CN113943300A - Preparation method and application of 2, 7-dimethoxycarbazole fused compound - Google Patents

Preparation method and application of 2, 7-dimethoxycarbazole fused compound Download PDF

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CN113943300A
CN113943300A CN202010678050.0A CN202010678050A CN113943300A CN 113943300 A CN113943300 A CN 113943300A CN 202010678050 A CN202010678050 A CN 202010678050A CN 113943300 A CN113943300 A CN 113943300A
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杨鹏
汤浩东
吴思
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Shenyang Pharmaceutical University
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Abstract

The invention relates to a 2, 7-dimethoxycarbazole fused compound, a preparation method and application thereof, in particular to a synthetic method of the compound and application thereof as a fluorescent molecular probe, belonging to the technical fields of chemical environment sensing and biology. The invention provides a series of 2, 7-dimethoxycarbazole fused compounds or salts thereof, wherein the chemical structure general formula is as follows: wherein, R, R1‑R7As described in the claims and specification. The compound can be used as a chemical sensor sensitive to solvent environment and temperature, and can also be prepared into a fluorescent probe molecule for identifying specific DNA.

Description

Preparation method and application of 2, 7-dimethoxycarbazole fused compound
Technical Field
The invention relates to a 2, 7-dimethoxycarbazole fused compound, a preparation method and application thereof, in particular to a synthetic method of the compound and application thereof as a fluorescent molecular probe, belonging to the technical fields of chemical environment sensing and biology.
Background
Vibration induced luminescence (VIE) is a new class of luminescence mechanisms that are highly sensitive to changes in the microenvironment. When molecules with the light-emitting mechanism are stimulated by external environment (temperature, solution viscosity, polarity and humidity), the spatial conformation of the molecules can be changed, fluorescence with different wavelengths is emitted, and the fluorescent sensing performance is excellent. At present, fluorescent probe molecules of VIE type luminescence mechanism are very rare.
Disclosure of Invention
The invention provides a series of 2, 7-dimethoxycarbazole fused compounds or salts thereof, wherein the chemical structure general formula is as follows:
Figure BDA0002584697960000011
r is hydrogen, 6-10-membered aryl, 5-10-membered heterocyclic group, 5-10-membered heteroaryl, C1-C10 alkyl and C1-C10 alkoxy, the heterocyclic group or the heteroaryl contains 1-3 heteroatoms of N, O or S, and the R can be substituted by one or more substituents of C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkoxy substituted by C1-C4 alkyl and C1-C4 acyl.
R1Is hydrogen, halogen, hydroxyl, C1-C4 aldehyde group, carboxyl, C1-C6 ester group, C1-C10 alkyl, C1-C10 alkoxy.
R2Is hydrogen, halogen, hydroxyl, C1-C4 aldehyde group, carboxyl, C1-C6 ester group, C1-C10 alkyl, C1-C10 alkoxy.
R3Is hydrogen, halogen, hydroxyl, C1-C4 aldehyde group, carboxyl, C1-C6 ester group, C1-C10 alkyl, C1-C10 alkoxy.
R4、R5Hydrogen, halogen, cyano, C1-C6 ester group, carboxyl, C1-C4 aldehyde group, nitro and sulfonic group.
R6、R7Is hydrogen, C1-C10 alkyl, C1-C10 alkoxy, 6-10 membered aryl, 5-10 membered heterocyclyl, 5-10 membered heteroaryl, R6、R7May be substituted by one or more substituents selected from the group consisting of C1-C4 alkyl, C1-C4 ester substituted by C1-C4 alkyl, C1-C4 alkoxy substituted by C1-C4 alkyl, and C1-C4 acyl, wherein the heterocyclic or heteroaryl group contains 1-3 heteroatoms selected from N, O and S.
The invention preferably relates to a novel 2, 7-dimethoxycarbazole condensed compound or a salt thereof with the following structural formula:
r is hydrogen, phenyl, 5-6 membered heterocyclic group, 5-6 membered heteroaryl, C1-C6 alkyl, C1-C6 alkoxy, the heterocyclic group or heteroaryl contains 1-3 heteroatoms N, O or S, the R can be substituted by one or more substituents, and the substituents are C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkyl substituted C1-C4 alkoxy, C1-C4 acyl.
R1Is hydrogen, halogen, hydroxyl, C1-C4 aldehyde group, carboxyl, C1-C6 ester group, C1-C6 alkyl, C1-C6 alkoxy.
R2Is hydrogen, halogen, hydroxyl, C1-C4 aldehyde group, carboxyl, C1-C6 ester group, C1-C6 alkyl, C1-C6 alkoxy.
R3Is hydrogen, halogen, hydroxyl, C1-C4 aldehyde group, carboxyl, C1-C6 ester group, C1-C6 alkyl, C1-C6 alkoxy.
R4、R5Hydrogen, halogen, cyano, carboxyl.
