An axially chiral porphyrin compound with long chain ester structure and its preparation method and application

Abstract

The application relates to the technical field of organic chemical synthesis, and discloses an axially chiral porphyrin compound with a long-chain ester structure and a preparation method and application thereof. The compound has a structure shown in formula (I), formula (I), wherein R is n is 6, 8, 10, 12, 14 or 16. The method provided by the application has great significance for the study of an axially chiral long-chain compound family, and proves that the chain length of a raw material greatly influences the liquid crystal properties of an obtained axially chiral long-chain compound, and can inspire the synthesis of an axially chiral porphyrin compound with a longer chain.

Description

Technical Field

[0001] This invention relates to the field of organic chemical synthesis technology, specifically to an axially chiral porphyrin compound with a long-chain ester structure, its preparation method, and its application. Background Technology

[0002] Metalloporphyrin complexes and their derivatives in living organisms generally have proteins surrounding them, providing a favorable natural chiral environment. Inspired by this, chemical researchers have designed and modified porphyrin compounds containing chiral environments in biomimetic chemistry.

[0003] Liquid crystals are an ordered state between liquid and crystalline states, exhibiting the fluidity of liquids and the anisotropy of crystals. Liquid crystal compounds possess excellent intermolecular arrangement and can be used as semiconductor materials in photovoltaic devices. The substituents of porphyrin derivatives exhibiting liquid crystal properties are typically alkyl, alkoxy, acyl, ester, and alkylamide groups.

[0004] JW Goodby disclosed the first porphyrin liquid crystal molecule in "Mol. Cryst. Liq. Cryst. 1980, 56, 303–309." Researchers disclosed porphyrin derivatives exhibiting discoid liquid crystal characteristics in "J. Am. Chem. Soc. 1989, 111, 3024–3029." MAEDA et al. disclosed long-chain alkyl-substituted porphyrin liquid crystals in "Liquid Crystals. 1998, 25, 537-542." The discoid lamellar phase was bidirectional at lower pressures and unidirectional above 240 MPa and 170 °C.

[0005] In their paper "Synthesis and Property Study of Meso-5,10,15,20-Tetratetra[3,5-Di(Octayloxy)phenyl]porphyrin Metal Complexes," Sun Erjun et al. disclosed a method using 3,5-dimethoxybenzaldehyde and pyrrole as raw materials. A porphyrin ligand was prepared via a condensation reaction, and then reacted with octanoyl chloride to obtain an octane ester-substituted long-chain porphyrin. This porphyrin was then complexed with zinc metal, and the liquid crystal properties of the compound were determined. However, the long-chain porphyrins obtained by this method are not chiral, and only octanoyl chloride is used as a raw material; the influence of chain length on liquid crystal properties was not investigated. Summary of the Invention

[0006] The purpose of this invention is to provide an axially chiral porphyrin compound with a long-chain ester structure and a method for preparing the same.

[0007] To achieve the above objectives, a first aspect of the present invention provides an axially chiral porphyrin compound having a long-chain ester structure, the compound having the structure shown in formula (I).

[0008] Where R is n is 6, 8, 10, 12, 14 or 16.

[0009] A second aspect of the present invention provides a method for preparing the compound of formula (I) according to the first aspect of the present invention, the method comprising: adding the compound of formula (I-1), a long-chain acyl chloride compound, and a base reagent to an organic solvent under a protective atmosphere to carry out a one-pot reaction;

[0010] The compound represented by formula (I-1) has the following structure:

[0011]

[0012] The long-chain acyl chloride compound is C8H. 15 ClO, C 10 H 19 ClO, C 12 H 23 ClO, C 14 H 27 ClO, C 16 H 31 ClO, C 18 H 35 At least one of ClO;

[0013] The molar ratio of the compound shown in formula (I-1), the long-chain acyl chloride compound, and the base reagent is 1:5-15:3-8.

[0014] A third aspect of the present invention provides the application of the axially chiral porphyrin compounds described in the second aspect of the present invention in the field of axially chiral organic materials.

