Publication: Karboksilik asit ve/ veya 2H-1-Benzopiran-2-On türevi bazı Ftalosiyaninlerin sentezi ve karakterizasyonu
Abstract
KARBOKSİLİK ASİT VE/ VEYA 2H-1-BENZOPİRAN-2-ON TÜREVİ BAZI FTALOSİYANİNLERİN SENTEZİ VE KARAKTERİZASYONU Kumarin (2H-1-benzopiran-2-on) ve türevleri, biyolojik, tıbbi aktivitelerinin yanı sıra termal kararlılık ve optik özelliklere sahip olmaları nedeniyle organik bileşiklerin önemli bir sınıfını oluştururlar. Harika mavi ve yeşil boyar madde olan ftalosiyaninler yüksek fiziksel ve kimyasal kararlılığa sahip sentetik bileşiklerdir. Ftalosiyaninler optik, elektriksel ve katalitik uygulamalarda, kanser tedavisi ve diğer medikal uygulamalarda kullanılmaktadırlar. Bu çalışma kapsamında, 6-hekziloksi-3-[p-(3',4'-disiyanofenoksi)fenil]-kumarin, 8-hekziloksi-3-[p-(3',4'-disiyanofenoksi)fenil]kumarin, 7,8-dihekziloksi-3-[p-(3',4'-disiyanofenoksi)fenil]kumarin ve 7,8-dihekziloksi-3-[p-(2',3'-disiyano-fenoksi)fenil]kumarin bileşikleri ve bu bileşiklerden de metalsiz ve metalli (M: Zn, Co) ftalosiyanin kompleksleri sentezlendi. 7,8-Dihidroksi-3-[p-(3',4'-disiyanofenoksi)fenil]kumarin ve 7,8-dihidroksi-3-[p-(2',3'-disiyanofenoksi)fenil]-kumarin’in 4- ve 5- oksijen atomu içeren taç eter türevleri sentezlenerek ilk kez kumarin türevi taç eterleri içeren yeni ftalosiyaninler elde edildi. Ayrıca 4-kloro-5-(4-feniloksiasetik asit)ftalonitril, 4,5-bis(feniloksiasetik asit)ftalonitril ve 4-hekziltiyo-5-(4-feniloksiasetik asit)ftalonitril bileşikleri sentezlendi ve bu bileşikler kullanılarak suda çözünür yeni ftalosiyaninler elde edildi. 4,5-Bis[7-hekziloksi-3-(4-oksifenil)kumarin]ftalonitril bileşiği ve bu bileşikten de periferal pozisyonda sekiz adet kumarin bulunduran çinko metalli ftalosiyanin sentezlendi. Elde edilen yeni bileşiklerin yapıları FT-IR, UV/ Vis, 1H-NMR ve MALDI-TOF kütle spektroskopisi yöntemleri ile aydınlatıldı. Floresans spektroskopisi ile ölçümler yapılarak elde edilen bileşiklerin floresans özellikleri incelendi.
SYNTHESIS AND CHARACTERIZATION OF CARBOXYLIC ACID AND/ OR 2H-1-BENZOPYRAN-2-ONE DERIVATIVES OF SOME PHTHALOCYANINES Coumarin (2H-1-benzopyran-2-one) and their derivatives are an important class of organic compounds, which exhibit not only excellent biological and medical activities but also have thermal stability and optical properties. Phthalocyanines (Pcs) are blue-green coloured synthetic compounds with high chemical and physical stability. They have been used in optical, electrical, and catalytic applications, photodynamic reagents for cancer therapy and for other medical applications. In this study, novel phthalocyanines were obtained using 6-hexyloxy-3-[p-(3',4'-dicyanophenoxy)phenyl]coumarin, 8-hexyloxy-3-[p-(3',4'-dicyanophenoxy)-phenyl]coumarin, 7,8-dihexyloxy-3-[p-(3',4'-dicyanophenoxy)phenyl]coumarin and 7,8-dihexyloxy-3-[p-(2',3'-dicyanophenoxy)phenyl]coumarin compounds. Phthalocyanine-coumarin-crown ether complexes were sytnhesized using 7,8-(12-crown-4)-3-[p-(3,4-dicyanophenoxy)phenyl]coumarin, 7,8-(12-crown-4)-3-[p-(2,3-dicyanophenoxy)phenyl]coumarin, 7,8-(15-crown-5)-3-[p-(3,4-dicyano-phenoxy)phenyl]coumarin and 7,8-(15-crown-5)-3-[p-(2,3-dicyanophenoxy)-phenyl]coumarin compounds. Also novel water soluble phthalocyanines were obtained from 4-chloro-5-(4-phenyloxyacetic acid)phthalonitrile, 4,5-bis(phenyloxyacetic acid)phthalonitrile and 4-hexylthio-5-(4-phenyloxyacetic acid)phthalonitrile compounds. Zinc metallo phthalocyanine bearing eight coumarins at peripheral positions was synthesized from 4,5-bis[7-hexyloxy-3-(4-oxyphenyl)coumarin]phthalonitrile. The structure of new compounds were determined based on the results of spectroscopic methods such as FT-IR, UV/ Vis, 1H-NMR ve MALDI-TOF. Their fluorescence properties were investigated.
SYNTHESIS AND CHARACTERIZATION OF CARBOXYLIC ACID AND/ OR 2H-1-BENZOPYRAN-2-ONE DERIVATIVES OF SOME PHTHALOCYANINES Coumarin (2H-1-benzopyran-2-one) and their derivatives are an important class of organic compounds, which exhibit not only excellent biological and medical activities but also have thermal stability and optical properties. Phthalocyanines (Pcs) are blue-green coloured synthetic compounds with high chemical and physical stability. They have been used in optical, electrical, and catalytic applications, photodynamic reagents for cancer therapy and for other medical applications. In this study, novel phthalocyanines were obtained using 6-hexyloxy-3-[p-(3',4'-dicyanophenoxy)phenyl]coumarin, 8-hexyloxy-3-[p-(3',4'-dicyanophenoxy)-phenyl]coumarin, 7,8-dihexyloxy-3-[p-(3',4'-dicyanophenoxy)phenyl]coumarin and 7,8-dihexyloxy-3-[p-(2',3'-dicyanophenoxy)phenyl]coumarin compounds. Phthalocyanine-coumarin-crown ether complexes were sytnhesized using 7,8-(12-crown-4)-3-[p-(3,4-dicyanophenoxy)phenyl]coumarin, 7,8-(12-crown-4)-3-[p-(2,3-dicyanophenoxy)phenyl]coumarin, 7,8-(15-crown-5)-3-[p-(3,4-dicyano-phenoxy)phenyl]coumarin and 7,8-(15-crown-5)-3-[p-(2,3-dicyanophenoxy)-phenyl]coumarin compounds. Also novel water soluble phthalocyanines were obtained from 4-chloro-5-(4-phenyloxyacetic acid)phthalonitrile, 4,5-bis(phenyloxyacetic acid)phthalonitrile and 4-hexylthio-5-(4-phenyloxyacetic acid)phthalonitrile compounds. Zinc metallo phthalocyanine bearing eight coumarins at peripheral positions was synthesized from 4,5-bis[7-hexyloxy-3-(4-oxyphenyl)coumarin]phthalonitrile. The structure of new compounds were determined based on the results of spectroscopic methods such as FT-IR, UV/ Vis, 1H-NMR ve MALDI-TOF. Their fluorescence properties were investigated.