Fenantrolin sübstitüe sepet tipi ftalosiyaninlerin sentezi ve özelliklerinin incelenmesi
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Dosyalar
Tarih
2020
Yazarlar
Dergi Başlığı
Dergi ISSN
Cilt Başlığı
Yayıncı
İnönü Üniversitesi
Erişim Hakkı
info:eu-repo/semantics/openAccess
Özet
Ftalosiyaninler on yıllar boyunca hem farklı türevlerinin sentezi ve hem de farklı alanlarda uygulaması giderek artan makro moleküllerden biridir. Ftalosiyaninlerin periferal ve non-periferal konumlarında alkil, aril gibi çok farklı gruplar kullanılarak, metalsiz ve periyodik tablodaki çok sayıdaki metalle mononükleer, polinükler, sepet türü sayısız türevleri sentezlenmiştir. Sepet tipi ftalosiyanin ilk defa 2002 yılında Tomilova ve arkadaşları tarafından sentezlenmiştir. O günden bugüne aren, naftalin, kumarin, pentaeritritol gibi farklı köprü gruplar içeren sepet tipi ftalosiyanin türevlerinin sayısı giderek artmış ve elektriksel, elektrokimyasal, spektroelektrokimyasal, elektro katalitik, gaz sensör, fotofiziksel gibi özellikleri çalışılmıştır. Bu çalışmada, 4,7-dikloro-1,10-fenantrolin ve 4-hidroksiftalonitrilin K2CO3 varlığında tepkimesi ile 1,10-fenantrolin-4,7-disübstitüe ftalonitril 1 hazırlandı. 1 bileşiğinin hidrokinonda tetramerizasyonu sonucu veya lityum metali ya da MgCl2.6H2O ile tetramerizasyonu ile oluşan ürünün asidik hidrolizi sonucu 4,7-fenantrolin sübstitüe sepet tipi metalsiz ftalosiyanin 2 bileşiği elde edildi. 1 bileşiğinin Fe(AcO)2 ya da Mn(AcO)2.4H2O ile tetramerizasyonu sonucu metalli sepet tipi ftalosiyaninler 3 ve 4 elde edildi.5,6-Bis(2-hidroksietoksi)-1,10-fenantrolin ile 4-nitroftalonitrilin K2CO3 varlığında tepkimesi ile 1,10-fenantrolin-5,6-disübstitüe ftalonitril türevi 6 sentezlendi. 6 bileşiğinin hidrokinonda tetramerizasyonu sonucu veya lityum metali ya da MgCl2.6H2O ile tetramerizasyonu sonucu oluşan ürünün asidik hidrolizi sonucu 5,6-fenantrolin sübstitüe sepet tipi metalsiz ftalosiyanin 7 bileşiği elde edildi. 6 bileşiğinin Fe(AcO)2 ya da Mn(AcO)2.4H2O ile tetramerizasyonu sonucu metalli sepet tipi ftalosiyaninler 8 ve 9 elde edildi. Hazırlanan bileşikler 1H-NMR, 13C-NMR, UV-VIS, IR, Kütle spektrometreleri ve elementel analiz ile karakterize edildi. Fenantrolin sübstitüye ftalosiyaninlerin agregasyon davranışları çözücüye ve derişime bağlı olarak incelendi.
