Sübstitüe hekzaaminobenzen ve komplekslerinin sentezi
Synthesis and characterization of 2,3,6,7,10,11, hexakis (2-hidroxyphenly) dipyrazino (2,3-f:2,3-h) quinoxaline and its nickel (II) complex
- Tez No: 21823
- Danışmanlar: PROF. DR. ÖZER BEKAROĞLU
- Tez Türü: Yüksek Lisans
- Konular: Kimya, Chemistry
- Anahtar Kelimeler: Hekzaaminobenzen, Koordinasyon bileşikleri, Hexaaminobenzene, Coordination compounds
- Yıl: 1992
- Dil: Türkçe
- Üniversite: İstanbul Teknik Üniversitesi
- Enstitü: Fen Bilimleri Enstitüsü
- Ana Bilim Dalı: Belirtilmemiş.
- Bilim Dalı: Belirtilmemiş.
- Sayfa Sayısı: Belirtilmemiş.
Özet
found, whereas at higher concentrations a second mesophase exists with hexagonal structure. 1, 3, 5-Triamino-2, 4, 6-trinitrobenzene is hydrogena ted to obtain hexaaminobenzene which is reacted with nona- noyl chloride to prepare 1, 2, 3, 4, 5, 6-hexakis (nonanoy- lamino) benzene. - This x& used as component of lytropic liquid-crystal phases, which can be used in display devices, Discotic liquid crystals are receiving extensive research interest since there first appearance in the lite rature about 15 years ago. Planar molecules with aromatic character, such as-phthalocyanines or hexaaminobenzene deri vatives, are the first candidates for preparing new disco- tis mesogens. The aim of this study is to synthesize new derivatives of hexaaminobenzene carrying additional donor sites to bind transition metal ions in order to enhance the planarity of the molecule. For this purpose, the con densation product of 2,2 ' -dihydroxybenzil and hexaamino benzene are chosen as starting materials. The first step is the synthesis of 2} 2 ' -dihydroxyben zil. 2-Methoxybenzaldehyde was first prepared by the careful methylation of salicylaldehyde with dimethylsulp- hate. The boiling point of the product is 236-237°C. 2, 2 ' -Dimethoxybenzoin ? was prepared by the action of potassium cyanide on 2-methoxybenzaldehyde in ethanol. The oil which seperated was extracted- with diethylether. The solvent was removed and the residual oil was used directly in the oxidation. The oxidation of benzoin to 2,2 ' -dimethoxybenzil was prepared by Fettling solution. The colourless product melts at 130°C. 2,2 ' -Dimethoxybenzil was dissolved in nitrobenzene and AlClo was added. The mixture was heated under reflux for 7 hours. The residue was recrystallized from 70% CH3 COOH. The product is yellow and melts of 154-155°C 1, 3, 5-Trichloro-2, 4, 6-trinitrobenzene was prepa red by the nitration of 1, 3,5-trichlorobenzene. Then in toluen 1, 3,5-triaamino-2, 4, 6-trinitrobenzene was prepared by bub ling gaseous dry ammonia. IX
Özet (Çeviri)
Hexaaminobenzene was prepared by reduction of 1, 3, 5- triamino-2, 4, 6 trinitrobenzene with phenylhydrazine. A new ligand, 2, 3, 6, 7, 10, 11-hexakis (2-hydroxyphenyl) dipyrazino [2,3-f:2', 3 ' -h] quinoxaline was prepared by reaction of hexaaminobenzene and 2, 2“ -dihydroxybenzil. In order to prepare tris (nickel II) complex, 2, 3, 6, 7, 10, 11-hexakis (2-hydroxyphenyl) dipyrazino allowed to react with Nickel (II) acetate tetrahydrate in 1:3 ratio in DMF for 2 hours.found, whereas at higher concentrations a second mesophase exists with hexagonal structure. 1, 3, 5-Triamino-2, 4, 6-trinitrobenzene is hydrogena ted to obtain hexaaminobenzene which is reacted with nona- noyl chloride to prepare 1, 2, 3, 4, 5, 6-hexakis (nonanoy- lamino) benzene. - This x& used as component of lytropic liquid-crystal phases, which can be used in display devices, Discotic liquid crystals are receiving extensive research interest since there first appearance in the lite rature about 15 years ago. Planar molecules with aromatic character, such as-phthalocyanines or hexaaminobenzene deri vatives, are the first candidates for preparing new disco- tis mesogens. The aim of this study is to synthesize new derivatives of hexaaminobenzene carrying additional donor sites to bind transition metal ions in order to enhance the planarity of the molecule. For this purpose, the con densation product of 2,2 ' -dihydroxybenzil and hexaamino