Year 2020, Volume 15 , Issue 2, Pages 319 - 329 2020-11-29

Novel Heterocyclic Azo Compounds: Synthesis, Characterization and DFT Calculations
Yeni Heterosiklik Azo Bileşikler: Sentez, Karakterizasyon ve DFT Hesaplamaları

Shahodat IRMUMINOVA [1] , Barış SEZGİN [2] , Tahir TİLKİ [3]


Today, it is of great importance to synthesize new azo compounds as well as to conduct research in different areas of use. More than one usage area is increasing day by day in high-tech products (laser printing materials, printer toners, liquid crystals, etc.) as well as in many sectors such as paper, food, cosmetics, textile and leather. In this study, considering these advantages, the compounds of 3-amino-1H-pyrazol-5-ol, 1H-1,2,4-triazol-3-amine, 3-amino-1H-phenyl-5-ol were used as starting materials. As a result of azo coupling of diazonium salts with resorcinol and 3,5-dihydroxy benzoic acid, new azo compounds were synthesized, their structures were characterized by spectroscopic methods such as FT-IR and 1H-NMR, and different solvent effects on visible absorption spectra were investigated. Molecular geometry and vibration frequency calculations of synthesized compounds were made with Density Functional Theory (DFT) using 6-311G (d,p) basis set and B3LYP level. Additional, electronic properties and HOMO-LUMO orbital calculations were carried out with time dependent DFT (TD-DFT) approach. As a result of this study, it has been observed that azo compounds containing heterocyclic amine groups have batchromic effects and bright colors. It is anticipated that this study will make important contributions to the literature and the dyestuff industry and will form a basis for potential applications.
Günümüzde yeni azo bileşikleri sentezlemek ile birlikte farklı kullanım alanlarında da araştırma yapmak büyük önem taşımaktadır. Kâğıt, gıda, kozmetik, tekstil ve deri gibi birçok sektörde kullanım alanları olduğu gibi yüksek teknoloji ürünlerinde de (lazer baskı materyelleri, yazıcı tonerleri, sıvı kristaller vb.) birden fazla kullanım alanı her geçen gün giderek artmaktadır. Bu çalışmada, bu avantajlar göz önünde bulundurarak, başlangıç maddeleri olarak 3-amino-1H-pirazol-5-ol, 1H-1,2,4-triazol-3-amin, 3-amino-1H-fenil-5-ol bileşiklerinin diazonyum tuzlarının resorsinol ve 3,5-dihidroksi benzoik asitle azo kenetlenmesi sonucu yeni azo bileşikleri sentezlenerek, yapıları FT-IR, 1H-NMR gibi spektroskopik yöntemlerle karakterize edilmiş ve görünür bölge absorpsiyon spektrumları üzerine farklı çözücü etkisi araştırılmıştır. Sentezlenen moleküllerin moleküler geometrisi hesaplamaları, 6-311G (d,p) temel seti ile B3LYP seviyesi kullanılarak Yoğunluk Fonksiyonel Teorisi (DFT) ile yapılmıştır. Ayrıca HOMO-LUMO orbital hesaplamaları zamana bağlı DFT (TD-DFT) yaklaşımı ile gerçekleştirilmiştir. Yapılmış olan bu çalışma sonucunda heterosiklik amin grubu içeren azo bileşiklerinin batokromik etkiye ve parlak renklere sahip olduğu gözlemlenmiştir. Bu çalışma, literatüre ve boyarmadde endüstrisine önemli katkılar sağlayacağı ve potansiyel uygulamalara temel oluşturacağı öngörülmektedir.
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Primary Language en
Subjects Engineering, Chemical
Journal Section Makaleler
Authors

Orcid: 0000-0001-6896-4197
Author: Shahodat IRMUMINOVA
Institution: SÜLEYMAN DEMİREL ÜNİVERSİTESİ
Country: Turkey


Orcid: 0000-0001-5359-4488
Author: Barış SEZGİN (Primary Author)
Institution: SÜLEYMAN DEMİREL ÜNİVERSİTESİ
Country: Turkey


Orcid: 0000-0002-1040-2375
Author: Tahir TİLKİ
Institution: SÜLEYMAN DEMİREL ÜNİVERSİTESİ
Country: Turkey


Supporting Institution Süleyman Demirel Üniversitesi Bilimsel Araştırma Projeleri Koordinasyon Birimi
Project Number FYL-2019-7399
Thanks Bu çalışmanın gerçekleştirilmesi için gerekli finansal destekleri için SDÜ-BAP (FYL-2019-7399) birimine teşekkür ederiz.
Dates

