Fourier Transform Infared and Proton Nuclear Magnetic Resonance Analysis of Sampled Quinolinediones and Effects of Mordants on their Dyestuff Properties

ABSTRACT; Structural identification and new application of synthesized compounds have been a viable pursuit in organic chemistry. In this work, Fourier Transform Infared (FT-IR) and Proton Nuclear Magnetic Resonance (Hnmr) spectroscopies were used to measure quinolinediones. FT-IR and Hnmr provided useful ways for identification of the compounds. Characteristic Infrared absorptions for quinolinediones such as 750 cm-1(C-X); 1215 cm-1 (C-N); 1650 cm-1 (C=O), among others, were observed and characteristic proton-proton coupling constants for quinolinediones, 4.7/7.9, among others and chemical shifts were observed. Quinolinediones produced excellent colours on cotton fabrics, food, petroleum jelly and illicit gin, with most enhanced binding when used with FeSO4 and K2Cr2O7 mordants in both light and wash fastness. Alum also showed good fastness to mild soap. Varied excellent colours were imparted on the quinolinediones: 6,7-dibromo-5,8-quinolinedione imparted lemon green colour on starchy food; orange colour on petroleum jelly and brown colour on illicit gin while 6,7-dichloro-5,8-quinolinedione imparted brownish milk colour on starchy food and light yellow colour on petroleum jelly and illicit gin. FT-IR and Hnmr are therefore recommended as being sufficient for structural elucidation of quinolinediones and their derivatives. Quinolinediones are also recommended as good dyes and colourants, which will be consequent upon further studies about the toxicological effects.

摘要：合成化合物的结构鉴定与新应用探索，一直是有机化学领域的重要研究课题。本研究采用傅里叶变换红外光谱（Fourier Transform Infrared, FT-IR）与质子核磁共振波谱（Proton Nuclear Magnetic Resonance, Hnmr）对喹啉二酮类化合物进行表征。FT-IR与Hnmr可为该类化合物的结构鉴定提供有效手段。实验观测到喹啉二酮类化合物的特征红外吸收峰，例如750 cm⁻¹处的C-X键吸收、1215 cm⁻¹处的C-N键吸收、1650 cm⁻¹处的C=O键吸收等；同时观测到该类化合物的特征质子-质子耦合常数（如4.7/7.9）及化学位移。喹啉二酮类化合物可在棉织物、食品、凡士林及非法私酿杜松子酒上呈现优异的着色效果；当其与硫酸亚铁（FeSO₄）和重铬酸钾（K₂Cr₂O₇）作为媒染剂复配使用时，样品的耐光性与耐洗性均得到显著提升。以明矾作为媒染剂时，着色样品也可获得良好的温和皂洗牢度。不同的喹啉二酮类化合物可呈现各异的优异着色效果：6,7-二溴-5,8-喹啉二酮可在淀粉类食品上呈现柠檬绿色、在凡士林中呈现橙色、在非法私酿杜松子酒中呈现棕色；而6,7-二氯-5,8-喹啉二酮可在淀粉类食品上呈现棕奶色、在凡士林与非法私酿杜松子酒中呈现浅黄色。因此，FT-IR与Hnmr可作为喹啉二酮类化合物及其衍生物结构解析的有效表征手段。喹啉二酮类化合物亦可作为优质染料与着色剂，其实际应用潜力仍需通过后续毒理学效应研究进一步验证。