R6、R7Is hydrogen, C1-C6 alkyl, C1-C6 alkoxy, phenyl, 5-6 member heterocyclic radical, 5-6 member heteroaryl, R6、R7May be substituted by one or more substituents selected from the group consisting of C1-C4 alkyl, C1-C4 ester substituted by C1-C4 alkyl, C1-C4 alkoxy substituted by C1-C4 alkyl, and C1-C4 acyl, wherein the heterocyclic or heteroaryl group contains 1-3 heteroatoms selected from N, O and S.
The invention preferably relates to a novel 2, 7-dimethoxycarbazole condensed compound or a salt thereof with the following structural formula:
r is hydrogen, phenyl,
Figure BDA0002584697960000021
C1-C6 alkyl, C1-C6 alkoxy, wherein R can be substituted by one or more substituents, such as C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkyl-substituted C1-C4 alkoxy and C1-C4 acyl.
R1Hydrogen, C1-C6 alkyl, C1-C6 alkoxy.
R2Hydrogen, C1-C4 aldehyde group, C1-C6 alkyl group, C1-C6 alkoxy group.
R3Hydrogen, halogen, C1-C6 alkyl, C1-C6 alkoxy.
R4、R5Hydrogen, halogen, cyano, carboxyl.
R6、R7Is hydrogen, phenyl,
Figure BDA0002584697960000031
C1-C6 alkyl, C1-C6 alkoxy, said R6、R7Can be substituted by one or more substituents, such as C1-C4 alkyl, C1-C4 ester substituted by C1-C4 alkyl, C1-C4 alkoxy substituted by C1-C4 alkyl, and C1-C4 acyl.
The invention preferably relates to a novel 2, 7-dimethoxycarbazole condensed compound or a salt thereof with the following structural formula:
r is hydrogen, phenyl,
Figure BDA0002584697960000032
C1-C6 alkyl, (CH)2)2O(CH2)2OCH3。
R1Is hydrogen, C1-C6 alkoxy.
R2Hydrogen, a C1-C4 aldehyde group.
R3Is hydrogen or halogen.
R4、R5Hydrogen, halogen, cyano, carboxyl.
R6、R7Is hydrogen, phenyl,
Figure BDA0002584697960000033
(CH2)2O(CH2)2OCH3。
The invention preferably relates to a novel 2, 7-dimethoxycarbazole condensed compound with the following structural general formula:
Figure BDA0002584697960000034
Figure BDA0002584697960000041
The preparation method of the novel 2, 7-dimethoxycarbazole condensed compound comprises the following steps:
(1) preparation of compound a in the synthetic route:
taking 2, 7-dimethoxycarbazole powder and a 60% sodium hydride kerosene mixture, stirring for 0.5-2h at 50-60 ℃ in anhydrous tetrahydrofuran, then adding 1-bromo-2- (2-methoxyethoxy) ethane and the like, and reacting for 3-5h at room temperature to obtain a compound A.
(2) Preparation of compound B in the synthetic route:
and (3) adding the compound A and iodosuccinimide into a mixed solution of dichloromethane and glacial acetic acid, and stirring for 2-4h at room temperature in a dark place to obtain a compound B.
(3) Preparation of Compound C in the synthetic route
And adding the compound B, 2-nitrobenzeneboronic acid ester, cesium carbonate and palladium tetratriphenylphosphine into a mixed solvent of tetrahydrofuran and water, and refluxing for 8-10h to obtain a compound C.
(4) Preparation of Compound D in the synthetic route
And (3) dissolving the compound C and triphenylphosphine powder in an o-dichlorobenzene solution, and reacting at 180 ℃ for 10-12h to obtain a compound D.
The synthetic route is as follows:
Figure BDA0002584697960000051
wherein, R, R1、R3、R6、R7As set forth in claim, X is a bromine atom.
The compound can be used as a chemical sensor sensitive to solvent environment and temperature, and can also be prepared into a fluorescent probe molecule for identifying specific DNA.
Taking compound 1 as an example:
the compound 1 is VIE type fluorescent molecule with a novel structure, the fluorescence emission wavelength is between 520nm and 560nm, and the reverse lyotropic discoloration effect is realized, namely, the fluorescence wavelength is blue-shifted along with the increase of the polarity of a solvent. In addition, the molecules simultaneously have a thermochromic effect, and the long-wavelength fluorescence intensity is enhanced along with the increase of the temperature of the solution. Is a chemical sensor sensitive to solvent environment and temperature.
The compound 1 has a large aromatic ring conjugated system, is rich in pi electrons, can generate certain interaction with double-chain ds16 DNA, and can be developed into a fluorescent probe molecule for identifying specific DNA.
Drawings
FIG. 1 is a graph showing fluorescence spectra of Compound 1 (20. mu. mol/L) in different polar solvents;
FIG. 2 is a graph showing fluorescence spectra of Compound 1 (20. mu. mol/L) in different polar solvents;
FIG. 3 is a graph showing fluorescence spectra of Compound 1 (20. mu. mol/L) at various temperatures;
FIG. 4 is a schematic single crystal structure of Compound 1;
FIG. 5 is a fluorescence titration map of Compound 1 with ds 16.
