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The Synthesis And Luminescent Properties Research Of Novel β-pyrrolic Substituted Triphenylaminoporphyrins

Posted on:2009-06-15Degree:MasterType:Thesis
Country:ChinaCandidate:L G WangFull Text:PDF
GTID:2121360272992287Subject:Organic Chemistry
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The aim of this thesis was to study on the synthetic methodology and spectral properties of porphyrins, so we synthesized two kinds ofβ-pyrrolic substituted porphyrins: 2-(4-N,N-diphenyl)phenyl-3,7,8,17,18-pentamethylporphyrin andβ-3,8,13,18-tetramethyl- 2,7,12,17-tetra(4-N,N-diphenyl)phenylporphyrin. The spectral properties of those porphyrins were resarched. 3,4-disubstituted pyrrole is an important intermediate ofβ-pyrrolic substituted porphyrins.We researched their synthetic methodology,Barton-Zard reaction. The main contents of this thesis are as follows:1. The synthetic methodology of 3,4-disubstituted pyrrole andβ-pyrrolic substituted porphyrin was briefly introduced and the development of the Barton-Zard reaction was sressed.2. Six representative new 3,4-disubstituted pyrroles, ethyl-3-(4-N,N-diphenyl)phenyl -4-methyl-pyrrole-2-carboxylate and alkyl-8-tosyl-quinolino[5,6,c]pyrrole-2-carboxylates respectively were synthesized and structurally characterized.3. An improvement, which adopt readily available inorganic base potassium carbonate instead of the organic base, 1,8-diazabicyclo[5.4.0]undec-7-ene(DBU)and easily hydrolyzed potassium tert-butoxide to the Barton-Zard reaction was employed during the synthesis of all the desired 3,4-disubstituted pyrroles.The improved method was flexible and convenient to operate.4. The symmetrical porphyrinβ-3,8,13,18-tetramethyl-2,7,12,17-tetra(4-N,N-diphenyl) phenylporphyrin, was synthesized from ethyl-3-(4-N,N-diphenyl) phenyl-4-methylpyrrole-2- carboxylate through pyrrole self-polymerization. And another unsymmetrical porphyrin,2-(4-N,N-diphenyl)phenyl-3,7,8,17,18-pentamethylporphyrin , was synthesized from 3- (4-N,N-diphenyl)phenyl-4-methylpyrrole through"3+1"approach.5. The spectral properties of 2-(4-N,N-diphenyl)phenyl-3,7,8,17,18-pentamethyl porphyrin andβ-3,8,13,18-tetramethyl-2,7,12,17-tetra(4-N,N-diphenyl) phenylporphyrin were researched and the effect of the porphyrins'structures to spectral properties was discussed.
Keywords/Search Tags:Barton-Zard reaction, 3,4-disubstituted pyrroles, β-pyrrolic substituted porphyrins, Synthesis, Spectral properties
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