SYNTHESIS, STRUCTURE CHARACTERIZATION AND SOLVATOCHROMISM OF SOME ARYL AZO PYRIDONE DYES
Аутори
Matijević, BorkoMrđan, Gorana
Lađarević, Jelena
Valentić, Nataša
Mijin, Dušan
Mašulović, Aleksandra
Apostolov, Suzana
Vaštag, Đenđi
Конференцијски прилог (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
Aryl azo pyridone dyes belong to a very important class of organic compounds. World annual
production of synthetic dyes is over 60 % based on the azo derivatives. They are mostly used as
coloring agents for textiles, paper, leather, rubber, polymer, and many other materials. With the
development of high technology, these structures also found their application as components of
lasers and nonlinear optical systems, LCD (liquid crystal display) screens, and thermal printers.
Lately, increasing attention has been directed to the biological activity of azo compounds. It has
been proven that they have anti-tumor, anti-inflammatory, anti-oxidant, anti-microbial, and antituberculosis activity, while certain derivatives are used for therapeutic purposes. Aryl azo dyes
are widely used due to their excellent physicochemical properties (primarily high value of the
molar extinction coefficient and great resistance to light and wet processing) and the fact that
can be obtained in a simple ...method of diazotization and coupling. In this paper, three new dyes
of 6-hydroxy-5-(hydroxy substituted phenylazo)-4-methyl-2-oxo-1,2-dihydropyridine-3-
carbonitriles were synthesized by a diazo coupling reaction starting from aminophenols (2-, 3-
and 4-substituted) and 6-hydroxy-4-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile as coupling
components. The obtained dyes were characterized by melting point, IR, NMR, and UV-Vis
spectroscopy. Given the fact that the structure of the molecule and interactions obtained with the
surrounding medium can affect its activity, the possibility of azo hydrazo tautomerism has been
studied, as the influence of the position of the substituent present (orto-, meta- and para
position). In addition, the effect of the solvent used was determined by applying a solvatochromic
model using the LSER method (linear solvation energy relationship). Obtaining information
about the inter- and intramolecular relationships that newly synthesized compounds can achieve
may be of great importance for all further investigations and their potential application as
biologically active compounds.
Кључне речи:
Aryl azo pyridone dyes / carbonitrile / synthesis / azo-hydrazone tautomerism / solvatochromism / intermolecular interactionsИзвор:
Book of Abstracts / VIII International Congress "Engineering, Environment and Materials in Process Industry", Jahorina, March 20-23, 2023, 2023, 59-Издавач:
- Zvornik : Faculty of Technology
Колекције
Институција/група
Tehnološko-metalurški fakultetTY - CONF AU - Matijević, Borko AU - Mrđan, Gorana AU - Lađarević, Jelena AU - Valentić, Nataša AU - Mijin, Dušan AU - Mašulović, Aleksandra AU - Apostolov, Suzana AU - Vaštag, Đenđi PY - 2023 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/7308 AB - Aryl azo pyridone dyes belong to a very important class of organic compounds. World annual production of synthetic dyes is over 60 % based on the azo derivatives. They are mostly used as coloring agents for textiles, paper, leather, rubber, polymer, and many other materials. With the development of high technology, these structures also found their application as components of lasers and nonlinear optical systems, LCD (liquid crystal display) screens, and thermal printers. Lately, increasing attention has been directed to the biological activity of azo compounds. It has been proven that they have anti-tumor, anti-inflammatory, anti-oxidant, anti-microbial, and antituberculosis activity, while certain derivatives are used for therapeutic purposes. Aryl azo dyes are widely used due to their excellent physicochemical properties (primarily high value of the molar extinction coefficient and great resistance to light and wet processing) and the fact that can be obtained in a simple method of diazotization and coupling. In this paper, three new dyes of 6-hydroxy-5-(hydroxy substituted phenylazo)-4-methyl-2-oxo-1,2-dihydropyridine-3- carbonitriles were synthesized by a diazo coupling reaction starting from aminophenols (2-, 3- and 4-substituted) and 6-hydroxy-4-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile as coupling components. The obtained dyes were characterized by melting point, IR, NMR, and UV-Vis spectroscopy. Given the fact that the structure of the molecule and interactions obtained with the surrounding medium can affect its activity, the possibility of azo hydrazo tautomerism has been studied, as the influence of the position of the substituent