yue Du, and Guo-Zhi Han. "Palladium-mediated base-free and solvent-free synthesis of aromatic azo compounds from anilines catalyzed by copper acetate." Green Processing and Synthesis 11, no. 1 (January 1, 2022): 823–29. http://dx.doi.org/10.1515/gps-2022-0070.

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Abstract Herein, we report a new one-step direct synthesis of aromatic azo compounds from anilines under mild conditions. With the catalysis of copper acetate mediated by palladium salt, rapid conversion of anilines to aromatic azo compounds can be observed under the conditions of base-free along with solvent-free. Furthermore, the cross-coupling nitridation reaction based on this strategy was also studied. This research provides not only a new way for the synthesis of symmetrical and asymmetrical aromatic azo compounds but also a strategy and platform for exploring catalytic applications of transition metal compounds.

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Abdallah, M., M. M. Alfakeer, N. F. Hasan, E. M. Mabrouk, and Ahmed M. Alharbi. "Polarographic Performance of Some Azo Derivatives Derived from 2-amino-4-hydroxy Pyridine and Its Inhibitory Effect on C-steel Corrosion in Hydrochloric acid." Oriental Journal of Chemistry 35, no. 1 (February 22, 2019): 98–109. http://dx.doi.org/10.13005/ojc/350111.

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The polarographic performance of five azo compounds derived from 2-amino-4-hydroxypyridine was studied in BR buffer series of pH 2-12. The polarograms of all azo compounds in strong acidic solutions gave a single irreversible diffusion-controlled 4-electron wave representing the splitting of the N=N group to the amine stage but in alkaline solutions 2-electron irreversible wave is obtained corresponding to the reduction of the azo center to the hydrazo stage. For NO2 substituted derivative, approximately two equal waves were observed in the acidic solutions, , but in the alkali, the rise of the second wave is approximately twice that of the first wave. The effect of substituents on electrode reaction was investigated and the kinetic parameters were calculated. The mechanistic pathway was proposed and interpreted. The dissociation constants of the tested azo compounds were examined by potentiometric methods and the M-L formation constants of their complexes with some transition metal ions were computed. Application of the investigated azo compounds as inhibitors of dissolution of carbon steel in in 1MHCl solutions was inspected using potentiodynamic polarization technique. The results indicated that these compounds inhibit C-steel corrosion in HCl solutions and the inhibition efficiency reached 81% in presence of 1x10-3 M of the inhibitors. The efficiency of the inhibitors follows the following sequence: III> II > I > IV > V This arrangement is consistent with the sequence of the E1/2 and the pka values of these azo compounds.

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Jun-Na, LIU, CHEN Zhi-Rong, and YUAN Shen-Feng. "Prediction of Visible Absorption of Pyridone Azo Compounds." Acta Physico-Chimica Sinica 21, no. 04 (2005): 402–7. http://dx.doi.org/10.3866/pku.whxb20050412.

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Yanagisawa, Akira, Takanori Koide, and Kazuhiro Yoshida. "Selective Propargylation of Azo Compounds with Barium Reagents." Synlett 2010, no. 10 (May 25, 2010): 1515–18. http://dx.doi.org/10.1055/s-0029-1219944.

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Yanagisawa, Akira, Toshiki Sawae, Seiya Yamafuji, Toshihiko Heima, and Kazuhiro Yoshida. "Reactive Barium-Promoted Benzylation of Diaryl Azo Compounds." Synlett 26, no. 08 (March 18, 2015): 1073–76. http://dx.doi.org/10.1055/s-0034-1380380.

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The Barbier-type benzylation of azo compounds with benzylic chlorides was achieved by using reactive barium as the promoter. Various benzylic hydrazines were synthesized from the corresponding benzylic chlorides. The thus-obtained benzylic hydrazines were further efficiently converted into benzylic amines by reductive N–N bond cleavage.

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Samanta, Subhas, Andrew A. Beharry, Oleg Sadovski, Theresa M. McCormick, Amirhossein Babalhavaeji, Vince Tropepe, and G. Andrew Woolley. "Photoswitching Azo Compounds in Vivo with Red Light." Journal of the American Chemical Society 135, no. 26 (June 21, 2013): 9777–84. http://dx.doi.org/10.1021/ja402220t.

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Boche, Gernot, Chris Meier, and Wolfgang Kleemiβ. "Hydrazines and azo compounds from O-diphenylphosphinoyl arylhydroxylamines." Tetrahedron Letters 29, no. 15 (January 1988): 1777–79. http://dx.doi.org/10.1016/s0040-4039(00)82041-9.

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Cui, Zhihua, Shufen Zhang, Jinzong Yang, and Lijun Tang. "Sulfonyl chlorination of sulfonate-containing naphthol azo compounds." Frontiers of Chemistry in China 3, no. 4 (August 16, 2008): 425–31. http://dx.doi.org/10.1007/s11458-008-0076-2.

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Kozak, G. D., A. Ya Vasin, and A. V. D’yachkova. "Estimating the explosion hazard of aromatic azo compounds." Combustion, Explosion, and Shock Waves 44, no. 5 (September 2008): 579–82. http://dx.doi.org/10.1007/s10573-008-0087-9.

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