螺[二苯并[a,j]氧杂蒽-14,9'-芴]的合成及性质  

Synthesis and Properties of Spiro[dibenzo[a,j]xanthene-14,9'-fluorene]

作　　者：陈木子[1] 尤永芝 张勇 李海燕[1] 方魏[1] 

机构地区：[1]苏州大学分析测试中心,苏州215123 [2]河南化工技师学院化学系,开封475002

出　　处：《高等学校化学学报》2014年第1期63-67,共5页Chemical Journal of Chinese Universities

摘　　要：芴酮与2-萘酚在硫酸和3-巯基丙酸的作用下反应得到化合物螺[二苯并[a,j]氧杂蒽-14,9'-芴].采用核磁共振、质谱、红外光谱和元素分析等对该化合物进行了表征,并通过X射线衍射法测得了其晶体结构,确定该化合物是通过二苯并[a,j]氧杂蒽中的含氧六元杂环和芴中的五元环共用一个碳原子形成一个螺环.利用荧光光谱和热分析等手段对该化合物的性质进行了研究,结果表明其最大荧光发射峰为366 nm,熔点为297℃,热分解温度为329℃,具有较高的热稳定性.Spiro[ fluorene-9,9＇-xanthene] （SFX） and its derivatives as the unit of organic optoelectronic ma- terials have attracted much attention due to their promising thermal and photophysieal properties. By tuning the conjugated degree and the steric of SFX, we designed a novel compound spiro[ dibenzo[ a,jl xanthene-14,9＇- fluorenel and anticipated that it would have better performance than SFX. The reaction of 9H-fluoren-9-one and naphthalen-2-ol under the conditions of sulfuric acid and 3-mercaptopropanoic acid gave the target compound spiro[ dibenzo[ a,j] xanthene-14,9＇-fluorenel. The compound was eharacterized by NMR, MS, IR spectra, elemental analysis and X-ray structural determination. The crystal data of the compound showed that a spiro ring was formed through the six-membered heterocyclic ring in dibenzo [ a, j] xanthene sharing one carbon atom with the five-membered ring in fluorene. The photophysical and thermal properties were investigated by UV-Vis absorption, photoluminescenee spectra, thermogravimetric analysis （TGA） and differential scanning calorimetry （DSC）. The maximum emission wavelength of the compound was found at 366 nm, and it showed a high thermal stability with a melting point of 297 ℃ and a decomposition temperature of 329 ℃. The results indicated that spiro[ dibenzo[ a,j] xanthene-14,9＇-fluorene ] could be used in the organic optoelectronic polymers to enhance their performance.

关 键 词：螺环 氧杂蒽 芴 晶体结构 

分 类 号：O621.3[理学—有机化学]