benzene are chosen as starting materials. The first step is the synthesis of 2} 2 ' -dihydroxyben zil. 2-Methoxybenzaldehyde was first prepared by the careful methylation of salicylaldehyde with dimethylsulp- hate. The boiling point of the product is 236-237°C. 2, 2 ' -Dimethoxybenzoin ? was prepared by the action of potassium cyanide on 2-methoxybenzaldehyde in ethanol. The oil which seperated was extracted- with diethylether. The solvent was removed and the residual oil was used directly in the oxidation. The oxidation of benzoin to 2,2 ' -dimethoxybenzil was prepared by Fettling solution. The colourless product melts at 130°C. 2,2 ' -Dimethoxybenzil was dissolved in nitrobenzene and AlClo was added. The mixture was heated under reflux for 7 hours. The residue was recrystallized from 70% CH3 COOH. The product is yellow and melts of 154-155°C 1, 3, 5-Trichloro-2, 4, 6-trinitrobenzene was prepa red by the nitration of 1, 3,5-trichlorobenzene. Then in toluen 1, 3,5-triaamino-2, 4, 6-trinitrobenzene was prepared by bub ling gaseous dry ammonia. IXHexaaminobenzene was prepared by reduction of 1, 3, 5- triamino-2, 4, 6 trinitrobenzene with phenylhydrazine. A new ligand, 2, 3, 6, 7, 10, 11-hexakis (2-hydroxyphenyl) dipyrazino [2,3-f:2', 3 ' -h] quinoxaline was prepared by reaction of hexaaminobenzene and 2, 2 ”-dihydroxybenzil. In order to prepare tris (nickel II) complex, 2, 3, 6, 7, 10, 11-hexakis (2-hydroxyphenyl) dipyrazino allowed to react with Nickel (II) acetate tetrahydrate in 1:3 ratio in DMF for 2 hours.found, whereas at higher concentrations a second mesophase exists with hexagonal structure. 1, 3, 5-Triamino-2, 4, 6-trinitrobenzene is hydrogena ted to obtain hexaaminobenzene which is reacted with nona- noyl chloride to prepare 1, 2, 3, 4, 5, 6-hexakis (nonanoy- lamino) benzene. - This x& used as component of lytropic liquid-crystal phases, which can be used in display devices, Discotic liquid crystals are receiving extensive research interest since there first appearance in the lite rature about 15 years ago. Planar molecules with aromatic character, such as-phthalocyanines or hexaaminobenzene deri vatives, are the first candidates for preparing new disco- tis mesogens. The aim of this study is to synthesize new derivatives of hexaaminobenzene carrying additional donor sites to bind transition metal ions in order to enhance the planarity of the molecule. For this purpose, the con densation product of 2,2 ' -dihydroxybenzil and hexaamino benzene are chosen as starting materials. The first step is the synthesis of 2} 2 ' -dihydroxyben zil. 2-Methoxybenzaldehyde was first prepared by the careful methylation of salicylaldehyde with dimethylsulp- hate. The boiling point of the product is 236-237°C. 2, 2 ' -Dimethoxybenzoin ? was prepared by the action of potassium cyanide on 2-methoxybenzaldehyde in ethanol. The oil which seperated was extracted- with diethylether. The solvent was removed and the residual oil was used directly in the oxidation. The oxidation of benzoin to 2,2 ' -dimethoxybenzil was prepared by Fettling solution. The colourless product melts at 130°C. 2,2 ' -Dimethoxybenzil was dissolved in nitrobenzene and AlClo was added. The mixture was heated under reflux for 7 hours. The residue was recrystallized from 70% CH3 COOH. The product is yellow and melts of 154-155°C 1, 3, 5-Trichloro-2, 4, 6-trinitrobenzene was prepa red by the nitration of 1, 3,5-trichlorobenzene. Then in toluen 1, 3,5-triaamino-2, 4, 6-trinitrobenzene was prepared by bub ling gaseous dry ammonia. IXHexaaminobenzene was prepared by reduction of 1, 3, 5- triamino-2, 4, 6 trinitrobenzene with phenylhydrazine. A new ligand, 2, 3, 6, 7, 10, 11-hexakis (2-hydroxyphenyl) dipyrazino [2,3-f:2', 3 ' -h] quinoxaline was prepared by reaction of hexaaminobenzene and 2, 2 " -dihydroxybenzil. In order to prepare tris (nickel II) complex, 2, 3, 6, 7, 10, 11-hexakis (2-hydroxyphenyl) dipyrazino allowed to react with Nickel (II) acetate tetrahydrate in 1:3 ratio in DMF for 2 hours.
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