[0015] The method provided by this invention is of great significance for the study of axially chiral long-chain compound families, and it has been confirmed that the chain length of the raw materials has a significant impact on the liquid crystal properties of the obtained axially chiral long-chain compounds, which can inspire the synthesis of even longer-chain axially chiral porphyrin compounds. Attached Figure Description

[0016] Figure 1 This is a DSC test curve of the axially chiral porphyrin compound obtained in Example 1 of the present invention;

[0017] Figure 2 This is a DSC test curve of the axially chiral porphyrin compound obtained in Example 4 of the present invention;

[0018] Figure 3 This is a DSC test curve of the axially chiral porphyrin compound obtained in Example 5 of the present invention;

[0019] Figure 4 This is a DSC test curve of the axially chiral porphyrin compound obtained in Example 6 of the present invention. Detailed Implementation

[0020] The endpoints and any values ​​of the ranges disclosed herein are not limited to the precise ranges or values, and these ranges or values ​​should be understood to include values ​​close to these ranges or values. For numerical ranges, the endpoint values ​​of the various ranges, the endpoint values ​​of the various ranges and individual point values, and individual point values ​​can be combined with each other to obtain one or more new numerical ranges, which should be considered as specifically disclosed herein.

[0021] As previously described, a first aspect of the present invention provides an axially chiral porphyrin compound having a long-chain ester structure, the compound having the structure shown in formula (I).

[0022] Where R is n is 6, 8, 10, 12, 14 or 16.

[0023] As previously stated, a second aspect of the present invention provides a method for preparing the compound of formula (I) as described in the first aspect of the present invention, characterized in that the method comprises: adding the compound of formula (I-1), a long-chain acyl chloride compound, and a base reagent to an organic solvent under a protective atmosphere to carry out a one-pot reaction;

[0024] The compound represented by formula (I-1) has the following structure:

[0025]

[0026] The long-chain acyl chloride compound is C8H. 15 ClO, C 10 H 19 ClO, C 12 H 23 ClO, C 14 H 27 ClO, C 16 H 31 ClO, C 18 H 35 At least one of ClO;

[0027] The molar ratio of the compound shown in formula (I-1), the long-chain acyl chloride compound, and the base reagent is 1:5-15:3-8.

[0028] Preferably, the alkaline reagent is selected from at least one of potassium tert-butoxide, triethylamine, potassium hydroxide, and sodium hydroxide.

[0029] More preferably, the base reagent is triethylamine. The inventors of this invention have discovered that, under this preferred condition, the compound obtained by this invention has a higher yield.

[0030] Preferably, the molar ratio of the compound shown in formula (I-1), the long-chain acyl chloride compound, and the base reagent is 1:10:5. The inventors of this invention have discovered that, under this preferred condition, the compound obtained by this invention has a higher yield.

[0031] In a preferred embodiment, the one-pot reaction involves first adding the compound of formula (I-1) and the base reagent to the organic solvent, and then adding the long-chain acyl chloride compound.

[0032] Preferably, the one-pot reaction involves first adding the compound shown in formula (I-1) and the base reagent to the organic solvent and stirring, then heating to the reaction temperature required for the one-pot reaction, and then adding the long-chain acyl chloride compound dropwise; the stirring speed is 200-400 rpm.

[0033] Preferably, the organic solvent is selected from at least one of chloroform, dichloromethane, tetrahydrofuran, acetonitrile, and toluene.

[0034] Preferably, the amount of organic solvent used is 2-4 mL relative to 0.01 mmol of the compound represented by formula (I-1).

[0035] More preferably, the conditions for the one-pot reaction are at least: a temperature of 60-80°C and a time of 24-48 hours.

[0036] Preferably, the one-pot reaction is carried out under stirring, and the conditions for the one-pot reaction are at least satisfied: the rotation speed is 200-400 rpm.

[0037] Preferably, the conditions for the one-pot reaction are at least: a temperature of 70°C and a time of 36 hours.

[0038] In a preferred embodiment, the method further includes: after the one-pot reaction, the intermediate product is subjected to extraction, vacuum concentration, and purification separation in sequence.

[0039] The present invention does not have any special requirements for the extraction process, as long as the organic phase is obtained. For example, the extraction process is to extract with distilled water 2-3 times.

[0040] Preferably, the vacuum concentration process is carried out in a vacuum rotary evaporator, and the conditions for the vacuum concentration process are at least: a temperature of -5 to -3°C and a time of 3 to 8 minutes.

[0041] More preferably, the purification and separation process is carried out using a thin-layer chromatography column, and the developing solvent is petroleum ether: dichloromethane = 1:1.

[0042] Preferably, the protective atmosphere is argon.

