Publication: 3-fenoksiasetik asit sübstitue ftalosiyaninlerin sentezi ve ürünlerin karakterizasyonu
Abstract
3-FENOKSİASETİK ASİT SÜBSTİTUE FTALOSİYANİNLERİN SENTEZİ VE ÜRÜNLERİN KARAKTERİZASYONU Koordinasyon bileşiklerinin önemli bir sınıfı olan ftalosiyaninler, pigment, katalizör, kimyasal sensör gibi birçok alanda kullanılır. Ftalosiyaninler ısıya, ışığa, asitlere ve bazlara karşı oldukça dayanıklıdırlar. Ancak sübstitue grup içermediklerinden organik çözücülerde çözünmezler. Ftalosiyanin yapısının periferal pozisyonlarında uygun fonksiyonel grupların bulunmasıyla protik veya aprotik çözücülerdeki çözünürlüğü arttırılabilir. Bu çalışmada 3-fenoksiasetik asit grupları içeren metalli ftalosiyaninler sentezlenmiştir ve yapıları aydınlatılmıştır. İlk olarak 3-nitroftalonitril ve 4-nitroftalonitril bileşikleri literatüre göre sentezlenmiştir. Bu bileşiklerden m-(2,3-disiyanofenoksi)fenilasetikasit ve m-(3,4-disiyanofenoksi)fenilasetikasit bileşikleri sentezlendi. Bu bileşiklerin çeşitli metal tuzlarıyla reaksiyonundan karboksilik asit grupları içeren metalli ftalosiyaninler sentezlendi. Bu ftalosiyaninlerin tiyonil klorür ile reaksiyonuyla asit klorürler elde edildi. Asit klorürlerin piridin içinde hekzanol ile reaksiyonundan ester grupları içeren metalli ftalosiyaninler sentezlendi ve kolon kromotografisiyle saflaştırıldı. Asit klorürlerin THF içinde hekzil amin ile reaksiyonundan ise amid grupları içeren metalli ftalosiyaninler sentezlendi ve çeşitli organik çözücülerde yıkanarak saflaştırıldı. Sentezlenen bileşiklerin karakterizasyonu UV/ Vis, FT-IR, 1H-NMR spektroskopisi ile yapıldı.
SYNTHESIS OF PHTHALOCYANINES SUBSTITUTED WİTH 3-PHENYLOXYACETIC ACID AND CHARACTERIZATION OF PRODUCTS Phthalocyanines are used in many fields such as pigments, chemical sensors, catalysts which is an important class of coordination compounds. Phthalocyanines have quite strength against heat, light, acids and bases. However, they do not contain substituted groups are insoluble in organic solvents. It has been found that suitable functional groups in the peripheral position of the phthalocyanine structure can improve the solubility in protic or nonprotic solvents. In this study, the synthesis of metallo phthalocyanines containing 3-phenyloxyacetic acid were performed. The structures of these compounds were determined. First, 3-nitrophthalonitrile and 4-nitrophthalonitrile were synthesized according to the known literature. m-(2,3-Dicyanophenoxy)phenylaceticacid and m-(3,4-dicyanophenoxy)phenylaceticacid were synthesized in these compounds. Metallophthalocyanines containing carboxylic acid groups were performed by reaction several metal salts of these compounds. Acid chlorides occur by reaction of this phthalocyanines and thionyl chlorides. Phthalocyanines containing ester moieties were synthesized by reaction of hexanol and acid chlorides in pyridine and this compound was purified with silica gel column chromatography. Phthalocyanines containing amide moieties were synthesized by reaction of hexylamines and acid chlorides in THF and these compounds were purified by washing with various solvents. Characterization of these compounds involved a combination of methods including UV/ Vis, FT-IR, 1H-NMR spectroscopy.
SYNTHESIS OF PHTHALOCYANINES SUBSTITUTED WİTH 3-PHENYLOXYACETIC ACID AND CHARACTERIZATION OF PRODUCTS Phthalocyanines are used in many fields such as pigments, chemical sensors, catalysts which is an important class of coordination compounds. Phthalocyanines have quite strength against heat, light, acids and bases. However, they do not contain substituted groups are insoluble in organic solvents. It has been found that suitable functional groups in the peripheral position of the phthalocyanine structure can improve the solubility in protic or nonprotic solvents. In this study, the synthesis of metallo phthalocyanines containing 3-phenyloxyacetic acid were performed. The structures of these compounds were determined. First, 3-nitrophthalonitrile and 4-nitrophthalonitrile were synthesized according to the known literature. m-(2,3-Dicyanophenoxy)phenylaceticacid and m-(3,4-dicyanophenoxy)phenylaceticacid were synthesized in these compounds. Metallophthalocyanines containing carboxylic acid groups were performed by reaction several metal salts of these compounds. Acid chlorides occur by reaction of this phthalocyanines and thionyl chlorides. Phthalocyanines containing ester moieties were synthesized by reaction of hexanol and acid chlorides in pyridine and this compound was purified with silica gel column chromatography. Phthalocyanines containing amide moieties were synthesized by reaction of hexylamines and acid chlorides in THF and these compounds were purified by washing with various solvents. Characterization of these compounds involved a combination of methods including UV/ Vis, FT-IR, 1H-NMR spectroscopy.