Publication: 7-Oksi-3-[3,5-BİS(Triflorometil)Fenil] Kumarin içeren Metalli Ftalosiyaninlerin sentezi ve karakterizasyonu
Abstract
7-OKSİ-3-[3,5-BİS(TRİFLOROMETİL)FENİL]KUMARİN İÇEREN METALLİ FTALOSİYANİNLERİN SENTEZİ VE KARAKTERİZASYONU Bu çalışmada sentezlenen ftalosiyanin bileşikleri kumarin türevi içermektedir. Kumarin (2H-1-benzopiran-2-on) tonka fasulyesi, karanfil ve lavanta çiçeği içeren temel yağlar ve yüksek bitkilerin çoğunun yapısında vardır. Bazı türevleri, kumarinlerin çeşitli biyolojik aktiviteleri antikoagulantlar, yiyecek ve kozmetikte katkı maddeleri, böcek ilaçlarının hazırlanmasında, optik parlatıcılar ve flouresans yayan lazer boyalar olarak kullanılır. Kumarinlerin farklı biyolojik aktiviteleri, antikoagülant, antitrombotik, antimikorbiyal, antikanser ve anti-HIV olarak bilinir. Ftalosiyanin ilk olarak 1907 yılında Braun ve Tcherniac tarafından yüksek sıcaklıkta ftalimid ve asetik anhidritten o-siyano benzamid sentezlenmesi sırasında yan ürün olarak elde edilmiştir. Ftalosiyaninler genellikle yüksek sıcaklıklarda sentezlenirler. Ftalosiyaninler ısıya, ışığa ve asitlere karşı dayanıklılıklarına rağmen düşük çözünürlüğe sahiptirler. Ftalosiyaninlerin çözünürlükleri, farklı zincir uzunluklarında ya da dallanmış alkil ya da alkoksi grupları gibi sübstitüentlerin yapıya eklenmesiyle arttırılabilmektedir. Böylece farklı yapıda çözünür ftalosiyaninler sentezlenmektedir. Bu çalışmada, öncelikle 3-nitroftalonitril ve 4-nitroftalonitril bileşikleri literatüre göre sentezlenmiştir. Sentezlenmiş olan 7-hidroksi-3-[3,5-bis(trifloro metil)fenil]kumarin ile 4- nitroftalonitril ve 3- nitroftalonitril bileşikleri ayrı ayrı reaksiyona sokularak; sırasıyla 7-(3,4-disiyanofenoksi)-3-[3,5-bis(triflorometil)fenil] kumarin ve 7-(2,3-disiyanofenoksi)-3-[3,5- bis(triflorometil) fenil]kumarin sentezlenmiştir. Bu bileşikler ile çinko (II), kobalt (II), nikel (II) ve bakır (II) ftalosiyanin kompleksleri (M: Zn, Co, Ni, Cu) sentezlenmiştir. Sentezlenen ftalosiyanin bileşikleri, çeşitli organik çözücülerle yıkanmış ve kolon kromatografisi yöntemiyle saflaştırılmıştır. Yeni sentezlenen bileşiklerin karakterizasyonu IR, UV-Vis ve Kütle spektrumlarıyla yapılmıştır.
SYNTHESIS AND CHARACTERIZATION OF METALLO PHTHALOCYANINES BEARING 7-OXY-3-[3,5-BİS(TRİFLOUROMETHYL)PHENYL]COUMARİN In this study, synthesized phthalocyanine compounds bears a coumarin derivative. Coumarin (2H-1-benzopyran-2-one) is a constituent of many higher plants and essential oils, including tonka beans, sweet clover and lavender. Some derivatives are used as anticoagulants, additives in food and cosmetics, in the preparation of insecticides, optical brighteners and dispersed fluorescent, laser dyes. The diverse biological activities of coumarins are well known as anticoagulant, antithrombotic, antimicrobial, antibacterial, anticancer and anti-HIV activities. The first synthesis of phthalocyanines was reported by Braun and Tcherniac in 1907 during o-cyanobenzamide synthesis from phthalimid and acetic anhydride in high temperature, phthalocyanines were obtained as a by coproduct. Generally phthalocyanine can be performed synthesis in high temperature. Although phthalocyanines have strength against heat, light and acid, their solubility are highly low. Their solubility can be improved by the incorporation of substituents, such as alkyl or alkoxy groups of different chain lenghts, or branched systems. Thus different soluble phthalocyanines can be synthesized. In experimental study, at first 4-nitrophthalonitrile and 3-nitrophthalonitrile were synthesized according to the known literature. Then the 7-hydroxy-3-[3,5-bis(triflouromethyl)phenyl]coumarin compound which was synthesized by Knoevenagel reaction treated with 4- and 3-nitrophthalonitrile respectively 7-(3,4-dicyanophenoxy)-3-[3,5-bis(triflourometyl)phenyl]coumarin and 7-(2,3-dicyanophenoxy)-3-[3,5-bis(triflourometyl)phenyl]coumarin were obtained. Zinc (II), cobalt (II), nickel (II) and copper (II) phthalocyanine complexes were synthesized from these compounds. The compounds obtained were purified by washing with various solvents and using silica gel column chromatography. Novel compounds were characterized by UV-Vis, FT-IR and Mass spectroscopy.
SYNTHESIS AND CHARACTERIZATION OF METALLO PHTHALOCYANINES BEARING 7-OXY-3-[3,5-BİS(TRİFLOUROMETHYL)PHENYL]COUMARİN In this study, synthesized phthalocyanine compounds bears a coumarin derivative. Coumarin (2H-1-benzopyran-2-one) is a constituent of many higher plants and essential oils, including tonka beans, sweet clover and lavender. Some derivatives are used as anticoagulants, additives in food and cosmetics, in the preparation of insecticides, optical brighteners and dispersed fluorescent, laser dyes. The diverse biological activities of coumarins are well known as anticoagulant, antithrombotic, antimicrobial, antibacterial, anticancer and anti-HIV activities. The first synthesis of phthalocyanines was reported by Braun and Tcherniac in 1907 during o-cyanobenzamide synthesis from phthalimid and acetic anhydride in high temperature, phthalocyanines were obtained as a by coproduct. Generally phthalocyanine can be performed synthesis in high temperature. Although phthalocyanines have strength against heat, light and acid, their solubility are highly low. Their solubility can be improved by the incorporation of substituents, such as alkyl or alkoxy groups of different chain lenghts, or branched systems. Thus different soluble phthalocyanines can be synthesized. In experimental study, at first 4-nitrophthalonitrile and 3-nitrophthalonitrile were synthesized according to the known literature. Then the 7-hydroxy-3-[3,5-bis(triflouromethyl)phenyl]coumarin compound which was synthesized by Knoevenagel reaction treated with 4- and 3-nitrophthalonitrile respectively 7-(3,4-dicyanophenoxy)-3-[3,5-bis(triflourometyl)phenyl]coumarin and 7-(2,3-dicyanophenoxy)-3-[3,5-bis(triflourometyl)phenyl]coumarin were obtained. Zinc (II), cobalt (II), nickel (II) and copper (II) phthalocyanine complexes were synthesized from these compounds. The compounds obtained were purified by washing with various solvents and using silica gel column chromatography. Novel compounds were characterized by UV-Vis, FT-IR and Mass spectroscopy.