基于光致变色的联茚满烯二酮衍生物的新型光调控磁性的分子基磁体的合成及性能

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分子基磁性材料,可用于信息存储、磁成像、光磁开关等.因此,分子基磁体设计与合成一直是当今科学研究的热门课题.受分子基磁体的启发,本研究合成了新型光调控磁性的分子基磁体含有2-硝基丙烷自由基和2,2,6,6-四甲基-1-氧基哌啶(TEMPO)自由基的联茚满烯二酮衍生物4.化合物4的合成方法为,以光致变色的7,7’-二甲基-3,3’-二乙基-3,3’-二羟基-2,2’-二茚叉基-1,1’-二酮(1)为起始原料,经过溴代反应,得到7,7’-二(溴代甲基)-3,3’-二乙基-3,3’-二羟基-2,2’-二茚叉基-1,1’-二酮(2).化合物2和2-硝基丙烷在乙醇钠的乙醇溶液中反应得到含有2-硝基丙烷自由基和醛基的联茚满烯二酮衍生物3.根据1H NMR,MS和元素分析对化合物3的结构分析表明,2-硝基丙烷基团和化合物3苯环上的亚甲基相连.对化合物3的1H NMR和ESR波谱进一步的分析表明2-硝基丙烷基团上存在单电子自旋.在化合物3的基础上,稳定的氮氧自由基TEMPO被成功地引入光致变色的联茚满烯二酮衍生物的苯环上得化合物4.对化合物2,3和4光照前后的性质变化进行了研究.固态化合物2,3和4光照下皆可发生光致变色;固态化合物2光照后可测得ESR波谱;固态化合物3和4光照前后皆可测得ESR波谱,且光照前后ESR波谱发生变化.磁化率测试表明,固态化合物4光照前后皆具有反铁磁性,且光照后反铁磁相互作用增强.测试结果表明固态化合物3和4光照后有两个或三个自旋中心,分别是2-硝基丙烷或TEMPO自由基以及光照产生的来自于联茚满烯二酮的羰基上的自由基.固态化合物4的颜色和磁性可用光调控. Molecular-based magnetic materials can be used for information storage, magnetic imaging, magneto-optic switches, etc. Therefore, the design and synthesis of molecular-based magnets has been a hot topic in current scientific research.Inspired by molecular-based magnets, a new type of light- Of a molecular-based magnet contains a 2-nitropropane derivative and a biindane-dione derivative 4 of 2,2,6,6-tetramethyl-1-oxypiperidine (TEMPO) The synthesis method is that photochromic 7,7’-dimethyl-3,3’-diethyl-3,3’-dihydroxy-2,2’-diindenylidene-1,1’- The diketone (1) is used as a starting material to give 7,7’-bis (bromomethyl) -3,3’-diethyl-3,3’-dihydroxy-2,2 ’ -dindenylidene-1,1’-dione (2). Compound 2 and 2-nitropropane were reacted in sodium ethoxide in ethanol to obtain a biindane containing 2-nitropropane radical and aldehyde group Dione derivatives 3. Structural analysis of compound 3 according to 1H NMR, MS and elemental analysis showed that the 2-nitropropane group was linked to the methylene group on the benzene ring of compound 3. The 1H NMR and ESR spectra of compound 3 Further analysis showed that there was a single electron spin on the 2-nitropropane group. On the basis of compound 3, Nitroxide radical TEMPO was successfully introduced into the benzene ring of the photochromic biindane-dione derivative to obtain the compound 4. The changes of the properties before and after the illumination of the compounds 2, 3 and 4 were studied.Solid compound 2, ESR spectra were obtained after illumination of solid compound 2 and ESR spectra both before and after illumination of solid compounds 3 and 4. The magnetic susceptibility tests showed that ESR spectra of solid compounds 2 and 3 were changed before and after light irradiation, The solid-state compounds 4 were both antiferromagnetic before and after light irradiation and the antiferromagnetic interaction was enhanced after light irradiation.The results show that there are two or three spin centers after solid-state compounds 3 and 4, which are 2-nitropropane or TEMPO Free radicals and free radicals generated by light from the carbonyl group of the indanylene dione The color and magnetism of the solid compound 4 can be regulated with light.
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