CN103450240B - A kind of Pyrenyl borane molecular electronic material and preparation method thereof - Google Patents
A kind of Pyrenyl borane molecular electronic material and preparation method thereof Download PDFInfo
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- CN103450240B CN103450240B CN201310395852.0A CN201310395852A CN103450240B CN 103450240 B CN103450240 B CN 103450240B CN 201310395852 A CN201310395852 A CN 201310395852A CN 103450240 B CN103450240 B CN 103450240B
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Abstract
The invention belongs to molecule electronic material field, be specifically related to a kind of Pyrenyl borane molecular electronic material and preparation method thereof.The molecule electronic material that the present invention proposes is structurally containing containing pyrenyl and pyridyl borine; The advantage of this material has two aspects: (1) has the large Π structure of planar conjugate; (2) B atom has outer unoccupied orbital, and atom N has outer lone-pair electron, and the two combines, and can make electronics movement velocity quickening in the material, potential barrier reduction, namely have higher carrier mobility.This material is starting raw material by 2,7-dibromo pyrene, 4-pyridyl bromine borine, n-Butyl Lithium and palladium charcoal, and prepared by single stage method, preparation technology is simple.
Description
Technical field
The invention belongs to molecule electronic material field, be specifically related to a kind of Pyrenyl borane molecular electronic material and preparation method thereof.
Background technology
When electron device marches towards more and more less yardstick, the conventional rectifier of dependence photoetching, the work of doping principle but faces unsurmountable defect.Because according to Rayleigh criterion, photoetching lower limit is the half of wavelength of light used.The fallen space of the wavelength of photoetching technique light source used is limited after all, and the live width of photoetching is therefore limited; And from angle of statistics, at nanoscale, the fluctuation problem of foreign atom distribution shows especially, the validity of rectifying device will be caused to ensure.If, an organic molecule possesses the performance of p-n junction, electronics (acceptor) and to the function of electronics (to body) can be realized obtaining respectively, and effectively insulate between body, acceptor, electronics only to allow from negative electrode to acceptor or to body to negative electrode, be so just expected to obtain the molecule of tool rectification characteristic.Chemically synthesis is upper says, this is not impossible, utilize substituting groups different on aroma system can increase or reduce the density of organic compound π-electron cloud, the molecule sub-cell of electron-deficient (p-type) or electron rich (N-shaped) comparatively speaking can be produced.The π-electron cloud density that electron-withdrawing substituent will make fragrant sub-cell become relatively poor, thus improve electron affinity, become a good electron donor(ED).
Material prepared by the present invention contains the groups such as pyrenyl, borine, pyridine ring and alkyl chain, and be a kind of novel molecular electronic material, its advantage is as follows: (1) has the large π structure of planar conjugate; (2) B atom has outer unoccupied orbital, and atom N has outer lone-pair electron, and the two combines, and can make electronics movement velocity quickening in the material, potential barrier reduction, namely have higher carrier mobility.(3) by regulating the chain length of alkyl to control material solubleness in the solution, making material be suitable for molecular self-assembling or LB technique, improving molecular electronic device yield rate.
Summary of the invention
The object of the invention is to propose a kind of Pyrenyl borane molecular electronic material and preparation method thereof.
The Pyrenyl borane molecular electronic material that the present invention proposes, structurally containing groups such as pyrenyl, borine, pyridine ring and alkyl chains, its structural formula is as follows::
Wherein R is the one of methyl, normal-butyl, n-hexyl, dodecyl, n-hexadecyl.
The present invention proposes following several molecule electronic material especially:
(1) two (methyl (4-pyridyl) boryl) pyrene of Chinese: 2,7-
English name: 2,7-bis (methyl (pyridin-4-yl) boryl) pyrene.
Molecular formula is C
28h
22b
2n
2, chemical structural formula is as follows:
(2) two (normal-butyl (4-pyridyl) boryl) pyrene of Chinese: 2,7-
English name: 2,7-bis (butyl (pyridin-4-yl) boryl) pyrene.
Molecular formula is C
34h
34b
2n
2, chemical structural formula is as follows:
(3) two (n-hexyl (4-pyridyl) boryl) pyrene of Chinese: 2,7-
English name: 2,7-bis (butyl (pyridin-4-yl) boryl) pyrene.
Molecular formula is C
38h
42b
2n
2, chemical structural formula is as follows:
(4) two (dodecyl (4-pyridyl) boryl) pyrene of Chinese: 2,7-
English name: 2,7-bis (dodecyl (pyridin-4-yl) boryl) pyrene.
Molecular formula is C
50h
66b
2n
2, chemical structural formula is as follows:
(5) two (n-hexadecyl (4-pyridyl) boryl) pyrene of Chinese: 2,7-
English name: 2,7-bis (hexadecyl (pyridin-4-yl) boryl) pyrene.