Detailed Description
Example 1
Synthesis of compound a (compound 1 intermediate):
Figure BDA0002584697960000061
taking 2, 7-dimethoxycarbazole powder and a 60% sodium hydride kerosene mixture, stirring for 0.5h at 50 ℃ in anhydrous tetrahydrofuran, then adding 1-bromo-2- (2-methoxyethoxy) ethane, and reacting for 3h at room temperature to obtain a compound A. As a brown oily liquid, yield was 87%.
1H NMR(600MHz,DMSO-d6)δ7.86(d,J＝8.5Hz,2H),7.10(d,J＝2.3Hz,2H),6.75(dd,J＝8.4,2.2Hz,2H),4.47(t,J＝5.5Hz,2H),3.85(s,6H),3.77(t,J＝5.5Hz,2H),3.49(dd,J＝5.7,3.7Hz,2H),3.34(dd,J＝5.7,3.8Hz,2H),3.14(s,3H)；13C NMR(151MHz,DMSO)δ158.69,142.70,120.82,117.05,108.34,94.86,72.31,70.74,69.86,59.03,56.35,43.51,40.78,40.64,40.50；HRMS(ESI):m/z:[M+H]+calc:330.1700；found:330.1711
Example 2
Synthesis of compound B (compound 1 intermediate):
Figure BDA0002584697960000071
and (3) adding the compound A and iodosuccinimide into a mixed solution of dichloromethane and glacial acetic acid, and stirring for 2 hours at room temperature in a dark place to obtain a compound B which is a dark brown solid powder with the yield of 92%.
1H NMR(600MHz,DMSO-d6)δ8.46(s,2H),7.22(s,2H),4.53(t,J＝5.3Hz,2H),3.93(s,6H),3.78(t,J＝5.3Hz,2H),3.50–3.45(m,2H),3.32(t,J＝4.7Hz,3H),3.12(s,3H)；13C NMR(151MHz,DMSO)δ156.30,142.73,130.45,117.98,94.37,76.78,70.73,70.04,58.97,57.57,43.69,40.50；HRMS(ESI):m/z:[M+H]+calc:603.9458,found:603.9455.
Example 3
Synthesis of compound C (compound 1 intermediate):
Figure BDA0002584697960000072
and adding the compound B, 2-nitrobenzeneboronic acid ester, cesium carbonate and palladium tetratriphenylphosphine into a mixed solution of tetrahydrofuran and water, and reacting at 67 ℃ for 8-10h to obtain a compound C with the yield of 65%.
1H NMR(600MHz,DMSO-d6)δ8.06(s,2H),7.99–7.93(m,2H),7.78(td,J＝7.6,1.3Hz,2H),7.58(t,J＝7.2Hz,4H),7.25(s,2H),4.62(t,J＝5.3Hz,2H),3.84(t,J＝5.3Hz,2H),3.74(s,6H),3.54(t,J＝4.6Hz,2H),3.37(t,J＝4.7Hz,2H),3.16(s,3H)；13C NMR(151MHz,DMSO)δ154.47,149.91,142.09,133.62,133.47,133.29,128.33,124.07,121.08,119.48,116.54,93.13,71.76,70.17,69.59,58.46,55.72,43.18.
Example 4
Synthesis of compound D (compound 1 intermediate):
Figure BDA0002584697960000081
taking the compound C, triphenylphosphine powder and a small amount of o-dichlorobenzene solution, and reacting at 180 ℃ for 10h to obtain a compound D which is off-white solid powder with the yield of 53%.
1H NMR(600MHz,DMSO-d6)δ11.33(s,2H),8.24(d,J＝7.7Hz,2H),7.77(d,J＝8.0Hz,2H),7.37(t,J＝7.5Hz,2H),7.22(t,J＝7.5Hz,2H),7.10(s,2H),4.75(t,J＝5.7Hz,2H),4.17(s,6H),3.91(t,J＝5.6Hz,2H),3.55(t,J＝4.6Hz,2H),3.38(t,J＝4.7Hz,2H),3.17(s,3H)；13C NMR(151MHz,DMSO)δ154.58,140.90,139.72,134.43,124.17,123.90,122.09,120.22,111.86,107.19,100.89,85.79,72.39,70.82,70.04,59.06,56.59,44.31,40.50；HRMS(ESI):m/z:[M]+calc:507.2158，found:507.2153.
Example 5
Synthesis of target compound 1:
Figure BDA0002584697960000091
dissolving the compound D, 4, 5-difluorophthalonitrile and cesium carbonate in an N, N-dimethylformamide solution, and stirring at 80 ℃ for 3 hours to obtain a compound 1 which is orange red solid powder with the yield of 75%.
