CN1394854A - Polysubstituted pyridine salt compound and its preparation method - Google Patents
Polysubstituted pyridine salt compound and its preparation method Download PDFInfo
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- CN1394854A CN1394854A CN 02112390 CN02112390A CN1394854A CN 1394854 A CN1394854 A CN 1394854A CN 02112390 CN02112390 CN 02112390 CN 02112390 A CN02112390 A CN 02112390A CN 1394854 A CN1394854 A CN 1394854A
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Abstract
The present invention relates to a kind of polysubstituted pyridine salt compound and its preparation method, belonging to a new organic compound and field of organic compound preparation technology. Said invention uses iodized N-emthyl-2,6-dimethyl or iodized N-methyl-2,4,6-trimethyl pyridine salt and aldehyde correspondent compound as raw material, and makes them produce condensation reaction under the catalytic action of alkali so as to obtain the correspondent polysubstituted pyridine salt compound. Said new compound possesses excellent nonlinear optical absorption property and several rich assembling forms.
Description
Technical field
The present invention relates to class polysubstituted pyridine salt compound and preparation method thereof, belong to new organic compound and preparing technical field thereof.
Background technology
Pyridinium derivative has superior nonlinear optical property, and possesses abundant assembling form on macroscopic view, is easy to device and practicability, so this system has demonstrated great application prospect in the nonlinear optics development.But the pyridinium salt molecular system is in non-linear absorption up to now, and especially the research of saturated absorption and anti-saturated absorption only limits to 4 mono-substituted one dimension pyridinium salt molecules on the pyridine ring.
Summary of the invention
The technical problem to be solved in the present invention is preparation one a class polysubstituted pyridine salt compound, is intended to obtain superior nonlinear optics absorbing material.Now describe content of the present invention in detail, the present invention makes this technical problem be resolved by the following technical programs: a class polysubstituted pyridine salt compound and a preparation thereof is characterized in that the structural formula of this compounds is
R '=H
R '=H
R '=H
The preparation method of R '=this compounds of H is, with iodate N-methyl-2, and 6-dimethyl or iodate N-methyl-2,4,6-trimethylpyridine salt and aldehydes corresponding compounds are raw material, and base catalysis condensation reaction takes place down makes corresponding polysubstituted pyridine salt compound, operation steps:
Iodate N-methyl-2 with 12.5～13.2 parts of weight, 6-lutidine salt or iodate N-methyl-2,4,6-trimethylpyridine salt, 20.4 the compound of correspondingization of aldehydes of～64.2 parts of weight is dissolved in the mixed solvent of trichloromethane of the methyl alcohol of 158～237 parts of weight and 0～148 part of weight, stir, refluxed 4 hours, slowly cooling, separate out solid, the solid of separating out is carried out recrystallization in the trichloromethane mixed solvent of the methyl alcohol of 474～711 parts of weight and 0～444 part of weight, behind twice in the recrystallization, obtain corresponding two of 23.1～38.2 parts of weight and replace or three substituted pyridines salt productive rate 74.2%～96.2%.
Compare with background technology, two of the inventive method preparation replaces and three substituted pyridines salt compounds have originality on molecular structure, shows significant saturated absorption and anti-saturated absorption phenomenon respectively in non-linear absorption detects.
Embodiment
Embodiment 1: one of polysubstituted pyridine salt compound, and iodate N-methyl-2,6-two
The preparation of (trans-4-methoxyl-styrene) pyridinium salt
Iodate N-methyl-2 with 12.5 parts of weight, 6-lutidine salt, 20.4 the aldehydes corresponding compounds of part weight, aubepine is dissolved in the methyl alcohol of 158 parts of weight, stir, refluxed 4 hours, slowly cooling, separate out solid,, use the methyl alcohol of 474 parts of weight at every turn solid recrystallization twice in methyl alcohol of separating out, obtain the corresponding disubstituted pyridines salt of 23.1 parts of weight behind twice recrystallization, iodate N-methyl-2,6-two (trans-4-methoxyl-styrene) pyridinium salt, productive rate 95.1%.
