CN106905326A - The synthetic method of dodecyloxy phenyl porphyrin benzamide hexane imines Qiao Lian perylene dihexyl binary compounds - Google Patents
The synthetic method of dodecyloxy phenyl porphyrin benzamide hexane imines Qiao Lian perylene dihexyl binary compounds Download PDFInfo
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Abstract
The invention discloses a kind of synthetic method of dodecyloxy phenyl porphyrin benzamide hexane imines Qiao Lian perylene dihexyl binary compounds.() is unilateral Jiang after perylene tetracarboxylic acid dianhydride is first hydrolyzed to be condensed get Dao perylene list acid anhydride dihexyl；(2) it is one porphyrin compound with amino side chain of main Material synthesis by one pot process porphyrin ester and then with 1,6 hexamethylene diamines；(3) there is acid amides and be synthesized to obtain target compound in imidazoles in the intermediate for obtaining above-mentioned two parts.The present invention has been designed and synthesized with alkoxyporphyrin as electron donor（Donor）, flexible oxyalkyl chain is pontic（Bridge）, the ester units of perylene list acid imide two are electron acceptor（Acceptor）The binary compound for having D B A type structures, this kind of compound can be applied in fields such as organic photovoltaic material, liquid crystal material, organic solar batteries, Organic Light Emitting Diodes as material.
Description
Technical field
Connect perylene dihexyl binary chemical combination the present invention relates to a kind of dodecyloxy phenyl porphyrin benzamide hexane imines bridge
The synthetic method of thing.
Background technology
Porphyrin quasi-molecule is a kind of compound with big pi-conjugated system, in having a plate-like of similar discotic liquid-crystalline molecules
The heart.Simultaneously porphyrin discotic mesogenic due to the interaction of π-π interorbitals in its aromatic proton, can in one-dimensional square self assembly heap
Columnar phase is accumulated into, so that electric charge carrier will be significantly larger than the migration along intercolumniation direction along the mobility of main direction.This
Outward, the discotic mesogenic of high degree of symmetry also has larger refractive index, and the feature such as transformation behavior wider and enthalpy change higher makes
The research for obtaining porphyrin liquid crystal has great significance.
Perylene diimide class discotic mesogenic material is the compound that a class has special condensed cyclic structure, with good light, heat
Stability and inoxidizability, while possess spectral absorption scope wider, and excellent optical such as high-fluorescence quantum yield
Matter.By in perylene core be in electron deficient system property, with electron affinity energy higher, this make perylene diimide analog derivative turn into one
Typical N-shaped organic semiconducting materials are planted, therefore has obtained widely studied in organic photovoltaic field.
The content of the invention
It is an object of the invention to provide dodecyloxy phenyl porphyrin benzamide hexane imines Qiao Lian perylene dihexyl binary
The synthetic method of compound.
Synthetic route of the present invention is divided into three below part：Part I is by 3,4,9,10- perylene tetracarboxylic acid dianhydride Tong Guo perylenes
Four own ester transition are condensed get Dao perylene list acid anhydride dihexyl by unilateral again；Part II be by one pot process porphyrin ester then with
1,6- hexamethylene diamines are one porphyrin compound with amino side chain of main Material synthesis；Part III is to obtain above-mentioned two parts
Intermediate dodecyloxy phenyl porphyrin benzamide hexane imines Qiao Lian perylene dihexyl dualizations are synthesized by acid amides
Compound.
The present invention has been designed and synthesized with alkoxyporphyrin as electron donor（Donor）, flexible oxyalkyl chain is pontic
（Bridge）, the ester units of perylene list acid imide two are electron acceptor（Acceptor）The binary compound for having D-B-A type structures, this
Class compound can be applied in organic photovoltaic material, liquid crystal material, organic solar batteries, Organic Light Emitting Diode as material
Deng field.
Brief description of the drawings
Fig. 1 is the structure of dodecyloxy phenyl porphyrin benzamide hexane imines Qiao Lian perylene dihexyl binary compounds
Formula.
Fig. 2 is the road for synthesizing dodecyloxy phenyl porphyrin benzamide hexane imines Qiao Lian perylene dihexyl binary compounds
Line chart.