1H NMR(600MHz,DMSO-d6)δ8.26–8.22(m,2H),8.02(s,2H),7.76(d,J＝8.0Hz,2H),7.48(td,J＝7.6,1.4Hz,2H),7.44(td,J＝7.4,1.1Hz,2H),7.26(s,2H),4.70(t,J＝5.3Hz,2H),4.17(s,6H),3.89(t,J＝5.3Hz,2H),3.53(dd,J＝5.6,3.9Hz,2H),3.39–3.35(m,2H),3.16(s,3H).HRMS(ESI):m/z:[M+H]+calc:631.2220，found:631.2208.
Example 6
Synthesis of target compound 2:
Figure BDA0002584697960000092
taking the compound 1, phosphorus oxychloride, N, N-dimethylformamide and dichloromethane, and stirring for 10 hours at the temperature of minus 20 ℃. Compound 2 was obtained as an orange solid powder in 43% yield.
1H NMR(600MHz,DMSO-d6)δ10.59(s,1H),8.26(d,J＝7.7Hz,1H),8.20(d,J＝7.7Hz,1H),8.11(d,J＝8.9Hz,2H),7.80(dd,J＝11.2,8.1Hz,2H),7.58(t,J＝7.6Hz,1H),7.52(q,J＝7.5Hz,2H),7.45(t,J＝7.5Hz,1H),7.35(s,1H),4.83(ddt,J＝53.2,15.6,5.3Hz,2H),4.22(s,3H),4.18(s,3H),3.81(t,J＝5.3Hz,2H),3.45–3.34(m,2H),3.07(s,3H).13C NMR(151MHz,DMSO)δ189.02,159.65,155.36,144.50,144.06,142.95,142.07,141.81,140.77,138.53,137.21,136.91,136.07,127.62,126.56,126.12,125.39,124.63,123.91,122.43,122.27,115.56,115.16,115.08,113.51,113.05,112.84,111.84,109.74,107.26,101.86,89.83,71.64,70.06,69.91,64.73,58.28,56.54,47.20.HRMS(ESI):m/z:[M+Na]+calc:660.2247，found:660.2251.
Example 7
Synthesis of target compound 3:
Figure BDA0002584697960000101
taking the compound B, 2-nitro-4-methoxybenzeneboronic acid ester, cesium carbonate and palladium tetratriphenylphosphine, adding tetrahydrofuran and water as reaction solvents, reacting for 8-10h at 67 ℃ under the protection of nitrogen in a reaction system, and then carrying out the reaction steps of examples 4-5 to obtain a compound 3. Is orange red solid powder.
1H NMR(600MHz,DMSO-d6)δ8.07(s,1H),8.06(s,1H),7.32(d,J＝2.3Hz,1H),7.19(s,1H),7.04(dd,J＝8.6,2.3Hz,1H),4.64(t,J＝5.4Hz,1H),4.13(s,3H),3.87(s,3H),3.85(s,1H),3.52(t,J＝4.7Hz,1H),3.35(t,J＝4.8Hz,1H),3.15(s,2H).13C NMR(151MHz,DMSO)δ157.84,153.77,144.63,142.71,141.27,137.69,136.36,122.66,121.78,115.21,112.95,111.79,108.36,102.39,100.33,88.67,71.75,70.17,69.71,58.44,56.44,56.06,43.90.HRMS(ESI):m/z:[M+Na]+calc:692.2509，found:692.2509.
Example 8
Synthesis of target compound 4:
Figure BDA0002584697960000111
dissolving the compound 1 and potassium hydroxide in a mixed solution of water and ethanol, and heating and refluxing for 10 hours to obtain a compound 4 which is a pale yellow solid powder with the yield of 56%.
1H NMR(600MHz,DMSO-d6)δ8.24(d,J＝7.6Hz,1H),7.72(d,J＝8.0Hz,1H),7.68–7.59(m,1H),7.46(t,J＝7.6Hz,1H),7.40(t,J＝7.4Hz,1H),7.22(s,1H),4.68(t,J＝5.5Hz,1H),4.16(s,3H),3.89(t,J＝5.4Hz,1H),3.52(dd,J＝5.9,3.6Hz,1H),3.36(dd,J＝5.6,3.7Hz,1H),3.14(s,2H).13C NMR(151MHz,DMSO)δ167.01,154.33,143.51,142.00,139.44,138.59,131.89,127.89,124.70,123.14,122.11,115.15,107.97,102.44,88.40,71.74,70.19,69.72,58.41,56.45,43.96.HRMS(ESI):m/z:[M-H]-calc:668.2038，found:668.2079.
Example 9
Synthesis of target compound 5:
Figure BDA0002584697960000112
taking the compound D, 2,3,4,5, 6-pentafluorobenzonitrile and cesium carbonate, dissolving in a N, N-dimethylformamide solution, and stirring at 80 ℃ for 3h to obtain the compound 5 as a grey solid powder with the yield of 23%.