[0043] In this invention, there are no particular limitations on the apparatus for the one-pot reaction. For example, the one-pot reaction is carried out in a Schlenk tube with a specification of 10 mL. The Schlenk tube is pretreated as follows: it is first cleaned with deionized water and then placed in an oven and dried at 120°C for 3 hours.

[0044] As previously stated, the third aspect of the present invention provides the application of the axially chiral porphyrin compounds described in the first aspect of the present invention in the field of axially chiral organic materials.

[0045] The present invention will be described in detail below through examples. In the following examples, unless otherwise specified, the raw materials are all commercially available products.

[0046] The Schlenk tubes used are 10 mL in size. The Schlenk tubes are pretreated as follows: they are first cleaned with deionized water and then placed in an oven to dry at 120°C for 3 hours.

[0047] Among them, the nuclear magnetic resonance spectrometers, namely the ARX-400 (400M) and ARX-600 (600M) models, were purchased from Bruker.

[0048] The synthesis method and steps of the compound shown in formula (I-1) are as disclosed in the prior art with application number 202311789484.8; as mentioned above, the structural formula of the compound shown in formula (I-1) is:

[0049] In the following examples, the compound represented by formula (I-1) is denoted as 1a.

[0050] Example 1

[0051] 12.38 mg of 1a (0.01 mmol) was placed in a Schlenk tube, sealed, and the air inside the tube was purged with argon three times. Then, triethylamine and chloroform solutions were added, and the mixture was stirred at 300 rpm and heated to 70°C. C8H was then added dropwise. 15 ClO was added, and the reaction was continued at 70°C for 36 hours to obtain the intermediate product.

[0052] Among them, 1a and C8H 15 The molar ratio of ClO and triethylamine is 1:10:5;

[0053] The volume of the chloroform solution used is 2 mL relative to 0.01 mmol of 1a;

[0054] The intermediate product was extracted three times with distilled water. The organic phase was placed in a vacuum rotary evaporator and distilled under reduced pressure at -3°C for 5 min. The product was then purified and separated by thin-layer chromatography (petroleum ether: dichloromethane = 1:1) to obtain an axially chiral long-chain porphyrin compound, denoted as Porphrin-a.

[0055] The obtained Porphrin-a had a mass of 19.3 mg, and the Porphrin-a had the following structural formula:

[0056]

[0057] Porphrin-a,Purple solid; 1H NMR (600MHz, CDCl3) δ9.73(s,4H),8.25(d,J=9.0Hz,4H),8.08(d,J=8.3Hz,4H),7.69(d,J=9.0Hz,4H),7.4 7(t,J=7.8Hz,4H),7.23(d,J=8.6Hz,4H),7.01(t,J=8.0Hz,4H),6.87(d,J=7.2Hz,8H),6.73(t,J=7.4Hz,4 H),6.66(t,J=7.6Hz,8H),4.88(d,J=15.3Hz,4H),4.79(d,J=15.3Hz,4H),1.75–1.69(m,4H),1.67–1.62(m ,4H),1.07–1.00(m,8H),0.69–0.62(m,16H),0.61–0.46(m,16H),0.40(t,J=7.3Hz,12H),-3.16(s,2H).13C NMR (101MHz, CDCl3) δ172.1,148.3,141.1,135.4,131.9,130.2,129.0,128.1,127.9,127.1 ,126.6,125.7,125.4,124.1,122.2,101.6,33.8,33.3,31.2,28.6,28.5,24.4,22.2,13.7.

[0058] Example 2

[0059] 12.38 mg of 1a (0.01 mmol) was placed in a Schlenk tube, sealed, and the air inside the tube was purged with argon three times. Then, triethylamine and chloroform solutions were added, and the mixture was stirred at 200 rpm and heated to 75°C. C was then added dropwise. 10 H 19 ClO was added, and the reaction was continued at 75°C for 24 hours to obtain the intermediate product.

[0060] Among them, 1a and C 10 H 19 The molar ratio of ClO and triethylamine is 1:8:3;

[0061] The volume of the chloroform solution used is 3 mL relative to 0.01 mmol of 1a.

[0062] The intermediate product was extracted three times with distilled water. The organic phase was placed in a vacuum rotary evaporator and distilled under reduced pressure at -3°C for 5 min. The product was then purified and separated by thin-layer chromatography (petroleum ether: dichloromethane = 1:1) to obtain an axially chiral long-chain porphyrin compound, denoted as Porphrin-b.