Embodiment 2: two of polysubstituted pyridine salt compound, and iodate N-methyl-2,6-two
The preparation of [trans-4-(N, N-dimethylamino) styryl] pyridinium salt
Iodate N-methyl-2 with 12.5 parts of weight, 6-lutidine salt, 22.4 the aldehydes corresponding compounds of part weight, the dimethylin phenyl aldehyde is dissolved in the methyl alcohol of 158 parts of weight, stir, refluxed 4 hours, slowly solid is separated out in cooling, with the solid of separating out twice in recrystallization in methyl alcohol, each methyl alcohol with 474 parts of weight, get the corresponding disubstituted pyridines salt of 24.6 parts of weight, orange red crystal iodate N-methyl-2,6-two [trans-4-(N, the N-dimethylamino) styryl] pyridinium salt, productive rate 96.2%.
Embodiment 3: three of polysubstituted pyridine salt compound, iodate N-methyl-2,6-two (trans-
The ferrocene vinyl) preparation of pyridinium salt
With the iodate N-methyl-2 of 12.5 parts of weight, 6-lutidine salt, the aldehydes corresponding compounds of 32.1 parts of weight, ferrocene formaldehyde is dissolved in the methyl alcohol of 158 parts of weight, stirs, and refluxes 4 hours, slowly cooling, separate out solid,, use the methyl alcohol of 632 parts of weight at every turn solid recrystallization twice in methyl alcohol of separating out, obtain the corresponding disubstituted pyridines salt of 30.2 parts of weight, iodate N-methyl-2,6-two (trans-ferrocene vinyl) pyridinium salt, productive rate 94.2%.
Embodiment 4: four of polysubstituted pyridine salt compound, and iodate N-methyl-2,6-two
[trans-2-(5-trans-ferrocene vinyl) thiofuran ethylene base] pyridinium salt
Preparation
Iodate N-methyl-2 with 12.5 parts of weight, 6-lutidine salt, 48.3 the aldehydes corresponding compounds of part weight, ferrocene thiofuran ethylene base formaldehyde is dissolved in the methyl alcohol of 158 parts of weight, stir, refluxed 4 hours, slowly cooling, separate out solid,, use the methyl alcohol of 474 parts of weight at every turn solid recrystallization twice in methyl alcohol of separating out, obtain the corresponding disubstituted pyridines salt of 38.2 parts of weight, iodate N-methyl-2,6-two [trans-2-(5-trans-ferrocene vinyl) thiofuran ethylene base] pyridinium salt, productive rate 89.1%.
Embodiment 5: five of polysubstituted pyridine salt compound, and iodate N-methyl-2,4,6-three
The preparation of [trans-4-(N, N-dimethylamino) styryl] pyridinium salt
Iodate N-methyl-2 with 13.2 parts of weight, 4,6-trimethylpyridine salt, 44.8 the aldehydes corresponding compounds of part weight is dissolved in the dimethylin phenyl aldehyde in the mixed solvent of trichloromethane of the methyl alcohol of 237 parts of weight and 148 parts of weight, stirs, be warming up to 80 ℃, refluxed 4 hours, slowly solid is separated out in cooling, with twice in the mixed solvent recrystallization of methyl alcohol and trichloromethane, use the methyl alcohol of 474 parts of weight and the trichloromethane of 296 parts of weight respectively at every turn, obtain the corresponding three substituted pyridines salt of 24.4 parts of weight, iodate N-methyl-2,4,6-three [trans-4-(N, N-dimethylamino) styryl] pyridinium salt, productive rate 74.2%.
Embodiment 6: six of polysubstituted pyridine salt compound, and iodate N-methyl-2,4,6-three
The preparation of (trans-4-methoxyl-styrene) pyridinium salt
Iodate N-methyl-2 with 13.2 parts of weight, 4,6-trimethylpyridine salt, 40.8 the aldehydes corresponding compounds of part weight, aubepine is dissolved in the trichloromethane mixed solvent of the methyl alcohol of 237 parts of weight and 148 parts of weight, stirs, and rises mn temperature to 80 ℃, refluxed 4 hours, slowly solid is separated out in cooling, twice in the mixed solvent recrystallization of usefulness methyl alcohol and trichloromethane, the each methyl alcohol of 474 parts of weight and trichloromethane of 296 parts of weight used respectively, obtain the corresponding three substituted pyridines salt of 25.2 parts of weight, iodate N-methyl-2,4,6-three (trans-4-methoxyl-styrene) pyridinium salt, productive rate 81.6%.
