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Investigation On Synthesis, Design And Characterization Of Red Fluorescence Porphyrins

Posted on:2004-06-06Degree:DoctorType:Dissertation
Country:ChinaCandidate:J X SongFull Text:PDF
GTID:1101360122966970Subject:Applied Chemistry
Abstract/Summary:PDF Full Text Request
In order to study the synthetic methods and optoelectronic properties of porphyrins, three types of target molecules were designed and synthesized. i.e., meso-substituted porphyrins, β - pyrrolic substituted porphyrins , and both meso- and β -pyrrolic substituted porphyrins; we investigated the spectral properties of all the synthesized porphyrins; we also investigated the luminance of the red organic electroluminescence devices which constructed by using porphyrins as dopant, that was doped at different concentrations(1.5, 2, 2.7, 5 wt%) within a Alq3 host layer; a new chemical selection method for red dyes was obtained by imitation the devices with porphyrins doped into Alqs in chloroform.The main contents are as follows: 1. porphyrins' synthesis20 porphyrins,i.e.,2,7,12,17-tetramethyl-3,8,13,18-tetraeth ylporphyrin(TMTE,l), 2,7,12,17-tetramethyl-3,8,13,18-tetraethylporphyrin Zinc(II)(TMTEZn,2), Octaethylporphyrin(OEP,3), Octaethylporphyrin Zinc (OEPZn,4), meso-5,10,15,2,0-tetraphenylporphyrin(TPPH2,5), meso-5,10, 15,20-tetraphenylporphyrin Cobalt(II)(TPPCo,6), rneso-5,10,15,20-tetra-(p-hydroxylphenyl)porphyrin(Tp-OHPPH2,7), meso-5,10,15,20-tetra(p-chlorophenyl)porphyrin(Tp-C!PPH2,8), meso-5,10,15,20-tetra(p-methyl -oxylphenyl)porphyrin(Tp-OCH3PPH2,9), meso-5,10,15,20-tetra(3,4-dime thyloxylphenyl)porphyrin(T374-OCH3PPH2,10), meso-5,10,15,20-tetra(p-aminophenyl)porphyrin(TAPPH2,11), meso-5,10,15,20-tetraStyreneporph -yrin(TStPPH2,12), meso-5,10,15,20-tetraBiphenylporphyrin(TBPPH2,13), meso-5,10,15,20-tetra[pp-hydroxylbenzeneazophenyl]porphyrin [Tp-(p-OHBazo)PPH2,14], meso-5,10,15,20-tetra(p-Hydroxyl-o-Met -hylbenzeneazophenyl)porphyrin[Tp-(p-OH-o-CH3Bazo)PPH2,15], meso-5,10,15,20-tetra(p-Hydroxyl-m-Benzeneazo)phenylporphyrin(Tp-OH-m-BazoPPH2,16), meso-5,10,15,20-tetra(o-Hydroxyl-m-Benezeneazo)phen-ylporphyrin(To-OH-m-BazoPPH2,17), meso-5,10,15,20-tetra( P -Hydroxyl-naphtolazophenyl)porphyrin[Tp-( 3 -OHNazo)PPH2,18], 2,3,7,8,12,13, 17,18-Octamethyl-5,l 5-di(m-Bromophenyl)-10,20-diphenylporphyrin[(OM-B-m- BrP-BP)PH2,19], Porphyrin dimmer(DiPPH2,20) have been designed and synthesized. And eight substituted aromatic aldehyde have als -o been synthesized, they are p-phenylbenzaldehyde(21), p-aminobenzalde-hyde(22), (o-Hydroxyl-m-phenylazo)benzaldehyde(23), (p-Hydroxyl-m-ph enylazo)benzaldehyde(24), 4-(p-hydroxylbenzeneazo)benzaldehyde(25), 4-(o-Methyl-p-Hydroxylbenzeneazo)benzaldehyde(26), 4-( 3 -hydroxylnaphto -lazo)benzaldehyde(27), 4,4'-di(o-Hydroxyl-m-formoylbenzeneazo)bipheny -1(28). The compounds, with black label, are new or the synthetic methods are never reported before. All these compounds were characterized by 'HNMR, MS, UV-Vis and IR. Contents of this parts can be sorted as follow: (1) Study on the synthetic methods of porphyrinsAfter modification of Adler's reaction equipment,i.e.,adding a equipment which adsorbing water, bring the equilibrium to right, yields of porphyrins are improved, condensation of p-aminobenzaldehyde and pyrrole in propanoic acid directly, yield of porphyrin is 25%. Which is nine percent higher than reported (16%) before; Adding template to acetic acid, nitrogen purged, condensation of cassia aldehyde with pyrrole directly, then demetalled, tetrastyreneporphyrin (TStPPH2,12) was obtained in good yield, this kind of porphyrin is never reported before, it's a new synthetic method for porphyrins alike; adopting acetic acid as solvent and template added as well, condensation dipyrrole methane with benzaldehyde under dark and room temperature with stirring, porphyrin[(OM-Bm.BrP-BP)PH2,19]was obtained, this method can be used to synthesize this kind of porphyrin; a series of azoporphyrin were synthesized by condensing azoaldehyde and pyrrole in acetic acid, acetic acid is an ideal medium for azoporphyrins' synthesis; coupling of 5-hydroxylphenyl-10,15,20-trisphenylporphyrin with biphenylenebisazo salt at base solution, porphyrin dimer(DiPPH2,20) was obtained, which expanding the area of coupling reaction between diazo saltand phenols.(2) Study on the syn...
Keywords/Search Tags:Porphyrins, Design, Synthesis, Characterization, Doping Red Fluorescence, Spectra, Device, Imitation
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