[0063] The obtained Porphrin-b mass is 20 mg, and the Porphrin-b has the following structural formula:

[0064]

[0065] Porphrin-b,red solid; 1H NMR (400MHz, CDCl3) δ9.75 (s, 4H), 8.26 (d, J = 9.0Hz, 4H), 8.09 (d, J = 8.3Hz, 4H), 7.70 (d, J = 8.9Hz, 4 H),7.47(t,J=7.4Hz,4H),7.23(d,J=8.5Hz,4H),7.01(t,J=7.5Hz,4H),6.88(d,J=6.4Hz,8H),6.76– 6.70(m,4H),6.67(t,J=7.6Hz,8H),4.90(d,J=15.1Hz,4H),4.80(d,J=15.8Hz,4H),1.79–1.71(m,4H ),1.69–1.63(m,4H),1.15–1.05(m,16H),0.98–0.89(m,16H),0.83–0.72(m,36H),-3.14(s,2H).13C NMR (101MHz, CDCl3) δ172.1,148.3,141.1,135.5,131.9,130.2,129.0,128.1,127.9,127.2,126.6 2,125.7,125.4,124.1,122.2,101.7,33.8,33.3,31.7,29.2,29.1,29.0,28.8,24.50,22.6,14.1.

[0066] Example 3

[0067] 12.38 mg of 1a (0.01 mmol) was placed in a Schlenk tube, sealed, and the air inside the tube was purged with argon three times. Then, triethylamine and chloroform solutions were added, and the mixture was stirred at 200 rpm and heated to 65°C. C was then added dropwise. 12 H 23 ClO was added, and the reaction was continued at 65°C for 40 hours to obtain the intermediate product.

[0068] Among them, 1a and C 12 H 23 The molar ratio of ClO and triethylamine is 1:15:8;

[0069] The volume of the chloroform solution used is 2 mL relative to 0.01 mmol of 1a;

[0070] The intermediate product was extracted three times with distilled water. The organic phase was placed in a vacuum rotary evaporator and distilled under reduced pressure at -3°C for 5 min. The product was then purified and separated by thin-layer chromatography (petroleum ether: dichloromethane = 1:1) to obtain an axially chiral long-chain porphyrin compound, denoted as Porphrin-c.

[0071] The obtained Porphrin-c had a mass of 18.7 mg, and the Porphrin-c had the following structural formula:

[0072]

[0073] Porphrin-c,red solid;1H NMR (400MHz, CDCl3) δ9.73(s,4H),8.25(d,J=9.0Hz,4H),8.08(d,J=8.2Hz,4H),7.68(d,J=8.9Hz,4H),7.47(t, J=7.4Hz,4H),7.24(d,J=8.5Hz,4H),7.01(t,J=7.6Hz,4H),6.87(d,J=7.0Hz,8H),6.72(t,J=7.2Hz,4H),6.65(t ,J=7.4Hz,8H),4.89(d,J=15.2Hz,4H),4.78(d,J=15.2Hz,4H),1.77–1.69(m,4H),1.66–1.60(m,4H),1.22(t,J= 7.1Hz,8H),1.16–1.07(m,24H),1.05–0.99(m,8H),0.94–0.90(m,8H),0.84(t,J=7.1Hz,36H),-3.16(s,2H).13C NMR (101MHz, CDCl3) δ172.1,148.3,141.1,135.5,131.9,130.2,129.0,128.1,127.9,127.2,126.6,125 .7,125.4,124.2,122.2,101.6,33.8,33.3,32.0,29.6,29.5,29.4,29.3,29.1,28.8,24.5,22.8,14.2.

[0074] Example 4

[0075] This example follows the method in Example 1, except that C is used. 14 H 27 ClO replaces the C8H 15 ClO, and the remaining steps and parameters are the same as in Example 1. An axially chiral long-chain porphyrin compound, denoted as Porphrin-d, is obtained.