Embodiment 7: seven of polysubstituted pyridine salt compound, and iodate N-methyl-2,4,6-three
The preparation of (trans-ferrocene vinyl) pyridinium salt
Iodate N-methyl-2 with 13.2 parts of weight, 4,6-trimethylpyridine salt, 64.2 the aldehydes corresponding compounds of part weight, ferrocene formaldehyde is dissolved in the mixed solvent of trichloromethane of the methyl alcohol of 237 parts of weight and 148 parts of weight, stirs, and is warming up to 80 ℃, refluxed 4 hours, slowly solid is separated out in cooling, with the mixed solvent recrystallization of methyl alcohol and trichloromethane, the each methyl alcohol of 711 parts of weight and trichloromethane of 444 parts of weight used respectively, get the corresponding three substituted pyridines salt of 36.8 parts of weight, iodate N-methyl-2,4,6-three (trans-ferrocene vinyl) pyridinium salt, productive rate 86.4%.
The present invention is particularly useful for making polysubstituted pyridine salt compound.This compounds has good nonlinear optics absorbent properties and multiple abundant assembling form, in the nonlinear optical material field good application prospects is arranged.
Claims (1)
1. class polysubstituted pyridine salt compound and preparation method thereof is characterized in that, the structural formula of this compounds is
R '=H
R '=H
R '=H
The preparation method of R '=this compounds of H is, with iodate N-methyl-2, and 6-dimethyl or iodate N-methyl-2,4,6-trimethylpyridine salt and aldehydes corresponding compounds are raw material, and base catalysis condensation reaction takes place down makes corresponding polysubstituted pyridine salt compound, operation steps:
Iodate N-methyl-2 with 12.5～13.2 parts of weight, 6-lutidine salt or iodate N-methyl-2,4,6-trimethylpyridine salt, 20.4 the aldehydes corresponding compounds of～64.2 parts of weight is dissolved in the mixed solvent of trichloromethane of the methyl alcohol of 158～237 parts of weight and 0～148 part of weight, stir, refluxed 4 hours, slowly cooling, separate out solid, the solid of separating out is carried out recrystallization in the trichloromethane mixed solvent of the methyl alcohol of 474～711 parts of weight and 0～444 part of weight, behind twice in the recrystallization, obtain corresponding two of 23.1～38.2 parts of weight and replace or three substituted pyridines salt productive rate 74.2%～96.2%.
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| Application Number | Priority Date | Filing Date | Title |
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| CN 02112390 CN1394854A (en) | 2002-07-04 | 2002-07-04 | Polysubstituted pyridine salt compound and its preparation method |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007525441A (en) * | 2003-03-03 | 2007-09-06 | マイコソル，インコーポレイテッド | Pyridinium salts, compounds and methods of use |
| CN102558034A (en) * | 2011-06-07 | 2012-07-11 | 中国科学院福建物质结构研究所 | Organic three-order nonlinear optical material 4-(4-dimethylaminostyryl) methylpyridine trifluorosulfonate and synthesizing method thereof |
-
2002
- 2002-07-04 CN CN 02112390 patent/CN1394854A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007525441A (en) * | 2003-03-03 | 2007-09-06 | マイコソル，インコーポレイテッド | Pyridinium salts, compounds and methods of use |
| JP4742028B2 (en) * | 2003-03-03 | 2011-08-10 | マイコソル，インコーポレイテッド | Pyridinium salts, compounds and methods of use |
| CN102558034A (en) * | 2011-06-07 | 2012-07-11 | 中国科学院福建物质结构研究所 | Organic three-order nonlinear optical material 4-(4-dimethylaminostyryl) methylpyridine trifluorosulfonate and synthesizing method thereof |
| CN102558034B (en) * | 2011-06-07 | 2016-05-18 | 中国科学院福建物质结构研究所 | A kind of Developments of Third-order Nonlinear Optical Polymers 4-(4-dimethylamino styryl) picoline three fluoro sulfonates and synthetic method thereof |
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