Marked in figure：1- compounds 1,2- compounds 2,3- compounds 3,4- compounds 4,5- compounds 5,6- compounds
6。
Specific embodiment
Embodiment：
It is pure that chemical reagent and solvent used in embodiment are analysis.
(1) to dodecyloxy benzaldehyde（Compound 1）Synthesis：
By 2.44 grams of parahydroxyben-zaldehydes, 6.73 grams of bromododecanes and 5.52 grams of Anhydrous potassium carbonates, 20 milliliters are dissolved in through CaH2
Dry N,N-dimethylformamide solvent.Under nitrogen protection, it is heated to 80 DEG C and stirs 12 hours.Room temperature is cooled to, will be reacted
Liquid is poured into 100 milliliters of water, is extracted with 20 milliliters of dichloromethane, and organic layer, rotated evaporation are dried with anhydrous sodium sulfate
After instrument removes solvent, purified with 200-300 mesh silica gel column chromatography（Leacheate is dichloromethane：Petroleum ether volume ratio is 1:5-1:
2) weak yellow liquid i.e. compound 1, is obtained（5.75 grams, yield 98%）.bp >300℃, IR(KBr) νmax (cm-1):1610,
1380,1260, 841; 1H NMR (300 MHz, CDCl3) δ/ppm: 9.87(s, H), 7.68(t, J = 6.9 Hz,
2H), 6.89 (d, J = 8.4 Hz,2 H), 3.99 (t, J = 6.9 Hz, 2 H), 1.83-1.76 (m, J =
6.9 Hz, 4 H), 0.96-1.31 (m, J = 5.4 Hz, 10 H)。
(2) 5- para Toluic Acids carbomethoxy -10,15,20- three is to dodecyloxy phenyl porphyrin（Compound 2）Conjunction
Into：
By 1,1.20 grams of 5.88 g of compound to acyl group methyl benzoate and 1.85 grams of m-Nitrobenzoic Acids, 32 milliliters of diformazans are dissolved in
Benzole soln, 32 milliliters are added dropwise containing 1.91 grams of xylene solutions of pyrroles 10 minutes by constant pressure funnel, and 140 DEG C of heating is stirred
Mix 3.5 hours.Reaction terminates, and is cooled to room temperature, and 180 milliliters of absolute methanol is poured into reaction solution, and suction filtration after standing is obtained
Purple material, is purified with 200-300 mesh silica gel column chromatography（Leacheate is that dichloromethane/petroleum ether volume ratio is 1:2-1:1), use
Dichloromethane/absolute methanol volume ratio=1:1 recrystallization, obtains violet solid i.e. compound 2（2.3 grams, yield 32.7%）.Mp
125.1-126.2℃, IR(KBr) νmax (cm-1): 1720,1350,1240, 803; 1H NMR (400 MHz,
CDCl3) δ/ppm 8.90 (d, J = 6.0 Hz, 6H), 8.76 (d, J = 4.7 Hz, 2H), 8.44 (d, J =
8.0 Hz, 2H), 8.30 (d, J = 8.0 Hz, 2H), 8.16 -8.05 (m, 6H), 7.29 (d, J = 8.4
Hz, 6H), 4.15 (d, J = 5.6 Hz, 6H), 4.11 (s, 3H), 1.93 (m, 3H), 1.77 -1.54 (m,
12H), 1.51-1.35 (m, 12H), 1.06 (m 9H), 1.00 (t, J = 6.8 Hz, 9H), -2.74 (s,
2H)。
(3) 5- paraphenylene terephthalamides (6- amino-hexyls) -10,15,20- three is to dodecyloxy phenyl porphyrin (chemical combination
Thing 3) synthesis：
By 0.18 g of compound 2 and 2 grams of 1,6- hexamethylene diamines, under nitrogen protection, it is heated to 80 DEG C and stirs 24 hours.Reaction knot
Shu Hou, is cooled to room temperature, with water/methylene chloride volume ratio=1:2 extractions, anhydrous sodium sulfate drying organic layer, vacuum distillation is removed
Solvent.Purified with 200-300 mesh silica gel column chromatography（Leacheate is that dichloromethane/absolute methanol volume ratio is 10:1-5:1), obtain
To 0.16 gram of aubergine solid, yield is 83.2%.
