Purple red solid meso tetra (o-alkoxyphenyl) porphyrin cobalt (meso-t (2-rop) PCO) / tetra (n, n-diphenyl-p-amino) phenyl porphyrin (tdpatph2)

meso- Four ( O-alkoxyphenyl ) Porphyrin cobalt (meso-T(2-ROP)PCo)(3) Introduction of purple solid products

This paper synthesized meso- Four ( O-alkoxyphenyl ) Porphyrin cobalt complex 10 individual , Among them, there are no new compounds reported in the literature 8 individual , The crystal or solid of this series of complexes , Its structure was confirmed by spectral method , use DSC and PM The liquid crystal properties of these complexes were studied , Find out 6 The complexes are liquid crystalline . The synthetic route of the complex is as follows :

 

A return condensing pipe is installed at the 、 Constant pressure dropping funnel 25mL In a three necked bottle , Add people 0.02mmolmeso-T(2-ROP)PH2,5mLCHCl, Magnetic stirring dissolves solid matter , Heating reflux , Dripping

0.2mmol Methanol saturated solution of cobalt acetate , use TLC Monitor the reaction endpoint , After the spots of raw materials disappear ( about 1~2h), Stop heating . After the reaction , Evaporate the solvent in a water bath , The viscous substance dissolves in CHCl3 Post neutral Al2O3 Column separation and purification ,CHCl3 As eluent , Collect a thick Ribbon , Evaporate the solvent in a water bath , And pump it dry . Then use petroleum ether / Recrystallization of methanol mixed solvent and long-time freezing in ice salt bath , have to meso- Four ( O-alkoxyphenyl ) Porphyrin cobalt (meso-T(2-ROP)PCo)(3) Purplish red solid product 10 individual .

  Four (N,N- Diphenyl p-amino ) Phenylporphyrin (TDPATPPH2) Introduction to

In recent years , Porphyrin compounds as materials for red light-emitting organic light-emitting devices are attracting great interest . Such as tetraphenyl porphyrin (TPPH2)、 Tetraphenyl zinc porphyrin (ZnTPP)[2]、 Octaethyl palladium porphyrin (PaOEP)[3] And chlorin (TPC)[4 Preparation of organic light emitting devices by doping (OLED) All get red light , And in the red light OLED Has made a major breakthrough in the development of . But the porphyrin red light currently used OLED There are still problems such as high driving voltage , Bimolecular coupling fluorescence quenching , The long lifetime of electron excitation leads to the supersaturation of red light , Low brightness . Therefore, it is necessary to study the red luminescent materials 、 Polyarylamine compounds have low ionization energy , It is easy to lose electrons and form holes , It is a good hole transport material , It has been applied to the preparation of organic electroluminescent devices . Whereas polyarylamine compounds and porphyrin compounds are in OLED Application of , We think , The two hydrogen atoms on the amino group in tetraaminophenyl porphyrin are replaced by benzene ring , Polyarylamine compounds and porphyrin rings are combined in - Together , Make molecules more conjugated , More electronic cushioning , Energy transfer is easier , It will be possible to obtain better OLED material . So , We have designed and synthesized the polyarylamine porphyrin tetra (N,N- Diphenyl p-amino ) Phenylporphyrin (TDPAPPH). The UV and fluorescence spectra of the compound were compared with TPPH: and TAPPH.[0_~8] The UV and fluorescence spectra were compared . These compounds have not been reported in the literature .

TDPAPPH2 Synthesis

theory . To synthesize the target molecule TDPAPPH2 Yes 2 Feasible routes :(1) From four ( P-aminophenyl ) Porphyrins start , the Ullmann Reaction with iodobenzene , Replace the hydrogen in the amino group with benzene ring ;(2) By right -N,N- Direct synthesis of porphyrins from diphenylaminobenzaldehyde . Route (1) It is difficult to synthesize tetraaminophenyl porphyrin , At the same time, it is easy to oxidize under high temperature , And the amount of hydrogen in the amino group is too large . It is difficult for hydrogen to be completely replaced by benzene ring in the reaction , Not getting the target product , Therefore, the route is adopted (2).TDPAPPH2 The synthetic route of is shown in Scheme1.

 TDPAPPH2 The spectral properties of

   This article comes from Xiaobian axc. Xi'an Qiyue biology Co., Ltd ”2022.02.14