1H NMR(600MHz,DMSO-d6)δ8.30–8.12(m,2H),7.72(dd,J＝25.6,8.1Hz,2H),7.44(t,J＝7.6Hz,2H),7.38(q,J＝7.4Hz,2H),7.24(d,J＝14.2Hz,2H),4.67(t,J＝5.4Hz,2H),4.15(s,6H),3.89(t,J＝5.3Hz,2H),3.55(t,J＝4.7Hz,2H),3.38(t,J＝4.7Hz,2H),3.17(s,3H).HRMS(ESI):m/z:[M]+calc:660.1984，found:660.1972.
Example 10
Synthesis of target compounds 6, 16:
Figure BDA0002584697960000121
dissolving the compound D, 2,3,4, 5-tetrafluorodiphthalonitrile and cesium carbonate in N, N-dimethylformamide solution, and stirring at 80 ℃ for 3 h. Compound 6 was obtained as a pale grey solid powder in 23% yield.
1H NMR(600MHz,DMSO-d6)δ8.05(dd,J＝6.9,1.8Hz,1H),7.78(dd,J＝7.4,1.6Hz,1H),7.56–7.52(m,1H),7.29(qd,J＝6.8,6.4,2.1Hz,2H),7.24(s,1H),6.95(s,1H),6.87–6.81(m,2H),6.20–6.15(m,1H),4.64(t,J＝5.4Hz,2H),4.14(s,4H),4.06(s,3H),4.04–3.98(m,2H),3.68(q,J＝4.4Hz,2H),3.52(t,J＝4.7Hz,2H),3.28(s,3H).HRMS(ESI):m/z:[M]+calc:1134.4049，found:1134.4065.
Compound 16 was obtained as a brown solid powder in 32% yield.
1H NMR(600MHz,DMSO-d6)δ8.05(dd,J＝6.9,1.8Hz,1H),7.78(dd,J＝7.4,1.6Hz,1H),7.56–7.52(m,1H),7.29(qd,J＝6.8,6.4,2.1Hz,2H),7.24(s,1H),6.95(s,1H),6.87–6.81(m,2H),6.20–6.15(m,1H),4.64(t,J＝5.4Hz,2H),4.14(s,4H),4.06(s,3H),4.04–3.98(m,2H),3.68(q,J＝4.4Hz,2H),3.52(t,J＝4.7Hz,2H),3.28(s,3H).HRMS(ESI):m/z:[M]+calc:1134.4049，found:1134.4065.
Example 11
Synthesis of target compound 7:
Figure BDA0002584697960000131
a method for producing compound 7 is the same as that of compound 1.
1H NMR(600MHz,DMSO-d6)δ8.26–8.20(m,2H),8.02(s,2H),7.76(d,J＝8.0Hz,2H),7.48(td,J＝7.6,1.4Hz,2H),7.44(td,J＝7.4,1.1Hz,2H),7.26(s,2H),4.16(s,6H),4.12(t,J＝5.1Hz,2H),1.64(tt,J＝7.7,5.0Hz,2H),1.29(dpd,J＝5.8,4.2,1.9Hz,2H),0.92–0.84(m,2H),0.78(td,3H).
Example 12
Synthesis of target compound 8:
Figure BDA0002584697960000132
the method for producing compound 8 is the same as that for compound 1.
1H NMR(600MHz,DMSO-d6)δ8.23(d,J＝7.7Hz,2H),8.02(s,1H),7.83(d,J＝8.0Hz,2H),7.82–7.78(m,2H),7.77(d,J＝7.5Hz,1H),7.65(t,J＝7.6Hz,2H),7.45(t,J＝7.6Hz,2H),7.25(t,J＝7.4Hz,2H),6.97(s,2H),3.96(s,6H).
Example 13
Synthesis of target compound 9:
Figure BDA0002584697960000141
dissolving 2, 7-dimethoxycarbazole, bromobenzene, cuprous iodide and potassium carbonate in xylene in sequence, reacting for 3h at 130 ℃, and obtaining a compound 1 in the subsequent preparation step to obtain a compound 9.
1H NMR(600MHz,DMSO-d6)δ8.13(d,J＝7.7Hz,2H),8.02(s,1H),7.73(d,J＝8.0Hz,2H),7.62–7.68(m,2H),7.57(d,J＝7.5Hz,1H),7.55(t,J＝7.6Hz,2H),7.55(t,J＝7.6Hz,2H),7.25(t,J＝7.4Hz,2H),6.97(s,2H),3.96(s,6H).
Example 14
Synthesis of target compound 10:
Figure BDA0002584697960000142
the method for producing compound 10 is the same as that for compound 9.
1H NMR(600MHz,DMSO-d6)δ8.26–8.20(m,1H),8.02(s,1H),7.76(d,J＝8.0Hz,1H),7.48(td,J＝7.6,1.4Hz,1H),7.44(td,J＝7.4,1.1Hz,1H),7.26(s,1H),7.09(d,J＝7.5Hz,1H),6.71(d,J＝7.5Hz,1H),4.17(s,3H),2.87(q,J＝8.1Hz,2H),1.30(t,J＝8.0Hz,3H).