(the own ester of 4) perylenes tetracarboxylic acid four（Compound 4）Synthesis：
3.5 Ke perylenetetracarboxylic dianhydrides are dissolved in during 400 milliliters of mass concentrations are 2.5% potassium hydroxide aqueous solution, are heated 70
DEG C stirring 1.5 hours, be cooled to suction filtration after room temperature, the pH of filtrate is adjusted to 9-10.By 14.72 grams of hexyl bromide 1 bromohexanes, 3.94 grams of first
Base trioctylmethylammonium chloride is added in filtrate, is heated to 100 DEG C and is stirred 6 hours.After being cooled to room temperature, 50 milliliters of dichloromethanes are added
Alkane is extracted, and uses anhydrous sodium sulfate drying organic layer, and vacuum distillation removes solvent.Crude product dichloromethane/absolute ethyl alcohol volume
Than=1:1 recrystallization suction filtration, filtration under diminished pressure obtains yellow powder（6.51 grams, yield 95%）.IR(KBr) νmax (cm-1):
3430, 2930 (C-H), 2850 (C-H), 1730 (C=O), 1630, 1460, 1400, 1270 (C-O), 1170,
1000, 747. 1H NMR (500 MHz, CDCl3) δ/ppm: 8.15 (d, J = 8.0 Hz, 2 H), 8.09 (d,
J = 8.0 Hz, 2 H), 7.98-7.93 (m, 4 H), 4.35 (t, J =7.0 Hz, 8 H), 1.86-1.80 (m,
8 H), 1.50-1.37 (m, 24 H), 0.93 (t, J =7.0 Hz, 12 H)。
(5) perylene list acid anhydride dioctyl phthalate dihexyls（Compound 5）Synthesis：
6.51 g of compound 4 are dissolved completely in 3.6 milliliters of toluene and 18.0 milliliters of normal heptane solvents, 1.54 grams are added
P-methyl benzenesulfonic acid, is heated to 95 DEG C and stirs 5 hours, suction filtration after frozen water cooling, and filter cake dichloromethane/absolute methanol volume ratio=
1:1 recrystallization, is repeated twice, and obtains red solid（3.88 grams, yield is 79%）.IR(KBr) Vmax (cm-1): 3430,
2920 (C-H), 2850 (C-H), 1730 (C=O), 1630, 1290 (C-O), 1150 , 1010, 857, 805,
737. MS (ESI): calcd for C36H34O7H+ 579.23; found 580.20。
(6) dodecyloxy phenyl porphyrin benzamide hexane imines Qiao Lian perylene dihexyls binary compound (compound 6)
Synthesis：
By 0.11 g of compound 3,0.06 g of compound 5 and 1 gram of imidazoles, 5 are stirred under nitrogen protection, at being heated to 140 DEG C small
When.Room temperature is cooled to, 20 milliliters of hot water stirs of addition suction filtration after 10 minutes obtains the crude product of kermesinus, with 200-300 mesh silicon
Plastic column chromatography is purified（Leacheate is that dichloromethane/ethyl acetate volume ratio is 15:1-5:1) red solid, is obtained（0.06 gram,
Yield is 40%）.IR(KBr) νmax (cm-1): 2921.5（C-H), 2852.9, 1710(C=O), 1641, 1469,
1358, 1294, 1166(C-O), 1067, 963, 800. 1H NMR (500 MHz, CDCl3) δ/ppm 8.89 (s,
3H), 8.80 (d, J = 4.5 Hz, 1H), 8.59 (d, J = 8.0 Hz, 1H), 8.39 (m, 2H), 8.31
(d, J = 8.0 Hz, 1H), 8.23 (d, J = 8.0 Hz, 1H), 8.15–8.03 (m, 4H), 7.26 (s,
2H), 6.76 (s, 1H), 5.45–5.30 (m, 1H), 4.34 (t, J = 7.0 Hz, 2H), 4.31–4.21 (m,
4H), 3.68 (m, 1H), 2.33–2.13 (m, 1H), 0.92 (m, 8H), -2.75 (s, 1H). MS (ESI):
calcd for C123H148N6O10 Na+ 1870.1; found 1893.3. Elemental analysis calcd for
C123H148N6O10: C, 78.98; H, 7.98; N, 4.49, found: C, 78.97, H, 8.23, N, 4.56。
Claims (1)
1. a kind of synthetic method of dodecyloxy phenyl porphyrin benzamide hexane imines Qiao Lian perylene dihexyl binary compounds,