Publication Date : November 29, 2020

Bibtex @research article { sdufeffd820455, journal = {Süleyman Demirel Üniversitesi Fen Edebiyat Fakültesi Fen Dergisi}, issn = {}, eissn = {1306-7575}, address = {}, publisher = {Süleyman Demirel University}, year = {2020}, volume = {15}, pages = {319 - 329}, doi = {10.29233/sdufeffd.820455}, title = {Novel Heterocyclic Azo Compounds: Synthesis, Characterization and DFT Calculations}, key = {cite}, author = {Irmumınova, Shahodat and Sezgi̇n, Barış and Ti̇lki̇, Tahir} }
APA Irmumınova, S , Sezgi̇n, B , Ti̇lki̇, T . (2020). Novel Heterocyclic Azo Compounds: Synthesis, Characterization and DFT Calculations . Süleyman Demirel Üniversitesi Fen Edebiyat Fakültesi Fen Dergisi , 15 (2) , 319-329 . DOI: 10.29233/sdufeffd.820455
MLA Irmumınova, S , Sezgi̇n, B , Ti̇lki̇, T . "Novel Heterocyclic Azo Compounds: Synthesis, Characterization and DFT Calculations" . Süleyman Demirel Üniversitesi Fen Edebiyat Fakültesi Fen Dergisi 15 (2020 ): 319-329 <https://dergipark.org.tr/en/pub/sdufeffd/issue/57875/820455>
Chicago Irmumınova, S , Sezgi̇n, B , Ti̇lki̇, T . "Novel Heterocyclic Azo Compounds: Synthesis, Characterization and DFT Calculations". Süleyman Demirel Üniversitesi Fen Edebiyat Fakültesi Fen Dergisi 15 (2020 ): 319-329
RIS TY - JOUR T1 - Novel Heterocyclic Azo Compounds: Synthesis, Characterization and DFT Calculations AU - Shahodat Irmumınova , Barış Sezgi̇n , Tahir Ti̇lki̇ Y1 - 2020 PY - 2020 N1 - doi: 10.29233/sdufeffd.820455 DO - 10.29233/sdufeffd.820455 T2 - Süleyman Demirel Üniversitesi Fen Edebiyat Fakültesi Fen Dergisi JF - Journal JO - JOR SP - 319 EP - 329 VL - 15 IS - 2 SN - -1306-7575 M3 - doi: 10.29233/sdufeffd.820455 UR - https://doi.org/10.29233/sdufeffd.820455 Y2 - 2020 ER -
EndNote %0 Süleyman Demirel Üniversitesi Fen Edebiyat Fakültesi Fen Dergisi Novel Heterocyclic Azo Compounds: Synthesis, Characterization and DFT Calculations %A Shahodat Irmumınova , Barış Sezgi̇n , Tahir Ti̇lki̇ %T Novel Heterocyclic Azo Compounds: Synthesis, Characterization and DFT Calculations %D 2020 %J Süleyman Demirel Üniversitesi Fen Edebiyat Fakültesi Fen Dergisi %P -1306-7575 %V 15 %N 2 %R doi: 10.29233/sdufeffd.820455 %U 10.29233/sdufeffd.820455
ISNAD Irmumınova, Shahodat , Sezgi̇n, Barış , Ti̇lki̇, Tahir . "Novel Heterocyclic Azo Compounds: Synthesis, Characterization and DFT Calculations". Süleyman Demirel Üniversitesi Fen Edebiyat Fakültesi Fen Dergisi 15 / 2 (November 2020): 319-329 . https://doi.org/10.29233/sdufeffd.820455
AMA Irmumınova S , Sezgi̇n B , Ti̇lki̇ T . Novel Heterocyclic Azo Compounds: Synthesis, Characterization and DFT Calculations. Süleyman Demirel Üniversitesi Fen Edebiyat Fakültesi Fen Dergisi. 2020; 15(2): 319-329.
Vancouver Irmumınova S , Sezgi̇n B , Ti̇lki̇ T . Novel Heterocyclic Azo Compounds: Synthesis, Characterization and DFT Calculations. Süleyman Demirel Üniversitesi Fen Edebiyat Fakültesi Fen Dergisi. 2020; 15(2): 319-329.
IEEE S. Irmumınova , B. Sezgi̇n and T. Ti̇lki̇ , "Novel Heterocyclic Azo Compounds: Synthesis, Characterization and DFT Calculations", Süleyman Demirel Üniversitesi Fen Edebiyat Fakültesi Fen Dergisi, vol. 15, no. 2, pp. 319-329, Nov. 2020, doi:10.29233/sdufeffd.820455