Meso site arylamino monosubstituted porphyrin derivative and preparation method thereof

An arylamine-based mono- and derivative technology, which is applied in the field of meso-position arylamine-based mono-substituted porphyrin derivatives and the preparation thereof, can solve the problems of less research on compound synthesis, many porphyrin synthesis steps, high difficulty and the like, and achieves pollution. less, better reaction selectivity and higher yield

Active Publication Date: 2015-06-24
JIANGSU RUIDA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Generally, there are many steps and difficulties in the synthesis of asymmetric meso-position monosubstituted porphyrins, and there are few studies on the synthesis of such compounds.

Method used

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  • Meso site arylamino monosubstituted porphyrin derivative and preparation method thereof
  • Meso site arylamino monosubstituted porphyrin derivative and preparation method thereof
  • Meso site arylamino monosubstituted porphyrin derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] 4-N,N-Dimethylaminobenzaldehyde (1mmol) and dibromo-1,19-dideoxy-3,8,12,17-tetraethyl-2,7,13,18-tetramethyl Add biladien-a, c (1mmol) into a 250mL three-necked flask, and add ethanol (100mL) to dissolve. The solution was heated to reflux (78-82°C) under argon protection. p-Toluenesulfonic acid (2.5 g) was dissolved in ethanol (10 mL) and added slowly to the reaction mixture over 18 hours. The reaction mixture was then continued for up to 48 hours. After the reactant was cooled to room temperature, the solvent was removed under reduced pressure. The residue was dissolved in 200 mL DCM and washed with saturated NaHCO 3 The solution and distilled water were washed twice, and the aqueous layer was removed. The solvent was evaporated under reduced pressure for chromatographic separation, and the product 5-(4-N,N-dimethyl)phenyl-13,17-diethyl-2,3,7,8 was obtained after recrystallization from methanol and chloroform , 12,18-Hexamethylporphyrin (1a). Yield: 42.1%. Meltin...

Embodiment 2

[0028] Synthesis of 5-(4-carbazolyl)phenyl-13,17-diethyl-2,3,7,8,12,18-hexamethylporphyrin (1b): 4-carbazolylbenzaldehyde (1mmol) and dibromo-1,19-dideoxy-3,8,12,17-tetraethyl-2,7,13,18-tetramethylbiladien-a,c (1mmol) into a 250mL three-necked flask, And add ethanol (100mL) to dissolve, other methods are the same as Example 1, productive rate: 29.4%. Melting point: >250℃; Esi-MS: calcd for C 48 h 46 N 5 692.38, found: 692.38 (M+H + )( Figure 4 ); 1 H-NMR (600MHz, CDCl 3 )δ10.20(2H, s), 10.00(1H, s), 8.31(4H, m), 7.95(2H, d), 7.77(2H, d), 7.64(2H, m), 7.45(2H, d ), 4.10(4H, q), 3.68(6H, s), 3.61(6H, s), 2.71(6H, s), 1.91(6H, t), -3.12(1H, s), -3.26(1H, s)( Figure 5 ; UV-vis: 403nm, 503nm, 536nm, 570nm, 625nm ( Image 6 ).

Embodiment 3

[0030] 5-(4-(3,6-di-tert-butyl)carbazolyl)phenyl-13,17-diethyl-2,3,7,8,12,18-hexamethylporphyrin (1c) Synthesis of: 4-(3,6-di-tert-butylcarbazolyl)benzaldehyde (1mmol) and dibromo-1,19-dideoxy-3,8,12,17-tetraethyl-2,7, 13,18-Tetramethyl biladien-a,c (1 mmol) was added into a 250 mL three-necked flask, and ethanol (100 mL) was added to dissolve it. The other methods were the same as in Example 1, and the yield was 32.5%. Melting point: >250℃; Esi-MS: calcd for C 56 h 62 N 5 804.5005, found: 804.5026 (M+H + )( Figure 7 ); 1 H-NMR (600MHz, CDCl 3 )δ10.20(2H, s), 9.99(1H, s), 8.32(2H, s), 8.19(2H, d), 7.89(2H, d), 7.71(4H, d), 4.10(4H, q ), 3.67(6H, s), 3.59(6H, s), 2.66(6H, s), 1.91(6H, t), 1.60(18H, s), -3.14(1H, s), -3.26(1H, s)( Figure 8 ); UV-vis: 403nm, 501nm, 536nm, 570nm, 622nm ( Figure 9 ).

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Abstract

The invention discloses a meso site arylamino monosubstituted porphyrin derivative and a preparation method thereof. The meso site arylamino monosubstituted porphyrin derivative comprises compounds 1a, 1b and 1c. The preparation method comprises the following steps: under argon protection, aromatic aldehyde and dibromo-1,19-dideoxy-3,8,12,17-tetraethyl-2,7,13,18-tetramethyl (biladien-a, c) generate the meso site arylamino monosubstituted porphyrin derivative under the catalytic action of p-toluenesulfonic acid. The porphyrin derivative provided by the invention can be used as an electron donor and has wide application prospects in the aspects of organic field effect tubes, molecular antennas, photo-energy converters, photoelectric conversion materials, molecular switches, molecular wires, organic solar cells, organic electroluminescent materials, nonlinear optical materials, molecular recognition, medicines and the like. The preparation method has the advantages of convenient and economical operation, good reaction selectivity, high yield, little pollution, and the like.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and in particular relates to a meso-position aromatic amino monosubstituted porphyrin derivative and a preparation method thereof. Background technique [0002] Porphyrin compounds have many unique photoelectric properties, good light and thermal stability, and have a large molar absorptivity in the visible light range, so they have been widely used in biochemistry, medicine, analytical chemistry, photocatalysis, and material science. It has received extensive attention and application. In recent years, using the unique electronic structure and photoelectric properties of porphyrin molecules, the design and synthesis of photoelectric functional materials and the development of photoelectric devices have become very active research fields at home and abroad. In terms of energy transfer, porphyrin molecules, as light-absorbing units in model compounds, can realize light-induced ...

Claims

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Application Information

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IPC IPC(8): C07D487/22
CPCC07D487/22
Inventor 徐海军沙秋月郭颖昕陈继超
Owner JIANGSU RUIDA TECH CO LTD
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