It is characterized in that concretely comprising the following steps:
(1) be to dodecyloxy benzaldehyde compound 1 synthesis：
By 2.44 grams of parahydroxyben-zaldehydes, 6.73 grams of bromododecanes and 5.52 grams of Anhydrous potassium carbonates, 20 milliliters are dissolved in through CaH2It is dry
Dry N,N-dimethylformamide solvent；Under nitrogen protection, it is heated to 80 DEG C and stirs 12 hours；Room temperature is cooled to, by reaction solution
Pour into 100 milliliters of water, extracted with 20 milliliters of dichloromethane, organic layer, rotated evaporimeter are dried with anhydrous sodium sulfate
After removing solvent, purified with 200-300 mesh silica gel column chromatography, leacheate is dichloromethane：Petroleum ether volume ratio is 1:5-1:2,
Obtain weak yellow liquid i.e. 1,5.75 grams of compound, yield 98%；bp >300℃, IR(KBr) νmax (cm-1):1610,
1380,1260, 841; 1H NMR (300 MHz, CDCl3) δ/ppm: 9.87(s, H), 7.68(t, J = 6.9 Hz,
2H), 6.89 (d, J = 8.4 Hz,2 H), 3.99 (t, J = 6.9 Hz, 2 H), 1.83-1.76 (m, J =
6.9 Hz, 4 H), 0.96-1.31 (m, J = 5.4 Hz, 10 H)；
(2) 5- para Toluic Acids carbomethoxy -10,15,20- three is the synthesis of compound 2 to dodecyloxy phenyl porphyrin：
By 1,1.20 grams of 5.88 g of compound to acyl group methyl benzoate and 1.85 grams of m-Nitrobenzoic Acids, 32 milliliters of diformazans are dissolved in
Benzole soln, 32 milliliters are added dropwise containing 1.91 grams of xylene solutions of pyrroles 10 minutes by constant pressure funnel, and 140 DEG C of heating is stirred
Mix 3.5 hours；Reaction terminates, and is cooled to room temperature, and 180 milliliters of absolute methanol is poured into reaction solution, and suction filtration after standing is obtained
Purple material, is purified with 200-300 mesh silica gel column chromatography, and leacheate is that dichloromethane/petroleum ether volume ratio is 1:2-1:1, use
Dichloromethane/absolute methanol volume ratio=1:1 recrystallization, obtains violet solid i.e. 2,2.3 grams of compound, yield 32.7%；Mp
125.1-126.2℃, IR(KBr) νmax (cm-1): 1720,1350,1240, 803; 1H NMR (400 MHz,
CDCl3) δ/ppm 8.90 (d, J = 6.0 Hz, 6H), 8.76 (d, J = 4.7 Hz, 2H), 8.44 (d, J =
8.0 Hz, 2H), 8.30 (d, J = 8.0 Hz, 2H), 8.16 -8.05 (m, 6H), 7.29 (d, J = 8.4
Hz, 6H), 4.15 (d, J = 5.6 Hz, 6H), 4.11 (s, 3H), 1.93 (m, 3H), 1.77 -1.54 (m,
12H), 1.51-1.35 (m, 12H), 1.06 (m 9H), 1.00 (t, J = 6.8 Hz, 9H), -2.74 (s,
2H)；
(3) 5- paraphenylene terephthalamides (6- amino-hexyls) -10,15,20- three is compound 3 to dodecyloxy phenyl porphyrin
Synthesis：
By 0.18 g of compound 2 and 2 grams of 1,6- hexamethylene diamines, under nitrogen protection, it is heated to 80 DEG C and stirs 24 hours；Reaction knot
Shu Hou, is cooled to room temperature, with water/methylene chloride volume ratio=1:2 extractions, anhydrous sodium sulfate drying organic layer, vacuum distillation is removed
Solvent；Purified with 200-300 mesh silica gel column chromatography, leacheate is that dichloromethane/absolute methanol volume ratio is 10:1-5:1, obtain
0.16 gram of aubergine solid, yield is 83.2%；
(the own ester of 4) perylenes tetracarboxylic acid four is the synthesis of compound 4：
