Synthesis and Characterization of meso-5,15-Bis(p-aminophenyl)-2,3,7,8,12,13,17,18-octamethyl-porphyrin and Its Metal Derivatives
ZHU Bao-KU, WEI Xiu-Zhen, XU You-Yi, XU Zhi-Kang
2003, 24(11):
1945-1949.
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An important compound of 3,3′,4,4′-tetramethyl-2,2′-dipyrrolylmethane (TMDPM, 6) was synthesized through multi-step-reaction starting from 3-methyl-2,4-dipentadione.Therein, the reaction for converting 3,3′,4,4′-tetramethyl-2,2′-dipyrrolylmethane-5,5′-dicarbonate(5) to TMDPM waSImproved by substituting hydrazine witHEthanolamine as decarboxylation agent.The synthesis of meso-15,15-bis-phenyl-porphyrin by dipyrrolylmethane procedure waSInvestigated.It was found that p-toluenesulfonic acid was the efficient catalyst for condensation of compound 6 with nitrobenzaldehyde to porphyrinogen (7), and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone(DDQ) was effective reagent for oxidizing of compound 7 to nitroporphyrin.After the hydrogenation of nitro-groups by SnCl2/concentrated HCl system to amino-groups, the extraction of the resulted aminoporphyrin by solid-mixture/chloroform process conducted better effects than aqueous-mixture/chloroform process.Following the methods aforesaid, several new porphyrin compoundSIncluding 5,15-bis(4-nitrophenyl)-2,3,7,8,12,13,17,18-octamethyl-porphyrin(BNPP, 8),5,15-bis(4-aminophenyl)-2,3,7,8,12,13,17,18-octamethyl-porphyrin(BAPP, 9) and metal-BAPP were synthesized.Their structures and absorption properties were characterized as well.