Phthalociyanines are one of the macromolecules, which have increasing number of derivatives being synthesized and have greatly growing number of applications in various fields for decades. Phthalocyanines with different groups such as alkyl and aryl substituents on the periphery and non-periphery were synthesized in different types like mononuclear, polynuclear and ball-type and either with many metals in periodic table or metal-free. The Ball-type phthalocyanine was first synthesized by Tomilova et. al in 2002. Upto now, number of ball-type phthalocyanines containing different bridging groups such as aren, naphtalene, cumarine, pentaerithiole, rapidly increased and differrent properties, such as electrical, electrochemical, spectroelectrochemical, electrocatalytic, gas sensor, photophysical are studied. In the present work, 1,10-phenanthroline-4,7-disubstituted phthalonitrile 1 was prepared by the reaction of 4-hydroxophthalonitrile and 4,7-dichloro-1,10-phenanthroline in the presence of K2CO3. 4,7- phenanthroline substituted ball-type metal-free phthalocyanine 2 was obtained by the tetramerization of compound 1 in hydroquinone or tetramerization of compound with metalic lithium or MgCl2.6H2O and then its acidic hydrolysis. Metalloball-type phthalocyanines 3 and 4 were obtained by the reaction of compound 1 with Fe(AcO)2 or Mn(AcO)2.4H2O. 1,10-phenanthroline-5,6-disubstituted phthalonitrile derivative 6 was prepared by the reaction of 4-nitrophthalonitrile and 5,6-bis(2-hydroxoetoxy)-1,10-phenanthroline in the presence of K2CO3. 5,6-phenanthroline substituted ball-type metal-free phthalocyanine 7 was obtained by the tetramerization of compound 6 in hydroquinone or tetramerization of compound 1 with metalic lithium or MgCl2.6H2O and then its acidic hydrolysis. Metalloball-type phthalocyanines 8 and 9 were obtained by the reaction of compound 7 with Fe(AcO)2 or Mn(AcO)2.4H2O. Prepared compounds were characterized by 1H-NMR, 13C-NMR, UV-VIS, IR, mass spectrometers and elemental analysis. The aggregation behaviors of phenanthroline substituted phthalocyanines were studied depend on solvents and concentrations.
Phthalociyanines are one of the macromolecules, which have increasing number of derivatives being synthesized and have greatly growing number of applications in various fields for decades. Phthalocyanines with different groups such as alkyl and aryl substituents on the periphery and non-periphery were synthesized in different types like mononuclear, polynuclear and ball-type and either with many metals in periodic table or metal-free. The Ball-type phthalocyanine was first synthesized by Tomilova et. al in 2002. Upto now, number of ball-type phthalocyanines containing different bridging groups such as aren, naphtalene, cumarine, pentaerithiole, rapidly increased and differrent properties, such as electrical, electrochemical, spectroelectrochemical, electrocatalytic, gas sensor, photophysical are studied. In the present work, 1,10-phenanthroline-4,7-disubstituted phthalonitrile 1 was prepared by the reaction of 4-hydroxophthalonitrile and 4,7-dichloro-1,10-phenanthroline in the presence of K2CO3. 4,7- phenanthroline substituted ball-type metal-free phthalocyanine 2 was obtained by the tetramerization of compound 1 in hydroquinone or tetramerization of compound with metalic lithium or MgCl2.6H2O and then its acidic hydrolysis. Metalloball-type phthalocyanines 3 and 4 were obtained by the reaction of compound 1 with Fe(AcO)2 or Mn(AcO)2.4H2O. 1,10-phenanthroline-5,6-disubstituted phthalonitrile derivative 6 was prepared by the reaction of 4-nitrophthalonitrile and 5,6-bis(2-hydroxoetoxy)-1,10-phenanthroline in the presence of K2CO3. 5,6-phenanthroline substituted ball-type metal-free phthalocyanine 7 was obtained by the tetramerization of compound 6 in hydroquinone or tetramerization of compound 1 with metalic lithium or MgCl2.6H2O and then its acidic hydrolysis. Metalloball-type phthalocyanines 8 and 9 were obtained by the reaction of compound 7 with Fe(AcO)2 or Mn(AcO)2.4H2O. Prepared compounds were characterized by 1H-NMR, 13C-NMR, UV-VIS, IR, mass spectrometers and elemental analysis. The aggregation behaviors of phenanthroline substituted phthalocyanines were studied depend on solvents and concentrations.
Açıklama
Anahtar Kelimeler
Kimya, Chemistry
Kaynak
WoS Q Değeri
Scopus Q Değeri
Cilt
Sayı
Künye
Gürel, İ. (2020). Fenantrolin sübstitüe sepet tipi ftalosiyaninlerin sentezi ve özelliklerinin incelenmesi. Yayınlanmış Doktora Tezi, İnönü Üniversitesi.
