Publication: 7-okso-3-(4-piridil) kumarin sübstitüentleri içeren ftalosiyaninlerin sentezi ve karakterizasyonu
Abstract
7-OKSO-3-(4-PİRİDİL) KUMARİN SÜBSTİTÜENTLERİ İÇEREN FTALOSİYANİNLERİN SENTEZİ VE KARAKTERİZASYONU Heteroatomik sistemler olan ftalosiyaninler, termal kararlılıkları, kimyasal dirençleri, elektriksel, optiksel veya sıvı-kristal özelliklerinden dolayı sadece teorik alanda değil, uygulama alanında da büyük öneme sahiptirler. Ftalosiyaninler boya ve pigment olarak kullanımlarının yanında kimyasal sensör, sıvı kristal, optik veri depolama, lazer yazıcıları ve foto dinamik terapi ile kanser tedavisi gibi birçok kullanım alanı için potansiyel bileşiklerdir. Sübstitüte olmuş kumarinlerin sentezleri, reaksiyonları ve biyolojik özellikleri modern heterosiklik kimyanın önemli bir parçası olmuştur. Kumarin bileşikleri antimikrobiyal, antimantar, antitümör, fotokemoterapi, antikanser, antikoagulant, anti-HIV gibi geniş bir spektrumda biyolojik aktivite göstermektedirler. Buna ilaveten, kumarinler yiyecek ve kozmetikte katkı maddesi olarak, optik parlatıcı ajanlar, lazer boyalarda geniş bir şekilde kullanılmaktadırlar. Deneysel çalışma sırasında önce 4-nitroftalonitril ve 3-nitroftalonitril sentezlenmiştir. Daha sonra Knovenagel kondenzasyonu ile 7-hidroksi-3-(4-piridil) kumarin sentezlenmiştir. Bu sentezlenen kumarin sırasıyla 4 ve 3-nitroftalonitril ile reaksiyona sokularak, 7-(3,4-disiyanofenoksi)-3-(4-piridil)kumarin ve 7-(2,3-disiyanofenoksi)-3-(4-piridil)kumarin elde edilmiştir. Daha sonra bu bileşikler üzerinden çinko (II) ve kobalt (II) metalli ftalosiyaninler sentezlendi. Sentezlenen kumarin türevi ftalosiyaninler çözünürlük farkından yararlanılarak, değişik çözücülerde ekstraksiyon işlemleri sonucu saflaştırıldılar. Sentezlemiş olduğumuz yeni 7-(3,4-disiyanofenoksi)-3-(4-piridil)kumarin, 7-(2,3-disiyanofenoksi)-3(4-piridil)kumarin ve kumarin türevli ftalosiyaninlerin yapıları UV-Visible, floresans, FT-IR, 1H-NMR spektrumları ile aydınlatılmıştır.
SYNTHESIS AND CHARACTERIZATION OF PHTHALOCYANINES CONTAINING 7-OXO-3-(4-PYRIDYL) COUMARIN SUBSTITUENTS The phthalocyanines which are heteroatomic systems due to their thermal and chemical stability, electrical, optical or liquid-crystal properties have considerable importance not only in theoretical field, but also in many different area of application. The synthesis, reactions and biological properties of substituted coumarins constitute a significant part of modern heterocyclic chemistry. Coumarin compounds display a broad spectrum of biological activities such as antimicrobial, antifungal, antitumor, photochemotherapy, anticancer, anticoagulant, anti-HIV. In addition, coumarins are widely used as additives in food and cosmetics, optically brightening agents and laser dyes. In experimental study, at first 4-nitrophthalonitrile and 3-nitrophthalonitrile were synthesized. Then 7-hydroxy-3-(4-pyridyl)coumarin was synthesized by Knoevenagel condensation reaction. Then these compound were treated with 4- and 3-nitrophthalonitrile respectively. 7-(3,4-dicyanophenoxy)-3-(4-pyridyl)coumarin and 7-(2,3-dicyanophenoxy)-3-(4-pyridyl)coumarin were obtained. Then, zinc (II) and cobalt (II) metallo phthalocyanines were synthesized from their precursor. The purification of these phthalocyanines with coumarin moieties were made by extraction with various solvent. The structure of new 7-(3,4-dicyanophenoxy)-3-(4-pyridyl)coumarin, 7-(2,3- dicyanophenoxy)-3-(4-pyridyl)coumarin and phthalocyanines with coumarin moieties were determined based on the results of spectroscopic methods such as UV-Visible, fluorescent, FT-IR, 1H-NMR.
SYNTHESIS AND CHARACTERIZATION OF PHTHALOCYANINES CONTAINING 7-OXO-3-(4-PYRIDYL) COUMARIN SUBSTITUENTS The phthalocyanines which are heteroatomic systems due to their thermal and chemical stability, electrical, optical or liquid-crystal properties have considerable importance not only in theoretical field, but also in many different area of application. The synthesis, reactions and biological properties of substituted coumarins constitute a significant part of modern heterocyclic chemistry. Coumarin compounds display a broad spectrum of biological activities such as antimicrobial, antifungal, antitumor, photochemotherapy, anticancer, anticoagulant, anti-HIV. In addition, coumarins are widely used as additives in food and cosmetics, optically brightening agents and laser dyes. In experimental study, at first 4-nitrophthalonitrile and 3-nitrophthalonitrile were synthesized. Then 7-hydroxy-3-(4-pyridyl)coumarin was synthesized by Knoevenagel condensation reaction. Then these compound were treated with 4- and 3-nitrophthalonitrile respectively. 7-(3,4-dicyanophenoxy)-3-(4-pyridyl)coumarin and 7-(2,3-dicyanophenoxy)-3-(4-pyridyl)coumarin were obtained. Then, zinc (II) and cobalt (II) metallo phthalocyanines were synthesized from their precursor. The purification of these phthalocyanines with coumarin moieties were made by extraction with various solvent. The structure of new 7-(3,4-dicyanophenoxy)-3-(4-pyridyl)coumarin, 7-(2,3- dicyanophenoxy)-3-(4-pyridyl)coumarin and phthalocyanines with coumarin moieties were determined based on the results of spectroscopic methods such as UV-Visible, fluorescent, FT-IR, 1H-NMR.