[0076] The obtained Porphrin-d had a mass of 18 mg, and the Porphrin-d had the following structural formula:

[0077]

[0078] Porphrin-d, red solid; 1H NMR (400MHz, CDCl3) δ9.72 (s, 4H), 8.25 (d, J = 8.9Hz, 4H), 8.08 (d, J = 8.2Hz, 4H) ,7.68(d,J=8.8Hz,4H),7.47(t,J=7.4Hz,4H),7.23(d,J=8.6Hz,4H),7.01(t,J =7.6Hz,4H),6.86(d,J=7.3Hz,8H),6.72(t,J=7.1Hz,4H),6.64(t,J=7.4Hz,8H ),4.88(d,J=15.1Hz,4H),4.78(d,J=15.1Hz,4H),1.75–1.67(m,4H),1.65–1.58 (m,4H),1.20(s,24H),1.09(s,16H),1.01(t,J=5.6Hz,8H),0.96–0.71(m,52H) ,-3.18(s,2H).13CNMR(151MHz,CDCl3)δ172.2,148.2,141.1,135.4,131.9,130 .2,129.0,128.1,127.9,127.1,126.6,125.7,125.4,124.1,122.2,101.6,33.8,33.3,32.1,29.8,29.7,29.5,29.5,29.5,29.3,29.1,28.8,24.5,22.8,14.3.

[0079] Example 5

[0080] This example follows the method in Example 1, except that C is used. 16 H 31 ClO replaces the C8H 15 ClO, and the remaining steps and parameters are the same as in Example 1. An axially chiral long-chain porphyrin compound, denoted as Porphrin-e, is obtained.

[0081] The obtained Porphrin-e had a mass of 23.1 mg, and the Porphrin-e had the following structural formula:

[0082]

[0083] Porphrin-e, red solid; 1H NMR (400MHz, CDCl3) δ9.76 (s, 4H), 8.28 (d, J = 9.0Hz, 4H), 8.11 (d, J = 8.3Hz, 4H), 7.72(d,J=9.0Hz,4H),7.50(t,J=7.4Hz,4H),7.28(s,4H),7.04(t,J=7.7Hz,4H) ,6.90(d,J=7.3Hz,8H),6.74(d,J=7.2Hz,4H),6.68(t,J=7.4Hz,8H),4.92(d,J= 15.2Hz,4H),4.82(d,J=15.2Hz,4H),1.80–1.71(m,4H),1.69–1.61(m,4H),1.29– 1.21(m,40H),1.13(s,16H),1.05(t,J=7.4Hz,8H),1.00–0.77(m,52H),-3.13(s ,2H).13CNMR(101MHz,CDCl3)δ172.1,148.3,141.1,135.5,131.9,130.2,129.0 ,128.1,127.9,127.2,126.6,125.7,125.4,124.2,122.2,101.7,33.8,33.3,32.1,29.9,29.9,29.8,29.8,29.7,29.6,29.5,29.3,29.1,28.8,24.5,22.8,14.2.

[0084] Example 6

[0085] This example follows the method in Example 1, except that C is used. 18 H 35 ClO replaces the C8H 15 ClO, the remaining steps and parameters are the same as in Example 1. An axially chiral long-chain porphyrin compound, denoted as Porphrin-f, is obtained.

[0086] The obtained Porphrin-f had a mass of 21.1 mg, and the Porphrin-f had the following structural formula:

[0087]

[0088] Porphrin-f,red solid;1H NMR (600MHz, CDCl3) δ9.63 (s, 4H), 8.14 (d, J = 9.0Hz, 4H), 7.96 (d, J = 8.4Hz, 4H), 7.58 (d, J = 8.9Hz, 4H), 7.35(t,J=7.6Hz,4H),7.16–7.10(m,4H),6.90(t,J=7.8Hz,4H),6.76(d,J=7.7Hz,8H),6.61(t,J=7.2Hz ,4H),6.54(t,J=7.4Hz,8H),4.78(d,J=15.6Hz,4H),4.68(d,J=15.5Hz,4H),1.65–1.58(m,4H),1.54–1 .48(m,4H),1.15–1.03(m,48H),0.99(s,16H),0.94–0.88(m,8H),0.87–0.55(m,60H),-3.27(s,1H).13C NMR (151MHz, CDCl3) δ172.0,148.1,140.9,135.3,131.8 130.0,128.9,127.9,127.7,127.0,126.5,125.6,125.2,124.0,122.0,101.5,33.6,33.1,31 .9,29.7,29.7,29.7,29.7,29.6,29.5,29.4,29.4,29.4,29.2,28.9,28.6,24.3,22.7,14.1.

[0089] Comparative Example 1

[0090] This example follows the method described in Example 1, except that the molar ratio of the compound shown in formula (I-1), the long-chain acyl chloride compound, and the base reagent is 1:16:5. The remaining steps and parameters are the same as in Example 1. An axially chiral long-chain porphyrin compound, denoted as Porphrin-a-D1, is obtained.