3.5 Ke perylenetetracarboxylic dianhydrides are dissolved in during 400 milliliters of mass concentrations are 2.5% potassium hydroxide aqueous solution, are heated 70
DEG C stirring 1.5 hours, be cooled to suction filtration after room temperature, the pH of filtrate is adjusted to 9-10；By 14.72 grams of hexyl bromide 1 bromohexanes, 3.94 grams of first
Base trioctylmethylammonium chloride is added in filtrate, is heated to 100 DEG C and is stirred 6 hours；After being cooled to room temperature, 50 milliliters of dichloromethanes are added
Alkane is extracted, and uses anhydrous sodium sulfate drying organic layer, and vacuum distillation removes solvent；Crude product dichloromethane/absolute ethyl alcohol volume
Than=1:1 recrystallization suction filtration, filtration under diminished pressure obtains 6.51 grams of yellow powder, yield 95%；IR(KBr) νmax (cm-1): 3430,
2930 (C-H), 2850 (C-H), 1730 (C=O), 1630, 1460, 1400, 1270 (C-O), 1170, 1000,
747. 1H NMR (500 MHz, CDCl3) δ/ppm: 8.15 (d, J = 8.0 Hz, 2 H), 8.09 (d, J =
8.0 Hz, 2 H), 7.98-7.93 (m, 4 H), 4.35 (t, J =7.0 Hz, 8 H), 1.86-1.80 (m, 8
H), 1.50-1.37 (m, 24 H), 0.93 (t, J =7.0 Hz, 12 H)；
(5) perylene list acid anhydride dioctyl phthalate dihexyls are the synthesis of compound 5：
6.51 g of compound 4 are dissolved completely in 3.6 milliliters of toluene and 18.0 milliliters of normal heptane solvents, 1.54 grams are added
P-methyl benzenesulfonic acid, is heated to 95 DEG C and stirs 5 hours, suction filtration after frozen water cooling, and filter cake dichloromethane/absolute methanol volume ratio=
1:1 recrystallization, is repeated twice, and obtains 3.88 grams of red solid, and yield is 79%；IR(KBr) Vmax (cm-1): 3430, 2920
(C-H), 2850 (C-H), 1730 (C=O), 1630, 1290 (C-O), 1150 , 1010, 857, 805, 737.
MS (ESI): calcd for C36H34O7H+579.23; found 580.20；
(6) dodecyloxy phenyl porphyrin benzamide hexane imines Qiao Lian perylene dihexyl binary compounds are the conjunction of compound 6
Into：
By 0.11 g of compound 3,0.06 g of compound 5 and 1 gram of imidazoles, 5 are stirred under nitrogen protection, at being heated to 140 DEG C small
When；Room temperature is cooled to, 20 milliliters of hot water stirs of addition suction filtration after 10 minutes obtains the crude product of kermesinus, with 200-300 mesh silicon
Plastic column chromatography is purified, and leacheate is that dichloromethane/ethyl acetate volume ratio is 15:1-5:1, red solid is obtained, 0.06 gram, produce
Rate is 40%；IR(KBr) νmax (cm-1): 2921.5（C-H), 2852.9, 1710(C=O), 1641, 1469, 1358,
1294, 1166(C-O), 1067, 963, 800. 1H NMR (500 MHz, CDCl3) δ/ppm 8.89 (s, 3H),
8.80 (d, J = 4.5 Hz, 1H), 8.59 (d, J = 8.0 Hz, 1H), 8.39 (m, 2H), 8.31 (d, J
= 8.0 Hz, 1H), 8.23 (d, J = 8.0 Hz, 1H), 8.15–8.03 (m, 4H), 7.26 (s, 2H),
6.76 (s, 1H), 5.45–5.30 (m, 1H), 4.34 (t, J = 7.0 Hz, 2H), 4.31–4.21 (m, 4H),
3.68 (m, 1H), 2.33–2.13 (m, 1H), 0.92 (m, 8H), -2.75 (s, 1H). MS (ESI): calcd
for C123H148N6O10 Na+ 1870.1; found 1893.3. Elemental analysis calcd for
C123H148N6O10: C, 78.98; H, 7.98; N, 4.49, found: C, 78.97, H, 8.23, N, 4.56；
It is pure that the chemical reagent and solvent for being used are analysis.
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