Piridin sübstitüye ftalosiyaninlerin sentezi ve özelliklerinin incelenmesi
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Dosyalar
Tarih
2011
Yazarlar
Dergi Başlığı
Dergi ISSN
Cilt Başlığı
Yayıncı
İnönü Üniversitesi
Erişim Hakkı
info:eu-repo/semantics/openAccess
Özet
Ftalosiyaninlerin elektriksel, optik, katalitik özelliklerinden dolayı gaz sensör, yarıiletken ve güneş pilleri gibi malzemelerin hazırlanması, katalitik tepkimeler ve fotodinamik kanser tedavisi gibi birçok farklı alanda kullanıldıkları görülmektedir. Piridin ve türevleri de farmakolojik, optik ve katalitik özelliklerinden dolayı birçok uygulama alanında kullanılmaktadır. Bu nedenle periferal konumda piridin türevleri içeren ftalosiyaninlerin hazırlanması ve karakterizasyonu ilginç olacaktır. Bu çalışmada, 4,5-dihidroksiftalonitril ve 2-kloro-5-nitropiridinin K2CO3 varlığında tepkimesi ile 5-nitropiridin disübstitüye ftalonitril 3 hazırlandı. 3 bileşiğinin hidrokinonda tetramerizasyonu sonucu 5-nitropiridin oktasübstitüye metalsiz ftalosiyanin 4 elde edildi. 3 bileşiğinin kinolinde Zn(OAc)2 ya da Co(OAc)2.4H2O ile tepkimesi sonunda 5-nitropiridin oktasübstitüye metalli ftalosiyaninler 5 ve 6 elde edildi. 5-nitropiridin disübstitüye ftalonitril 3 bileşiğinin %10 Pd/C katalizör varlığında indirgenmesi sonucu 5-aminopiridin disübstitüye ftalonitril 7 hazırlandı. 7 bileşiğinin lityum metali varlığında tetramerizasyonu ve asidik hidrolizi ile 5-aminopiridin oktasübstitüye metalsiz ftalosiyanin 8 elde edildi. 7 bileşiğinin1,8-Diazabisiklo[5.4.0]-undek-7-en (DBU) varlığında Zn(OAc)2 ya da Co(OAc)2.4H2O ile tepkimesi sonunda 5-aminopiridin oktasübstitüye metalli ftalosiyaninler 9 ve 10 elde edildi. Hazırlanan bileşikler 1H-NMR, 13C-NMR, UV-VIS, IR spektroskopisi ve Elementel Analiz ile karakterize edildi. Piridin sübstitüye ftalosiyaninlerin agregasyon davranışları çözücüye ve derişime bağlı olarak incelendi.
Due to their electrical, optical, catalytic properties, phthalocyanines have been used in many different areas such as in gas sensors, preparation of materials such as semiconductor and solar cells, in catalytic reactions and photodynamic cancer therapy. Pyridine and its derivatives have been used in many applications due to their pharmacologycal, optical and catalytic properties. Therefore, the preparation and characterization of phthalocyanines containing pyridine derivatives on periferal position would be interesting. In the present work, 5-nitropyridine disubstituted phthalonitrile 3 was prepared by the reaction of 4-dihydroxyphthalonitrile and 2-chloro-5-nitropyridine in the presence of K2CO3. 5-nitropyridine octasubstituted metal-free phthalocyanine 4 was obtained by the tetramerization of compound 3 in hydroquinone. 5-nitropyridine octasubstituted metallo phthalocyanines 5 and 6 were obtained by the reaction of compound 3 with Zn(OAc)2 or Co(OAc)2.4H2O in quinoline. 5-aminopyridine disubstituted phthalonitrile 7 was prepared by the reduction of compound 3 in the presence of 10% Pd/C catalyst. 5-aminopyridine octasubstituted metal-free phthalocyanine 8 was obtained by the tetramerization of compound 7 with metalic lithium and then its acidic hydrolysis. 5-aminopyridine octasubstituted metallo phthalocyanines 9 and 10 were obtained by the reaction of compound 7 with Zn(OAc)2 or Co(OAc)2.4H2O in the presence of DBU. Prepared compounds were characterized by 1H-NMR, 13C-NMR, UV-VIS, IR spectroscopy and elemental analysis. The aggregation behaviors of pyridine substituted phthalocyanines were studied depend on solvents and concentrations.
Due to their electrical, optical, catalytic properties, phthalocyanines have been used in many different areas such as in gas sensors, preparation of materials such as semiconductor and solar cells, in catalytic reactions and photodynamic cancer therapy. Pyridine and its derivatives have been used in many applications due to their pharmacologycal, optical and catalytic properties. Therefore, the preparation and characterization of phthalocyanines containing pyridine derivatives on periferal position would be interesting. In the present work, 5-nitropyridine disubstituted phthalonitrile 3 was prepared by the reaction of 4-dihydroxyphthalonitrile and 2-chloro-5-nitropyridine in the presence of K2CO3. 5-nitropyridine octasubstituted metal-free phthalocyanine 4 was obtained by the tetramerization of compound 3 in hydroquinone. 5-nitropyridine octasubstituted metallo phthalocyanines 5 and 6 were obtained by the reaction of compound 3 with Zn(OAc)2 or Co(OAc)2.4H2O in quinoline. 5-aminopyridine disubstituted phthalonitrile 7 was prepared by the reduction of compound 3 in the presence of 10% Pd/C catalyst. 5-aminopyridine octasubstituted metal-free phthalocyanine 8 was obtained by the tetramerization of compound 7 with metalic lithium and then its acidic hydrolysis. 5-aminopyridine octasubstituted metallo phthalocyanines 9 and 10 were obtained by the reaction of compound 7 with Zn(OAc)2 or Co(OAc)2.4H2O in the presence of DBU. Prepared compounds were characterized by 1H-NMR, 13C-NMR, UV-VIS, IR spectroscopy and elemental analysis. The aggregation behaviors of pyridine substituted phthalocyanines were studied depend on solvents and concentrations.
Açıklama
Anahtar Kelimeler
Ftalosiyanin, Piridin, Çinko, Kobalt, Agregasyon, Phthalocyanine, Pyridine, Zinc, Cobalt, Aggregation
Kaynak
WoS Q Değeri
Scopus Q Değeri
Cilt
Sayı
Künye
Gürel,İ. (2011). Piridin sübstitüye ftalosiyaninlerin sentezi ve özelliklerinin incelenmesi. İnönü Üniversitesi Fen Bilimleri Enstitüsü. 1-88 ss.