[0091] Comparative Example 2

[0092] This example follows the method described in Example 1, except that the molar ratio of the compound shown in formula (I-1), the long-chain acyl chloride compound, and the base reagent is 1:10:9. The remaining steps and parameters are the same as in Example 1. An axially chiral long-chain porphyrin compound, denoted as Porphrin-a-D2, is obtained.

[0093] The yields of the axially chiral porphyrin compounds prepared in the above examples and comparative examples were calculated, and the results are shown in Table 1.

[0094] Table 1

[0095] Example 1 52 Example 2 51 Example 3 45 Example 4 41 Example 5 50 Example 6 44 Comparative Example 1 40 Comparative Example 2 39

[0096] As can be seen from the results in Table 1, the axially chiral porphyrin compounds obtained by using the embodiments of the present invention have significantly higher yields.

[0097] Test case

[0098] DSC tests were performed on the axially chiral porphyrin compounds prepared in the above embodiments and comparative examples. Exemplarily, Figure 1 The DSC test curve of the axial chiral porphyrin compound obtained in Example 1 of the present invention is shown. Figure 2 The DSC test curve of the axially chiral porphyrin compound obtained in Example 4 of the present invention is shown. Figure 3 The DSC test curve of the axially chiral porphyrin compound obtained in Example 5 of the present invention is shown. Figure 4 The DSC test curve of the axially chiral porphyrin compound obtained in Example 6 of the present invention is shown.

[0099] Depend on Figures 1-4 It can be seen that C8H is used 15 ClO, C 14 H 27 ClO, C 16 H 31 ClO, the axially chiral porphyrin compound obtained from the reaction raw materials, showed no phase transition range in either the heating or cooling curves during DSC testing, therefore it does not possess liquid crystal properties. Using C... 18 H 35 ClO is an axially chiral porphyrin compound obtained from the reaction raw materials. In DSC testing, both the heating and cooling curves show a phase transition range, thus exhibiting liquid crystal properties, and is a heating-cooling interconvertible liquid crystal.

[0100] The preferred embodiments of the present invention have been described in detail above; however, the present invention is not limited thereto. Within the scope of the inventive concept, various simple modifications can be made to the technical solutions of the present invention, including combinations of various technical features in any other suitable manner. These simple modifications and combinations should also be considered as the content disclosed in the present invention and are all within the protection scope of the present invention.

Claims

1. A chiral porphyrin compound having a long-chain ester structure, characterized in that, The compound has the structure shown in formula (I). Equation (I), where R is n is 16.

2. A method for preparing the axially chiral porphyrin compound having a long-chain ester structure as described in claim 1, characterized in that, The method includes: under a protective atmosphere, adding the compound shown in formula (I-1), the long-chain acyl chloride compound, and the base reagent to an organic solvent to carry out a one-pot reaction; The compound represented by formula (I-1) has the following structure: Equation (I-1); The long-chain acyl chloride compound is C. 18 H 35 ClO; The molar ratio of the compound shown in formula (I-1), the long-chain acyl chloride compound, and the base reagent is 1:5-15:3-8.

3. The method according to claim 2, wherein, The alkaline reagent is selected from at least one of potassium tert-butoxide, triethylamine, potassium hydroxide, and sodium hydroxide.

4. The method according to claim 2 or 3, wherein, The molar ratio of the compound shown in formula (I-1), the long-chain acyl chloride compound, and the base reagent is 1:10:

5.

5. The method according to claim 4, wherein, The one-pot reaction involves first adding the compound shown in formula (I-1) and the base reagent to the organic solvent, and then adding the long-chain acyl chloride compound.

6. The method according to claim 5, wherein, The organic solvent is selected from at least one of chloroform, dichloromethane, tetrahydrofuran, acetonitrile, and toluene; And / or, relative to 0.01 mmol of the compound shown in formula (I-1), the amount of the organic solvent used is 2-4 mL.

7. The method according to claim 6, wherein, The conditions for the one-pot reaction must at least meet the following requirements: temperature 60-80℃ and time 24-48h.

8. The method according to claim 7, wherein, The method further includes: after the one-pot reaction, the final product is subjected to extraction, vacuum concentration, and purification separation in sequence.

9. The method according to claim 8, wherein, The protective atmosphere is argon.

10. The application of the axially chiral porphyrin compound of claim 1 in the field of axially chiral organic liquid crystal materials.

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