Publication: 3,4,5-Trimetoksifenoksi grupları içeren alfa ve beta sübstitüe metalli ve metalsiz ftalosiyanin bileşiklerinin sentezi ve karakterizasyonu
Abstract
3,4,5-TRİMETOKSİFENOKSİ GRUPLARI İÇEREN ALFA VE BETA SÜBSTİTÜE METALLİ VE METALSİZ FTALOSİYANİN BİLEŞİKLERİNİN SENTEZİ VE KARAKTERİZASYONU Ftalosiyaninler (Pc’ler) azot atomları ile birbirine bağlı dört izoindolin ünitesinden oluşan 18 π-elektron sistemine sahip aromatik bileşiklerdir. Bu makro halkalı bileşikler iki boyutlu π-elektron delokalizasyona sahiptir. Bu özelliklerinden dolayı ftalosiyaninler sıradışı optiksel ve elektriksel davranışlar gösteren, kimyasal ve termal olarak dayanıklı bileşiklerdir. Bu yüzden malzeme biliminde çok geniş bir uygulama alanları vardır [1,2]. Uzun yıllardır Pc bileşikleri organik pigmentler ve boyar madde olarak yaygın kullanılmaktadır. Geleneksel alandaki bu uygulamalardan başka, ftalosiyanin bileşikleri son yıllarda; sağlık (fotodinamik kanser tedavisi), elektrokromik görüntüleme cihazları, non-linear optik, optik bilgi depolama aygıtları, kimyasal sensörler, Langmuir- Blodgett filmler, fotoiletkenler ve sıvı kristaller gibi alanlarda kullanılmaktadır [4-14]. Bu çalışmada, 3,4,5-trimetoksifenolün 3-nitroftalonitril, 4-nitroftalonitril, ve 4,5-dikloroftalonitril bileşikleriyle nükleofilik yerdeğiştirme reaksiyonundan sırasıyla 3-(3,4,5-trimetoksifenoksi)ftalonitril, 4-(3,4,5-trimetoksifenoksi)ftalonitril, ve 5-kloro-4-(3,4,5-trimetilfenoksi)ftalonitril bileşikleri sentezlendi. Daha sonra bu başlangıç bileşikleri kullanılarak onların oksijen köprülü metalsiz ve Co, Fe, Zn metalli ftalosiyaninleri sentezlendi. Bileşiklerin karakterizasyonları 1H-NMR, UV-vis, IR and MALDI-TOF-MS spektroskopileriyle yapıldı. Orijinal Pc bileşiklerinin elektronik absorpsiyonları diklorometan, kloroform, toluen ve dimetilsülfoksit çözücülerinde çalışıldı. Ayrıca yeni ftalosiyanin bileşiklerinin elektrokimyasal özellikleri de Çanakkale Onsekiz Mart Üniversitesi Kimya Bölümündeki Doç Dr. Sermet KOYUNCU, Yrd. Doç Dr. Mehmet PİŞKİN ve arkadaşları tarafından araştırılmaktadır. Elektrokimya çalışmasına ait veriler teze dahil edimemiştir. Sonuçları teze ait verilerle birlikte uluslararası makale olarak değerlendirilecektir. Ftalosiyanin, trimetoksifenoksi, alfa, beta, metalli ftalosiyanin
SYNTHESIS AND CHARACTERIZATION OF ALPHA AND BETA SUBSTITUTED METALLO AND METAL-FREE PHTHALOCYANINES BEARING 3,4,5 TRIMETHOXYPHEOXY GROUPS Phthalocyanines (Pc) are 18 aromatic compounds having π-electron system and composed from four isoindoline unit connected with the nitrogen atoms each other. This macro cyclic compounds possess π-electron delocalization with two-dimensional. Pcs are chemically and thermally resistant compounds and exhibit unusual optical and electrical behaviours due to their property. Thus they have a very wide range of applications in the materials science field [1,2]. Pc compounds are used as organic pigments and dyes for many years. Apart from applications in traditional fields, Pcs are used in areas as photodynamic cancer therapy, electrochromic display devices, non-linear optics, optical data storage devices, Langmuir- Blodgett films, and liquid crystals, chemical sensors. [4-14]. In the present study, 3-(3,4,5-trimethoxyphenoxy)phthalonitrile, 4-(3,4,5-trimethoxyphenoxy)phthalonitrile and 5-chloro-4-(3,4,5trimethoxyphenoxy)phthalonitrile were synthesized with nucleophilic substitution reaction of 3,4,5-trimethoxyphenol and 3-nitrophthalonitrile, 4-nitrophthalonitrile, 3,4-dichlorophthalonitrile, respectively. Subsequently, their oxo bridged metal-free and metallo-Pcs (Co, Fe, and Zn) have been synthesized successfully. The characterization of the compounds was achieved by 1H-NMR, UV-vis, IR and MALDI-TOF-mass spectroscopies. The electronic absorption properties of newly synthesized compounds were also investigated in dichloromethane, chloroform, toluene and dimethylsulfoxide. The electrochemical properties of the novel are examined by the Doç Dr. Sermet KOYUNCU, Yrd and Doç Dr. Mehmet PİŞKİN at the chemistry department in Çanakkale Onsekiz Mart University. The electrochemical study was not included in this thesis, their data will be used in international article. Phthalocyanine, trimethoxyphenoxy , metallo phthalocyanine, alpha, beta.
SYNTHESIS AND CHARACTERIZATION OF ALPHA AND BETA SUBSTITUTED METALLO AND METAL-FREE PHTHALOCYANINES BEARING 3,4,5 TRIMETHOXYPHEOXY GROUPS Phthalocyanines (Pc) are 18 aromatic compounds having π-electron system and composed from four isoindoline unit connected with the nitrogen atoms each other. This macro cyclic compounds possess π-electron delocalization with two-dimensional. Pcs are chemically and thermally resistant compounds and exhibit unusual optical and electrical behaviours due to their property. Thus they have a very wide range of applications in the materials science field [1,2]. Pc compounds are used as organic pigments and dyes for many years. Apart from applications in traditional fields, Pcs are used in areas as photodynamic cancer therapy, electrochromic display devices, non-linear optics, optical data storage devices, Langmuir- Blodgett films, and liquid crystals, chemical sensors. [4-14]. In the present study, 3-(3,4,5-trimethoxyphenoxy)phthalonitrile, 4-(3,4,5-trimethoxyphenoxy)phthalonitrile and 5-chloro-4-(3,4,5trimethoxyphenoxy)phthalonitrile were synthesized with nucleophilic substitution reaction of 3,4,5-trimethoxyphenol and 3-nitrophthalonitrile, 4-nitrophthalonitrile, 3,4-dichlorophthalonitrile, respectively. Subsequently, their oxo bridged metal-free and metallo-Pcs (Co, Fe, and Zn) have been synthesized successfully. The characterization of the compounds was achieved by 1H-NMR, UV-vis, IR and MALDI-TOF-mass spectroscopies. The electronic absorption properties of newly synthesized compounds were also investigated in dichloromethane, chloroform, toluene and dimethylsulfoxide. The electrochemical properties of the novel are examined by the Doç Dr. Sermet KOYUNCU, Yrd and Doç Dr. Mehmet PİŞKİN at the chemistry department in Çanakkale Onsekiz Mart University. The electrochemical study was not included in this thesis, their data will be used in international article. Phthalocyanine, trimethoxyphenoxy , metallo phthalocyanine, alpha, beta.