Synthesis, Characterization and Investigation of Some Features of New Functional Phthalocyanines

Abstract

Bu çalışmada; (i) 2,2'-(4-metilfenilimino)dietanol ve 4-nitroftalonitrilden türetilen 4-(2-((2-hidroksietil)(p-tolil)amino)etoksi)ftalonitril (3) ve 4,4'-(((p-tolilazandiil)bis(etan-2,1-diil)bis(oksi)diftalonitril (8), (ii) 2,2'-(4-metilfenilimino)dietanol ve 4,5-dikloroftalonitrilden türetilen 4-kloro-5-(2-((2-hidroksietil)(p-tolil)amino)etoksi)ftalonitril (14), (iii) 5-(4-hidroksifenil)-5-fenilhidantoin ile 4- nitroftalonitrilden türetilen 4-(4-(2,5-diokso-4-fenilimidazolidin-4-il)fenoksi)ftalonitril (19) bileşikleri sentezlendi. Bu ftalonitril türevlerinin farklı metal tuzları ile uygun reaksiyon şartlarında siklotetramerizasyonundan onbeş farklı metalliftalosiyanin elde edildi. Sentezlenen metalliftalosiyaninlerin agregasyon özellikleri derişime bağlı olarak incelendi. Elde edilen tüm bileşiklerin yapıları; elementel analiz (EA), infrared (FT-IR), nükleer manyetik rezonans (1H-NMR), ultraviyole-görünür ışık (UV-Vis) ve kütle (LCMS/MS, MALDI-TOF) spektral verileri kullanılarak aydınlatıldı. Bunlara ek olarak sentezlenen tüm bileşiklerin antioksidan özellikleri; DPPH giderme, metal şelatlama ve indirgeyici güç aktivite tayin metotları kullanılarak belirlendi. Son olarak tüm bileşiklerin gram-pozitif ve gram-negatif bakterilere karşı antimikrobiyal özellikleri de incelendiIn this study, (i) (2-((2-hydroxyethyl)(p-tolyl)amino)ethoxy)phthalonitrile (3) and 4,4'-(((p-tolylazanedyil)bis(ethane-2,1-diyl)bis(oxy)diphthalonitrile (8) were synthesized throughout the reaction of 2,2'-(4-methylphenylimino)diethanol with 4-nitrophthalonitrile in different molar concentrations. (ii) 4-chloro-5-(2-((2-hydroxyethyl)(p-tolyl)amino)ethoxy)phthalonitrile (14) and 4-(4-(2,5-dioxo-4-phenylimidazolidin-4-yl)phenoxy)phthalonitrile (19) were synthesized by the series reactions of 2,2'-(4-methylphenylimino)diethanol with 4,5-dichlorophthalonitrile, and (iii) 5-(4-hydroxyphenyl)-5-phenylhydantoin with 4-nitrophthalonitrile. Fifteen different metallophthalocyanines were synthesized from cyclotetramerisation of these phthalonitrile derivatives with different metal salts under mild reaction conditions. The aggregation behaviours of as synthesized metallophthalocyanines were investigated depending on concentration. The structures of these compounds were characterized by using elemental analysis (EA), Fourier Transform Infrared (FT-IR), Nuclear magnetic resonance (1H-NMR), Ultraviolet–visible (UV-Vis) and mass (LCMS/MS, MALDI-TOF) spectral data. Additionally, the antioxidant properties of these compounds were analyzed the methods of DPPH scaveging activity, metal chelating activity, and reducing power activity methods. Finally, antimicrobial properties of the some compounds against gram-positive and gram-negative bacteria were also investigated.