[Synthesis of 2-(2,5-dihydroxyphenyl)-tetraphenylporphrin and its structure identification].
2-(2,5-dihydroxyphenyl)-tetraphenylporphrin 1',2-(2,5-dihydroxyphenyl)-tetraphenylporphyrinato Cu (II)2', Ni(II)3' and Zn(II)4' were synthesized by direct reaction of 2-nitro-5,10,15,20-tetraphenylporphrin 1 or its metallic complexes 2, 3, 4 with hydroquinone under heating without solvent. The yields were about 81%, 71%, 61% and 40% respectively for 1', 2', 3' and 4'. Their structures were determined by 1H NMR, 2D NMR, IR, MS and UV-Vis spectra. It is shown that the hydroquinone connects with pyrrole ring through carbon-carbon bond, and is located in the same plane of porphyrin. One of the hydroxy group of hydroquinone is located in the deshield area of porphyrin and its proton shift occurs downfield at delta = 7.52. Another one is located in the shield area of meso benzene, and the proton shift occurs upfield at delta = 4.18. Also the 6 proton shift of hydroquinone occurs upfield at delta = 4.93.
Chen
Shi-qing
SQ
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, China.
Chen
Zhang-ping
ZP
Huang
Qi-mao
QM
Jiang
Zhong-xing
ZX
D003300:Copper / Q000737:chemistry; D008279:Magnetic Resonance Imaging; D009682:Magnetic Resonance Spectroscopy / Q000379:methods*; D008670:Metals / Q000737:chemistry*; D008956:Models, Chemical; D009532:Nickel / Q000737:chemistry; D011166:Porphyrins / Q000138:chemical synthesis* / Q000737:chemistry; D012997:Solvents / Q000737:chemistry; D013055:Spectrophotometry, Infrared / Q000379:methods; D015032:Zinc / Q000737:chemistry
D008670:Metals; D011166:Porphyrins; D012997:Solvents; D003300:Copper; D009532:Nickel; D015032:Zinc