碘代1,5-戊二酮的合成及光物理性质OA
Syntheses and Photophysical Properties of 2,4-diiodo-1,5-di(thiophen-2-yl)-3-(p-tolyl)pentane-1,5-dione
以2-乙酰噻吩和对甲基苯甲醛为原料,经羟醛缩合、迈克尔加成及碘仿反应,以较高产率制备了碘代1,5-戊二酮,并采用核磁共振氢谱、傅里叶变换红外光谱、熔点和紫外可见吸收光谱对该目标化合物及其中间体的结构和光谱性质进行了测定.研究发现:在碱性条件下,1,5-戊二酮与碘主要发生碘仿反应,取代位置在羰基邻位的亚甲基上,分别在两个亚甲基上引入了一个碘原子.紫外可见吸收光谱分析表明,与 1,5-戊二酮相比,碘代 1,5-戊二酮的最大吸收波长红移了29 nm.这表明碘原子的引入显著扩大了1,5-戊二酮的共轭体系,降低了 π-π*跃迁的能垒.
Using 2-acetylthiophene and p-methylbenzaldehyde as starting materials,iodinated 1,5-pentanedione was synthesized with high yield via aldol condensation,Michael addition,and iodoform reaction.The structures and spectral properties of the target compound and its intermedi-ates were analyzed by 1H NMR,Fourier transform infrared spectroscopy(FT-IR),melting point,and UV-Vis absorption spectroscopy.The study found that under alkaline conditions,1,5-pentanedione mainly undergoes α-H nucleophilic substitution with iodine at room temperature,occur-ring at the methylene groups adjacent to the carbonyl groups,thereby introducing one iodine atom on each methylene group.UV-Vis spectral a-nalysis revealed that compared with 1,5-pentanedione,the maximum absorption wavelength of iodinated 1,5-pentanedione exhibits a red shift of 29 nm.This indicates that the introduction of iodine atoms significantly expands the conjugated system of 1,5-pentanedione,lowering the energy barrier for the π-π* transition.
杨德龙;田洋;杨德蓉;朱瑾瑶;刘意
贵州师范学院 化学与材料学院,贵州 贵阳 550018贵州师范学院 化学与材料学院,贵州 贵阳 550018贵州师范学院 化学与材料学院,贵州 贵阳 550018贵州师范学院 化学与材料学院,贵州 贵阳 550018贵州师范学院 化学与材料学院,贵州 贵阳 550018
化学化工
1,5-戊二酮碘仿反应结构表征光谱性质
1,5-di(thiophen-2-yl)-3-(p-tolyl)pentane-1,5-dioneIodoform ReactionStructural CharacterizationPhotophysical Properties
《云南化工》 2026 (8)
23-26,4
贵州师范学院2024年国家级大学生创新创业训练计划(2024142230470).
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