present (orto-, meta- and para position). In addition, the effect of the solvent used was determined by applying a solvatochromic model using the LSER method (linear solvation energy relationship). Obtaining information about the inter- and intramolecular relationships that newly synthesized compounds can achieve may be of great importance for all further investigations and their potential application as biologically active compounds. PB - Zvornik : Faculty of Technology C3 - Book of Abstracts / VIII International Congress "Engineering, Environment and Materials in Process Industry", Jahorina, March 20-23, 2023 T1 - SYNTHESIS, STRUCTURE CHARACTERIZATION AND SOLVATOCHROMISM OF SOME ARYL AZO PYRIDONE DYES SP - 59 UR - https://hdl.handle.net/21.15107/rcub_technorep_7308 ER -
@conference{ author = "Matijević, Borko and Mrđan, Gorana and Lađarević, Jelena and Valentić, Nataša and Mijin, Dušan and Mašulović, Aleksandra and Apostolov, Suzana and Vaštag, Đenđi", year = "2023", abstract = "Aryl azo pyridone dyes belong to a very important class of organic compounds. World annual production of synthetic dyes is over 60 % based on the azo derivatives. They are mostly used as coloring agents for textiles, paper, leather, rubber, polymer, and many other materials. With the development of high technology, these structures also found their application as components of lasers and nonlinear optical systems, LCD (liquid crystal display) screens, and thermal printers. Lately, increasing attention has been directed to the biological activity of azo compounds. It has been proven that they have anti-tumor, anti-inflammatory, anti-oxidant, anti-microbial, and antituberculosis activity, while certain derivatives are used for therapeutic purposes. Aryl azo dyes are widely used due to their excellent physicochemical properties (primarily high value of the molar extinction coefficient and great resistance to light and wet processing) and the fact that can be obtained in a simple method of diazotization and coupling. In this paper, three new dyes of 6-hydroxy-5-(hydroxy substituted phenylazo)-4-methyl-2-oxo-1,2-dihydropyridine-3- carbonitriles were synthesized by a diazo coupling reaction starting from aminophenols (2-, 3- and 4-substituted) and 6-hydroxy-4-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile as coupling components. The obtained dyes were characterized by melting point, IR, NMR, and UV-Vis spectroscopy. Given the fact that the structure of the molecule and interactions obtained with the surrounding medium can affect its activity, the possibility of azo hydrazo tautomerism has been studied, as the influence of the position of the substituent present (orto-, meta- and para position). In addition, the effect of the solvent used was determined by applying a solvatochromic model using the LSER method (linear solvation energy relationship). Obtaining information about the inter- and intramolecular relationships that newly synthesized compounds can achieve may be of great importance for all further investigations and their potential application as biologically active compounds.", publisher = "Zvornik : Faculty of Technology", journal = "Book of Abstracts / VIII International Congress "Engineering, Environment and Materials in Process Industry", Jahorina, March 20-23, 2023", title = "SYNTHESIS, STRUCTURE CHARACTERIZATION AND SOLVATOCHROMISM OF SOME ARYL AZO PYRIDONE DYES", pages = "59", url = "https://hdl.handle.net/21.15107/rcub_technorep_7308" }
Matijević, B., Mrđan, G., Lađarević, J., Valentić, N., Mijin, D., Mašulović, A., Apostolov, S.,& Vaštag, Đ.. (2023). SYNTHESIS, STRUCTURE CHARACTERIZATION AND SOLVATOCHROMISM OF SOME ARYL AZO PYRIDONE DYES. in Book of Abstracts / VIII International Congress "Engineering, Environment and Materials in Process Industry", Jahorina, March 20-23, 2023 Zvornik : Faculty of Technology., 59. https://hdl.handle.net/21.15107/rcub_technorep_7308
Matijević B, Mrđan G, Lađarević J, Valentić N, Mijin D, Mašulović A, Apostolov S, Vaštag Đ. SYNTHESIS, STRUCTURE CHARACTERIZATION AND SOLVATOCHROMISM OF SOME ARYL AZO PYRIDONE DYES. in Book of Abstracts / VIII International Congress "Engineering, Environment and Materials in Process Industry", Jahorina, March 20-23, 2023. 2023;:59. https://hdl.handle.net/21.15107/rcub_technorep_7308 .
Matijević, Borko, Mrđan, Gorana, Lađarević, Jelena, Valentić, Nataša, Mijin, Dušan, Mašulović, Aleksandra, Apostolov, Suzana, Vaštag, Đenđi, "SYNTHESIS, STRUCTURE CHARACTERIZATION AND SOLVATOCHROMISM OF SOME ARYL AZO PYRIDONE DYES" in Book of Abstracts / VIII International Congress "Engineering, Environment and Materials in Process Industry", Jahorina, March 20-23, 2023 (2023):59, https://hdl.handle.net/21.15107/rcub_technorep_7308 .