新型4-{4,5-二[(E)-苯乙烯]-1H-咪唑-2-基}苯甲醛共价键连单羟基四苯基卟啉化合物的合成及其分子内能量转移性能

Synthesis and Intramolecular Energy Transfer Properties of Novel 4-{ 4,5-di[( E)-styryl]-1H-imidazol-2-yl) benzaldehyde Covalently Bonded Monohydroxy Tetraphenylporphyrin Compound

以2,3-丁二酮为原料,依次与苯甲醛和对苯二甲醛经缩合反应制得4-{4,5-二[(E)-苯乙烯]-1H-咪唑-2-基)苯甲醛}(2);以对二氯苄作为连接链,2与其经取代反应制得4-{1-[4-(氯甲基)苄基]-4,5-二[(E)-苯乙烯]-1H-咪唑-2-基}苯甲醛(3);3与单羟基四苯基卟啉(4)连接合成了4-{4,5-二[(E)-苯乙烯]-1H-咪唑-2-基}苯甲醛共价键连单羟基四苯基卟啉化合物(5),其中2,3和5为新化合物,其结构经1H NMR,MS和元素分析表征。用荧光光谱研究了5中基团3与基团4之间的能量转移过程。结果表明,当激发取代基团3时,能量能够从基团3转移至基团4上。

4-{ 4,5-Di[（ E）-styryl]-1H-imidazol-2-yl} benzaldehyde（ 2） was prepared by condensation of the 2,3-butanedione with benzaldehyde,followed with 1,4-phthalaldehyde. 4-{ 1-[4-（ Chloromethyl） benzyl]-4,5-di[（ E）-styryl]-1H-imidazol-2-yl} benzaldehyde（ 3） was obtained by displacement reaction of 2 with p-dichlorobenzyl. 4-{ 4,5-Di [（ E）-styryl]-1H-imidazol-2-yl） benzaldehyde covalently bonded monohydroxy tetraphenylporphyrin compound（ 5） was synthesized by the reaction of3 with monohydroxy tetraphenylporphyrin（ 4）. 2,3 and 5 were novel compounds. The structures were characterized by1 H NMR,MS and elemental analysis. The fluorescence spectra of 3 ~ 5 were investigated and it was indicated that when excited at the absorption of 3 group,the energy could transfer to the porphyrin core in 5.