几种取代胡椒醛缩合不对称卟啉化合物的合成及结构表征

Synthesis and Characterization of Novel Unsymmetrical Porphyrins Condensed from Substituted Piperonal

利用微波加热法,以6-硝基胡椒醛、两种R取代苯甲醛(R=H,Cl)、吡咯为原料,在丙酸中缩合,合成了两种新的不对称卟啉化合物5-(2-硝基-4,5-亚甲二氧基)苯基-10,15,20-三苯基卟啉(2)和5-(2-硝基-4,5-亚甲二氧基)苯基-10,15,20-三对氯苯基卟啉(3).将2和3还原得到了化合物5-(2-氨基-4,5-亚甲二氧基)苯基-10,15,20-三苯基卟啉(4)和5-(2-氨基-4,5-亚甲二氧基)苯基-10,15,20-三对氯苯基卟啉(5).新化合物结构分别经UV-Vis,IR,1HNMR及元素分析所证实.荧光测试表明,几个化合物都有比较好的荧光强度,且氨基取代化合物的荧光强度比相应的硝基化合物的大.

Two unsymmetrical porphyrins of 5-(2-nitro-4,5-methylenedioxy)phenyl-10,15,20-triphenylporphyrin (2) and 5-(2-nitro-4,5-methylenedioxy)phenyl-10,15,20-tri(p-chlorophenyl)-porphyrin (3) were prepared using microwave irradiation. The reduction of 2 and 3 gave 5-(2-amino-4,5-methylenedioxy)phenyl-10,15,20-triphenylporphyrin (4) and 5-(2-amino-4,5-methylenedioxy)phenyl-10,15,20-tri(p-chlorophenyl)porphyrin (5). These novel porphyrins have been confirmed by UV-Vis, IR, H-1 NMR spectra and elemental analysis.