Fonksiyonel gruplar içeren yeni tip ftalosiyanin bileşiklerinin sentezi ve özelliklerinin incelenmesi

Abstract

Bu tez çalışmasında, yeni 3-[4-(4,4,5,5-tetrametil-1,3,2-dioksaborolan-2-il) fenoksi] ftalonitril (12), 2(3), 9(10), 16(17), 23(24)-tetrakis-{4-[4-(4, 4, 5, 5-tetrametil-1, 3, 2-dioksaborolan-2-il)fenoksi]} ftalosiyaninato çinko (II) (13), 4-(4-(4,4,5,5-tetrametil-1,3,2-dioksaborolan-2-il) fenoksi) ftalonitril (14), 1(4), 8(11), 15(18), 22(25)-tetrakis(4-(4,4,5,5-tetrametil-1,3,2-dioksaborolan-2-il) fenoksi)] ftalosiyaninato çinko (II) (15), 4-kloro-5-(4-(4,4,5,5-tetrametil-1,3,2-dioksaborolan-2-il) fenoksi) ftalonitril (16), 2, 9, 16, 23-Tetrakloro-3,10,17,24-tetrakis(4-(4,4,5,5-tetrametil-1,3,2-dioksaborolan-2-il) fenoksi) ftalosiyaninato çinko (II) (17), 3-(4-iyodofenoksi)ftalonitril (18), 2(3), 9(10), 16(17), 23(24)-tetrakis(4-iyodofenoksi) ftalosiyaninato çinko (II) (19), 2(3), 9(10), 16(17), 23(24)-tetrakis(4-((trimetilsilil)etil)fenoksi) ftalosiyaninato çinko (II) (20) 4-(4-iyodofenoksi)ftalonitril (21), 1(4), 8(11), 15(18), 22(25)-tetrakis(4-iyodofenoksi) ftalosiyaninato çinko (II) (22), 1(4), 8(11), 15(18), 22(25)-tetrakis(4-((trimetilsilil)etinil)fenoksi) ftalosiyaninato çinko(II) (23), 4,5-bis(iyodofenoksi)ftalonitril (24), 2,3,9,10,16,17,23,24-oktakis(4-iyodofenoksi) ftalosiyaninato çinko (II) (25), 2,3,9,10,16,17,23,24-oktakis(4-((trimetilsilil)etil)fenoksi)ftalosiyaninato çinko (II) (26) bileşikleri sentezlenmiştir. Sentezlenen bileşiklerin yapıları FT-IR, MALDI-TOF, UV-Vis, 1H-NMR, 13C-NMR, 11B-NMR ve X-ray analiz sonuçları ile aydınlatılmıştır. Elde edilen ftalosiyanin bileşikleri fonksiyonel çekirdek moleküller (bulding block) olup bu bileşikler üzerinden Suzuki kenetlenme, Sonogashira kenetlenme ve "Click" reaksiyonu yöntemleri kullanılarak birçok uygulama alanında (sıvı kristal, katalizör, non-linear optik, PDT gibi) kullanılabilecek yeni ftalosiyanin bileşiklerinin sentezlenmesi mümkün olacaktır. Elde edilen yeni ftalosiyanin bileşiklerinin fotofiziksel ve fotokimyasal özellikleri incelenmiştir.In this thesis, new 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenoxy] phthalonitrile (12), 2(3), 9(10), 16(17), 23(24)-tetrakis-[(4-(4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) phenoxy)] phthalocyaninato zinc (II) (13), 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenoxy] phthalonitrile (14), 1(4),8(11),15(18),22(25)-tetrakis[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenoxy] phthalocyaninato zinc (II) (15), 4-chloro-5-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenoxy] phthalonitrile (16), 2,9,16,23-tetrachloro-3,10,17,24-tetrakis[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenoxy] phthalocyaninato zinc (II) (17), 3-(4-iodophenoxy) phthalonitrile (18), 2(3), 9(10), 16(17), 23(24)-tetrakis(4-iodophenoxy) phthalocyaninato zinc (II) (19), 2(3), 9(10), 16(17), 23(24)-tetrakis{4-[(trimethylsilyl) ethyl] phenoxy} phthalocyaninato zinc (II) (20) 4-(4-iodophenoxy) phthalonitrile (21), 1(4), 8(11), 15(18), 22(25)-tetrakis (4-iodophenoxy) phthalocyaninato zinc (II) (22), 1(4), 8(11), 15(18), 22(25)-tetrakis{4-[(trimethylsilyl) ethyl ) phenoxy]} phthalocyaninato zinc (II) (23), 4,5-bis (iodophenoxy) phthalonitrile (24), 2,3,9,10,16,17,23,24-octakis (4-iodophenoxy) phthalocyaninato zinc (II) (25), 2,3,9,10,16,17,23,24-octakis (4((trimethylsilyl) ethyl) phenoxy) phthalocyaninato zinc (II) (26) compounds were synthesized. The synthesized novel compounds have been characterized by FT-IR, MALDI-TOF, UV-Vis, 1H-NMR, 13C-NMR, 11B-NMR and X-ray analysis.The synthesized phthalocyanines can be used as building block molecules. It is possible to synthesize new phthalocyanine compounds which can be used in many application fields (liquid crystal, catalyst, non-linear optical, PDT, etc.) by using Suzuki coupling, Sonogashira coupling and "Click" reaction methods over these compounds. Their photophysical and photochemical properties will be examined.