Example 15
Synthesis of target compound 11:
Figure BDA0002584697960000151
the method for producing compound 11 is a method for synthesizing compound 3.
1H NMR(600MHz,DMSO-d6)δ8.08(d,J＝7.7Hz,2H),8.01(s,1H),7.73(d,J＝8.0Hz,2H),7.62–7.68(m,2H),7.57(d,J＝7.5Hz,1H),7.55(t,J＝7.6Hz,2H),7.55(t,J＝7.6Hz,2H),7.25(t,J＝7.4Hz,2H),6.97(s,2H),3.96(s,6H),3.65(s,6H).
Example 16
Synthesis of target compound 12:
Figure BDA0002584697960000152
taking the compound 8 and potassium hydroxide, and adding ethanol and water in a volume ratio of 1: 1 at 60 ℃ to obtain the compound 12 with the yield of 88%.
1H NMR(600MHz,DMSO-d6)δ11.34(s,1H),8.26–8.20(m,2H),8.02(s,2H),7.76(d,J＝8.0Hz,2H),7.48(td,J＝7.6,1.4Hz,2H),7.44(td,J＝7.4,1.1Hz,2H),7.26(s,2H).
Example 17
Synthesis of target compound 13:
Figure BDA0002584697960000161
and (3) sequentially dissolving the compound D, 5-bromothiophene-2-ethyl formate, cuprous iodide and potassium carbonate in o-xylene, and reacting for 3 hours at 130 ℃ to obtain a compound 13 which is light yellow solid powder with the yield of 75%.
1H NMR(600MHz,DMSO-d6)δ9.69(s,1H),8.33(d,J＝7.5Hz,1H),8.07(d,J＝7.7Hz,1H),7.89(d,J＝8.0Hz,1H),7.67(s,2H),7.45(t,J＝7.6Hz,1H),7.41(t,J＝7.4Hz,1H),7.34(s,1H),7.27(d,J＝7.9Hz,1H),7.20(t,J＝7.5Hz,1H),7.09(t,J＝7.4Hz,1H),7.04(s,1H),4.77(t,J＝5.5Hz,2H),4.21(s,3H),4.14(s,3H),4.03(q,J＝7.1Hz,2H),3.96(t,J＝5.5Hz,2H),3.56(t,J＝4.7Hz,2H),3.39(dd,J＝5.7,3.7Hz,2H),3.15(s,3H),1.04(t,J＝7.1Hz,3H).13C NMR(151MHz,DMSO)δ161.17,154.62,153.38,149.49,141.83,141.36,140.85,138.56,135.97,135.21,132.85,128.74,125.45,124.84,124.14,123.10,123.04,122.72,122.03,121.17,119.19,111.66,110.56,109.11,105.93,101.29,100.06,88.70,84.70,71.78,70.29,69.47,61.15,58.45,56.29,55.97,43.96,14.32.HRMS(ESI):m/z:[M+Na]+calc:684.2144，found:684.2138.
Example 18
Synthesis of target Compound 14
Figure BDA0002584697960000171
Taking the compound D and a 60% sodium hydride kerosene mixture, adding 15mL of anhydrous tetrahydrofuran, stirring to uniformly dissolve the powder, and stirring for 1h at 50 ℃. Then 1-bromo-2- (2-methoxyethoxy) ethane is added for reaction for 3 h. Compound 14 was obtained as a grayish brown solid powder with a yield of 81%.
1H NMR(600MHz,DMSO-d6)δ8.22(d,J＝7.8Hz,2H),7.71(d,J＝8.1Hz,2H),7.39–7.34(m,2H),7.24(t,J＝7.4Hz,2H),7.11(s,2H),5.30(dt,J＝14.4,7.0Hz,2H),4.85(dt,J＝14.8,5.5Hz,2H),4.74(qt,J＝15.3,5.7Hz,2H),4.16(s,7H),3.92(td,J＝5.5,2.3Hz,2H),3.56(q,J＝4.4Hz,2H),3.40(t,J＝4.7Hz,2H),3.17(s,3H),3.06(ddd,J＝10.9,6.6,4.6Hz,2H),2.94(dt,J＝10.5,6.8Hz,2H),2.72(s,6H),2.72(s,4H),2.62(dt,J＝5.8,4.1Hz,4H).13C NMR(151MHz,DMSO)δ154.08,141.38,140.77,138.57,133.46,132.78,132.40,132.39,125.40,123.31,121.83,120.48,111.58,107.89,100.04,85.99,71.79,70.83,70.29,69.46,69.17,67.01,58.46,57.94,56.08.HRMS(ESI):m/z:[M+Na]+calc:734.3417，found:734.3418.
