5,6-DİAMİNOPİRİMİDİN SÜBSTİTÜE TOP-TİPİ METALLİ FTALOSİYANİNLERİN SENTEZİ VE KARAKTERİZASYONU

Abstract

İlk basamakta [4,4'-(5,6-diaminopirimidin-2,4-diil)-bis-(tiyo)]diftalonitrilin 1'in sentezi; 5,6-diaminopirimidin-2,4-ditiyol ve 4 ftalonitril (1:2) oranında potasyum karbonat varlığında, DMF' de, 70 oC' de, argon atmosferi altında nükleofilik aromatik sübstitüsyon tepkimesiyle gerçekleştirildi. İkinci basamakta sentezlenen bu diftalonitril bileşiğinin, siklotetramerizasyonu sonucunda top tipi metallo ftalosiyaninler [2', 10', 16', 24'-tetrakis{4,4'-(5,6-diaminopirimidin- 2,4-diil)-bis(tiyo)}] diftalosiyanindikobalt(II) 2, [2', 10', 16', 24'-tetrakis{4,4'-(5,6- diaminopirimidin-2,4-diil)-bis(tiyo)] diftalosiyanindikobalt(II) 3, [2', 10', 16', 24'- tetrakis{4,4'-(5,6-diaminopirimidin-2,4-diil)-bis(tiyo)}] diftalosiyanindinikel(II) 4, [2', 10', 16', 24'-tetrakis{4,4'-(5,6-diaminopirimidin-2,4-diil)-bis(tiyo)}] diftalosiyanindibakır(II) 5, DMF' de elde edilirken, [2', 10', 16', 24'-tetrakis{4,4'-(5,6-diaminopirimidin-2,4-diil)- bis(tiyo)}] diftalosiyaninlutesyum(III) 6 ise hekzanol' da elde edildi. Sentezlenen top tipi ftalosiyaninler 2, 3, 4, 5 ve 6 DMF ve DMSO da çözünür. Son basamakta sentezlenen bileşikler FT-IR, 1H-NMR, UV-VİS ve MALDI-TOF-MS spektral verileriyle karakterize edildi. Anahtar kelimeler : Top tipi ftalosiyaninler

In the first step; the synthesis of [4,4'-(5,6-diamino pyrimidine-2,4-diyl)-bis(tiyo)] diphtalonitrile 1 was performed by the method of nucheophilic aromatic substution based on the reaction of 5,6-diaminopyrimidine-2,4-dithiol and 4-nitrophthalonitrile (1:2) in ratio in DMF in the presence of anhydrous K2CO3 as the base, at 70 oC temperature, under argon atmosphere. In the second step; As a result of cyclotetramerization of the synthesized diphthalonitrile compound 1 were obtained the ball-type metallophthalocyanines [2', 10', 16', 24'-tetrakis{4,4'-(5,6-diaminopyrimidin-2,4-diyl)bis(tiyo)}] diphtalocyaninedicobalt(II) 2, [2', 10', 16', 24'-tetrakis{4,4'-(5,6-diaminopyrimidin-2,4-diyl)bis(tiyo)}] diphtalocyaninedizinc(II) 3, [2', 10', 16', 24'-tetrakis{4,4'-(5,6-diaminopyrimidin-2,4-diyl)bis(tiyo)}] diphtalocyaninedicupper( II) 4, and [2', 10', 16', 24'-tetrakis{4,4'-(5,6-diaminopyrimidin-2,4-diyl)bis(tiyo)}] diphtalocyaninedinickel(II) 5 in DMF while was obtained the [2', 10', 16', 24'-tetrakis{4,4'- (5,6-diaminopyrimidin-2,4-diyl)bis(tiyo)}] diphtalocyaninelutetium(III) 6 in hexanol. The synthesized ball-type phthalocyanines 2, 3, 4, 5, and 6 are dissolved in DMF and DMSO. In the last step; the synthesized compounds have been characterized by FT-IR, 1H NMR, UV–vis and MALDI-TOF MS spectral data. Keywords: Ball-type phthalocyanines;