Yeni heterosiklik disazo boyarmaddelerin sentezi ve spektroskopik özelliklerinin incelenmesi

Abstract

Bu çalışmada, ilk etapta anilin ve anilin türevleri 3-aminokrotononitril ile kenetlenmiş daha sonra hidrazin monohidrat ve fenil hidrazin ile halka kapama reaksiyonu sonucu 5-amino-4-arilazo-3-metil-1H-pirazol (2a-2e) ve 5-amino-4-arilazo-3-metil-1-fenil-pirazol (3a-3e) türevi mono azo boyarmaddeler sentezlenmiştir. İkinci aşamada sentezlenen bu bileşikler önce diazolanmış sonrasında etil benzoil asetat ile kenetlenmiş ve yine hidrazin mono hidrat ve fenil hidrazin ile halka kapama reaksiyonu sonucu bir seri 4-(4'-arilazo-3'-metil-1'-H-pirazol-5-ilazo)?3?fenil-1H?pirazol-5-on (4a-4e), 4-(4'-arilazo-3'-metil-1'-H-pirazol-5-ilazo)?1,3-difenil?pirazol-5-on (5a-5e), 4-(4'-arilazo-3'-metil-1'-fenil-pirazol-5-ilazo)?3?fenil-1H?pirazol-5-on (6a-6e) ve 4-(4'-arilazo-3'-metil-1'-fenil-pirazol-5-ilazo)?1,3?difenil pirazol-5-on (7a-7e) türevleri sentezlenmiştir. Sentezlenen disazo boyarmaddeler element analizi, UV, FT-IR ve 1H-NMR gibi spektral yöntemlerle karakterize edilmiş ve çözücü değişimi, elektron alıcı ve elektron verici grupların bağlı olmasının bu bileşiklerin absorpsiyon yeteneklerini nasıl etkilediği incelenmiştir.

In the first step of this study, aniline and aniline derivatives were diazotised and coupled with 3-aminocrotononitrile, later these compounds were reacted with hydrazine mono hydrate and phenyl hydrazine to give corresponding 5-amino-4-arylazo-3-methyl-1H-pyrazoles (2a-2e) and 5-amino-4-arylazo-3-methyl-1-phenyl-pyrazoles (3a-3e). The second step; (2a-2e) and (3a-3e) compounds were diazotised again and were coupled with ethyl benzoyl acetate. Later, they were reacted with hydrazine mono hydrate and phenyl hydrazine to give corresponding 4-(4'-arylazo-3'-methyl-1'-H-pyrazol-5-ylazo)?3?phenyl-1H?pyrazol-5-one (4a-4e), 4-(4'-arylazo-3'-methyl-1'-H-pyrazol-5-ylazo)?1,3-diphenyl?pyrazol-5-one (5a-5e), 4-(4'-arylazo-3'-methyl-1'-phenyl-pyrazol-5-ylazo)?3?phenyl-1H?pyrazol-5-one (6a-6e) and 4-(4'-arylazo-3'-methyl-1'-phenyl-pyrazol-5-ylazo)?1,3?diphenyl pyrazol-5-one (7a-7e). The synthesized disazo dyes were characterized by elemental analysis and spectral methods. The effect of varying solvent upon the absorption ability of dyes substituted with electron-withdrawing and electron-donating groups was examined in detail.