Example 19
Synthesis of target Compound 15
Figure BDA0002584697960000172
Dissolving the compound D, 2,3,5, 6-tetrafluoroterephthalonitrile and cesium carbonate in an N, N-dimethylformamide solution, and stirring at 80 ℃ for 3 hours to obtain a compound 6 which is a grey solid powder with the yield of 32%.
1H NMR(600MHz,DMSO-d6)δ8.05(dd,J＝6.9,1.8Hz,1H),7.78(dd,J＝7.4,1.6Hz,1H),7.56–7.52(m,1H),7.29(qd,J＝6.8,6.4,2.1Hz,2H),7.24(s,1H),6.95(s,1H),6.87–6.81(m,2H),6.20–6.15(m,1H),4.64(t,J＝5.4Hz,2H),4.14(s,4H),4.06(s,3H),4.04–3.98(m,2H),3.68(q,J＝4.4Hz,2H),3.52(t,J＝4.7Hz,2H),3.28(s,3H).HRMS(ESI):m/z:[M]+calc:1134.4049，found:1134.4065.
Example 20
Fluorescence detection
Adding 12 μ L of compound with concentration of 20mM into 2000 μ L of solvent such as dimethyl sulfoxide, methanol, tetrahydrofuran, ethyl acetate, dichloromethane, toluene, cyclohexane, etc., setting the spectrum range at 310 nm-650 nm, and the excitation wavelength at 300nm to obtain the fluorescence emission full-spectrum of compound 1 in different solvents (FIG. 1, FIG. 2). In a solvent with higher polarity than toluene, the fluorescence intensity of the compound at the short wavelength (300nm-450nm) is higher, while the fluorescence intensity at the long wavelength (at 500-600 nm) is weaker, but in the environment with lower polarity and toluene, the fluorescence intensity at the long wavelength is obviously enhanced, and the compound has reverse lyotropic discoloration effect and can be used as a chemical sensor in a solvent environment.
Example 21
Fluorescence detection
The fluorescence curves of Compound 1 were measured at different temperatures, i.e., a high temperature (60 ℃ C.), a room temperature (25 ℃ C.) and a low temperature (10 ℃ C.), in a toluene solution and a mixed solvent of toluene and tetrahydrofuran at a volume ratio of 1:1, with a spectrum of 310nm to 650nm and an excitation wavelength of 300nm (FIG. 3). With the rise of temperature, the fluorescence intensity of the compound 1 at the short wavelength is reduced, the fluorescence intensity of the compound at the long wavelength is enhanced, and the compound has a thermochromic effect and can be used as a temperature-sensitive chemical sensor.
Example 22
TABLE 1 fluorescence Performance test data for Compounds 1-16
Figure BDA0002584697960000181
Figure BDA0002584697960000191
Example 23
Crystal structure of Compound 1
The compound (110 mg) was dissolved in a nuclear magnetic tube using 5mL of a dichloromethane solution, and 5mL of a methanol solution was added slowly to the upper layer of the solution, and the solution was left to stand in a wide space, and while the solvent was slowly volatilized, the methanol layer was slowly diffused into the dichloromethane layer to decrease the solubility in the solution, thereby precipitating crystals (FIG. 4). The molecular structure shows a V-shaped conformation, the dihedral angle between the plane of the (4, 5-dicyano) phenyl group and the plane of the carbazolodiindole ring is 121.8 degrees (58.2 degrees), the (4, 5-dicyano) phenyl group can freely rotate around a C-N bond, the spatial conformation of the molecule is not fixed, but the single crystal structure shows that the distance between two hydrogen atoms adjacent to the carbazolodiindole ring and the (4, 5-dicyano) phenyl group is the same
Figure BDA0002584697960000192
Showing that a strong steric hindrance effect exists between the two.
Example 24
Fluorescence detection for interaction of sensing probes with double-stranded ds 16DNA
The spectrum was set to 315nm to 620nm, and 1900. mu.L of a PBS buffer solution (pH 7.25 to 7) was added to the cuvette35), adding 8. mu.L of compound 1(DMSO as a solvent) at a concentration of 5mM, 80. mu.L of DMSO to give a final concentration of 20. mu.M, and gradually adding ds 16DNA, [ C ] ds 16DNA/CCompound (I)]0, 0.1, 0.2, 0.3, 0.5, 0.7, 1.5 and 2.3 in sequence, with the addition of ds16 DNA, the peak at 560nm decreased slightly and the peak at 375nm increased, giving a fluorescence change pattern (see FIG. 5).
