The Characterization and Synthesis of 4-(2-Phenoxy-1, 3-Dioxo-2, 3-Dihydro-1h-Inden-2-Yloxy) Phthalonitrile Substituted Phthalocyanines
Abstract
Bu çalışmada, yeni bir ftalonitril türevi 3 ninhidrin ile 4-nitroftalonitril'in bir nükleofilik yer değiştirime reaksiyonu ile hazırlandı. Yeni 4-(2-fenoksi-1, 3-diokso-2, 3-dihidro-1H-inden-2-iloksi)ftalonitril gruplu dört periferalı mono-nükleer metalloftalosiyaninler [M: Zn(II),Co(II),Cu(II),Ni(II),Mg(II)] 4-8 ftalonitril türevinin 3' ün siklotetramerizasyonu ile sentezlendi. Ftalosiyanin 4`ün fonksiyonel grubu karboksilik asit substituentli ftalosiyanine dönüştürmek için NaOH ile reaksiyona sokuldu. Böylece, Periferal pozisyonunda siyano grupları taşıyan ftalosiyanin 4 kompleksi NaOH/HCl ortamında hidrolizi ile karboksilik asit gruplarına dönüştü. Bu bileşik sodyum tuzları olarak suda çözünür.Sonra, Bileşik 4-8'in termal özellikleri azot atmosferinde 30-900 ?C sıcaklık aralığında TG (Termogravimetri) ve DTA (Diferansiyel Termik Analiz) ile incelendi. Sentezlenen bileşiklerin yapıları elemental analiz, FTIR, 1H-NMR ve UV-VIS spektral veri ile karakterize edildi.
In this work, A new substituted phthalonitrile derivative 3 was prepared by a nucleophilic displacement reaction of ninhydrin with 4-nitrophthalonitrile. Novel mono-nuclear metallophthalocyanines [M: Zn(II),Co(II),Cu(II),Ni(II),Mg(II)] 4-8 with four peripheral 4-(2-phenoxy-1, 3-dioxo-2, 3-dihydro-1H-inden-2-yloxy) phthalonitrile groups were synthesized by cyclotetramerization of phthalonitrile derivative 3. Functional group of phthalocyanine 4 was reacted with NaOH to obtain carboxylic acid substituted phthalocyanine. So, phthalocyanine complex 4 having terminal cyano groups in the peripheral were changed into carboxylic acid groups by hydrolysis in medium NaOH/HCl. This compound is soluble in water as sodium salts.Then, thermal properties of compounds 4-8 were investigated by TG (thermal gravimeter) and DTA (differential thermal analysis) in the temperature range of 30-900 ?C in nitrogen atmosphere. The structures of the synthesized compounds were characterized by elemental analysis, FTIR, 1H-NMR and UV-VIS spectral data.
In this work, A new substituted phthalonitrile derivative 3 was prepared by a nucleophilic displacement reaction of ninhydrin with 4-nitrophthalonitrile. Novel mono-nuclear metallophthalocyanines [M: Zn(II),Co(II),Cu(II),Ni(II),Mg(II)] 4-8 with four peripheral 4-(2-phenoxy-1, 3-dioxo-2, 3-dihydro-1H-inden-2-yloxy) phthalonitrile groups were synthesized by cyclotetramerization of phthalonitrile derivative 3. Functional group of phthalocyanine 4 was reacted with NaOH to obtain carboxylic acid substituted phthalocyanine. So, phthalocyanine complex 4 having terminal cyano groups in the peripheral were changed into carboxylic acid groups by hydrolysis in medium NaOH/HCl. This compound is soluble in water as sodium salts.Then, thermal properties of compounds 4-8 were investigated by TG (thermal gravimeter) and DTA (differential thermal analysis) in the temperature range of 30-900 ?C in nitrogen atmosphere. The structures of the synthesized compounds were characterized by elemental analysis, FTIR, 1H-NMR and UV-VIS spectral data.
Description
Keywords
Kimya, Ftalosiyaninler, Mononükleer Kompleksler, Sentez, Termal, Chemistry, Phthalocyanines, Mononuclear Complexes, Synthesis, Thermal
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