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Synthesis, spectroscopic properties, and tautomerism of mono-meso-substituted octamethylporphyrins
作者姓名:LI  Ming YAO  Yi-Ming ZOU  Jian-Zhong XU  Zheng YOU  Xiao-ZengCoordination Chemistry Institute  Coordination Chemistry State Key Laboratory  Nanjing University  Nanjing  Jiangsu  China
作者单位:LI,Ming YAO,Yi-Ming ZOU,Jian-Zhong XU,Zheng YOU,Xiao-ZengCoordination Chemistry Institute,Coordination Chemistry State Key Laboratory,Nanjing University,Nanjing,Jiangsu 210008,China
基金项目:Project supported by the National Natural Science Foundation of China and a key research project from the State Science and Technology Commission.
摘    要:The synthesis spectroscopic properties and tautomerism of four novel mono-meso substituted(R)-octamethylporphyrins (R=o-hydroxybenzyl, p-aminobenzyl, 4-pyridinyl, and ferro-cenyl) were investigated. It was found that the porphyrins 2, 3 could be directly prepared in good yields via the coupling reaction of salicylaldehyde and p-aminobenzyl aldehyde with octamethyl-l',8'-dideoxy-ac-biladiene dihydrobromide, respectively. The free energy of activation (G) of the tautomerism of the porphyrins was calculated and interpreted in terms of electronic and steric nature. In contrast with 2-substituted-5,10,15,20-tetraphenylporphyrins, the substituents in meso position do not change the relative amount of two tautomers a and 6.


Synthesis, spectroscopic properties, and tautomerism of mono-meso-substituted octamethylporphyrins
LI,Ming YAO,Yi-Ming ZOU,Jian-Zhong XU,Zheng YOU,Xiao-ZengCoordination Chemistry Institute,Coordination Chemistry State Key Laboratory,Nanjing University,Nanjing,Jiangsu ,China.Synthesis, spectroscopic properties, and tautomerism of mono-meso-substituted octamethylporphyrins[J].Chinese Journal of Chemistry,1994,12(3):237-242.
Authors:LI  Ming YAO  Yi-Ming ZOU  Jian-Zhong XU  Zheng YOU  Xiao-ZengCoordination Chemistry Institute  Coordination Chemistry State Key Laboratory  Nanjing University  Nanjing  Jiangsu  China
Institution:LI,Ming YAO,Yi-Ming ZOU,Jian-Zhong XU,Zheng YOU,Xiao-ZengCoordination Chemistry Institute,Coordination Chemistry State Key Laboratory,Nanjing University,Nanjing,Jiangsu 210008,China
Abstract:The synthesis spectroscopic properties and tautomerism of four novel mono-meso substituted(R)-octamethylporphyrins (R=o-hydroxybenzyl, p-aminobenzyl, 4-pyridinyl, and ferro-cenyl) were investigated. It was found that the porphyrins 2, 3 could be directly prepared in good yields via the coupling reaction of salicylaldehyde and p-aminobenzyl aldehyde with octamethyl-l',8'-dideoxy-ac-biladiene dihydrobromide, respectively. The free energy of activation (G) of the tautomerism of the porphyrins was calculated and interpreted in terms of electronic and steric nature. In contrast with 2-substituted-5,10,15,20-tetraphenylporphyrins, the substituents in meso position do not change the relative amount of two tautomers a and 6.
Keywords:Mono-meso-substituted octamethylporphyrins  spectroscopy  tautomerisra  
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