DNA sequence listing
Figure BDA0002584697960000201
Meaning of the symbols in the table: a- - -adenine; g- - -guanine; c-cytosine; t- - -thymine

Claims (10)

1. A 2, 7-dimethoxycarbazole-fused compound represented by the general formula (1), (2), (3) or (4):
Figure FDA0002584697950000011
wherein the content of the first and second substances,
r is hydrogen, 6-10 membered aryl, 5-10 membered heterocyclyl, 5-10 membered heteroaryl, C1-C10 alkyl, C1-C10 alkoxy, said heterocyclyl or heteroaryl contains 1-3 heteroatoms N, O or S, said R may be substituted by one or more substituents being C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkoxy substituted by C1-C4 alkyl, C1-C4 acyl;
R1hydrogen, halogen, hydroxyl, C1-C4 aldehyde group, carboxyl, C1-C6 ester group, C1-C10 alkyl, C1-C10 alkoxy;
R2hydrogen, halogen, hydroxyl, C1-C4 aldehyde group, carboxyl, C1-C6 ester group, C1-C10 alkyl, C1-C10 alkoxy;
R3hydrogen, halogen, hydroxyl, C1-C4 aldehyde group, carboxyl, C1-C6 ester group, C1-C10 alkyl, C1-C10 alkoxy;
R4、R5hydrogen, halogen, cyano, C1-C6 ester group, carboxyl, C1-C4 aldehyde group, nitro, A sulfonic acid group;
R6、R7is hydrogen, C1-C10 alkyl, C1-C10 alkoxy, 6-10 membered aryl, 5-10 membered heterocyclyl, 5-10 membered heteroaryl, R6、R7May be substituted by one or more substituents selected from the group consisting of C1-C4 alkyl, C1-C4 ester substituted by C1-C4 alkyl, C1-C4 alkoxy substituted by C1-C4 alkyl, and C1-C4 acyl, wherein the heterocyclic or heteroaryl group contains 1-3 heteroatoms selected from N, O and S.
2. The 2, 7-dimethoxycarbazole-fused compound or a salt thereof as claimed in claim 1,
wherein the content of the first and second substances,
r is hydrogen, phenyl, 5-6 membered heterocyclic group, 5-6 membered heteroaryl, C1-C6 alkyl, C1-C6 alkoxy, the heterocyclic group or heteroaryl contains 1-3 heteroatoms N, O or S, the R can be substituted by one or more substituents, and the substituents are C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkyl substituted C1-C4 alkoxy, C1-C4 acyl.
3. The 2, 7-dimethoxycarbazole-fused compound or a salt thereof as claimed in claim 1 or 2,
wherein R is hydrogen, phenyl,
Figure FDA0002584697950000012
C1-C6 alkyl, C1-C6 alkoxy, wherein R can be substituted by one or more substituents, such as C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkyl-substituted C1-C4 alkoxy and C1-C4 acyl.
4. The 2, 7-dimethoxycarbazole-fused compound or a salt thereof as claimed in any one of claims 1 to 3,
wherein the content of the first and second substances,
R1hydrogen, halogen, hydroxyl, C1-C4 aldehyde group, carboxyl, C1-C6 ester group, C1-C6 alkyl, C1-C6 alkoxy;
R2hydrogen, halogen, hydroxyl, C1-C4 aldehyde group, carboxyl, C1-C6 ester group, C1-C6 alkyl, C1-C6 alkoxy;
R3is hydrogen, halogen, hydroxyl, C1-C4 aldehyde group, carboxyl, C1-C6 ester group, C1-C6 alkyl, C1-C6 alkoxy.
5. The 2, 7-dimethoxycarbazole-fused compound or salt thereof as claimed in any one of claims 1 to 4,
wherein the content of the first and second substances,
R6、R7is hydrogen, C1-C6 alkyl, C1-C6 alkoxy, phenyl, 5-6 member heterocyclic radical, 5-6 member heteroaryl, R6、R7May be substituted by one or more substituents selected from the group consisting of C1-C4 alkyl, C1-C4 ester substituted by C1-C4 alkyl, C1-C4 alkoxy substituted by C1-C4 alkyl, C1-C4 acyl, said heterocyclic or heteroaryl group containing 1-3 heteroatoms selected from N, O or S; preferably, the first and second electrodes are formed of a metal,
R6、R7is hydrogen, phenyl,
Figure FDA0002584697950000022
C1-C6 alkyl, C1-C6 alkoxy, said R6、R7Can be substituted by one or more substituents, such as C1-C4 alkyl, C1-C4 ester substituted by C1-C4 alkyl, C1-C4 alkoxy substituted by C1-C4 alkyl, and C1-C4 acyl.
6. 2, 7-dimethoxycarbazole-fused compounds having the following structure or salts thereof,
Figure FDA0002584697950000021
Figure FDA0002584697950000031
7. the process for producing a 2, 7-dimethoxycarbazole-fused compound represented by the general formula (1), (2), (3) or (4) or a salt thereof according to claim 1,
Figure FDA0002584697950000041
8. use of a 2, 7-dimethoxycarbazole-fused compound or a salt thereof as claimed in any one of claims 1 to 6 for the preparation of a chemical environment sensor or a bioluminescent probe.
9. The use of claim 8, wherein the chemical environment sensor is a sensor sensing solvents of different polarity or different temperatures.
10. The use of claim 8, wherein the bioluminescent probe is one that specifically recognizes double-stranded ds16 DNA.
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