Molecular formula is C
50h
66b
2n
2, chemical structural formula is as follows:
The invention allows for the preparation method of such molecule electronic material, this material is starting raw material by 2,7-dibromo pyrene, 4-pyridyl bromine borine, n-Butyl Lithium and palladium charcoal, and prepared by single stage method, reaction equation is as follows:
Concrete steps are as follows:
Under nitrogen protection, in three-necked bottle, add 2,7-dibromo pyrene, 4-pyridyl bromine borine, palladium charcoal and anhydrous tetrahydro furan; be cooled to 0 DEG C, drip lithium hexane solution, drip and finish; stir, continue reaction 24 hours, be warming up to 25 DEG C; add water, concentrating under reduced pressure, add ethyl acetate; separatory, organic over anhydrous dried over sodium sulfate, filters; concentrated, solid vacuum sublimation is purified, and obtains target molecule electronic material.
Accompanying drawing explanation
Fig. 1 is Pyrenyl borane molecular electronic material structural formula.
Embodiment
The invention is further illustrated by the following examples
Embodiment 1
Under nitrogen protection, 2 are added in 500mL three-necked bottle, 7-dibromo pyrene 0.01mol, 4-pyridylmethyl bromine borine 0.021mol, 5% palladium charcoal 0.1g and anhydrous tetrahydro furan 100mL, be cooled to 0 DEG C, drip the lithium hexane solution 33mL of 1M, drip and finish, stir, continue reaction 24 hours, be warming up to 25 DEG C, add water 100mL, concentrating under reduced pressure, add ethyl acetate 300mL, separatory, organic over anhydrous dried over sodium sulfate, filter, concentrated, solid vacuum sublimation is purified, obtain 2, two (methyl (4-pyridyl) boryl) pyrene (A) of 7-, yield: 79%, fusing point: >300 DEG C, ultimate analysis: C, 82.44, H, 5.41, B, 5.35, N, 6.80, calculated value C, 82.40, H, 5.43, B, 5.30, N, 6.86, mass spectrometric measurement: m/z:408 (100.0%).
Embodiment 2
Under nitrogen protection, 2 are added in 500mL three-necked bottle, 7-dibromo pyrene 0.01mol, 4-pyridyl n-butyl bromide borine 0.021mol, 5% palladium charcoal 0.1g and anhydrous tetrahydro furan 100mL, be cooled to 0 DEG C, drip the lithium hexane solution 33mL of 1M, drip and finish, stir, continue reaction 24 hours, be warming up to 25 DEG C, add water 100mL, concentrating under reduced pressure, add ethyl acetate 300mL, separatory, organic over anhydrous dried over sodium sulfate, filter, concentrated, solid vacuum sublimation is purified, obtain 2, two (normal-butyl (4-pyridyl) boryl) pyrene (B) of 7-, yield: 62%, fusing point: >300 DEG C, ultimate analysis: C, 82.91, H, 6.98, B, 4.41, N, 5.72, calculated value C, 82.96, H, 6.96, B, 4.39, N, 5.69, mass spectrometric measurement: m/z:492 (100.0%).
Embodiment 3
Under nitrogen protection, 2 are added in 500mL three-necked bottle, 7-dibromo pyrene 0.01mol, 4-pyridyl n-hexyl bromine borine 0.021mol, 5% palladium charcoal 0.1g and anhydrous tetrahydro furan 100mL, be cooled to 0 DEG C, drip the lithium hexane solution 33mL of 1M, drip and finish, stir, continue reaction 24 hours, be warming up to 25 DEG C, add water 100mL, concentrating under reduced pressure, add ethyl acetate 300mL, separatory, organic over anhydrous dried over sodium sulfate, filter, concentrated, solid vacuum sublimation is purified, obtain 2, two (n-hexyl (4-pyridyl) boryl) pyrene (C) of 7-, yield: 54%, fusing point: >300 DEG C, ultimate analysis: C, 83.21, H, 7.74, B, 3.91, N, 5.14, calculated value C, 83.23, H, 7.72, B, 3.94, N, 5.11, mass spectrometric measurement: m/z:548 (100.0%).
Embodiment 4
Under nitrogen protection, 2 are added in 500mL three-necked bottle, 7-dibromo pyrene 0.01mol, 4-pyridyl dodecyl bromide borine 0.021mol, 5% palladium charcoal 0.1g and anhydrous tetrahydro furan 100mL, be cooled to 0 DEG C, drip the lithium hexane solution 33mL of 1M, drip and finish, stir, continue reaction 24 hours, be warming up to 25 DEG C, add water 100mL, concentrating under reduced pressure, add ethyl acetate 300mL, separatory, organic over anhydrous dried over sodium sulfate, filter, concentrated, solid vacuum sublimation is purified, obtain 2, two (dodecyl (4-pyridyl) boryl) pyrene (D) of 7-, yield: 48%, fusing point: >300 DEG C, ultimate analysis: C, 83.75, H, 9.25, B, 3.06, N, 3.94, calculated value C, 83.79, H, 9.28, B, 3.02, N, 3.91, mass spectrometric measurement: m/z:716 (100.0%).
Embodiment 5
Under nitrogen protection, 2 are added in 500mL three-necked bottle, 7-dibromo pyrene 0.01mol, 4-pyridyl n-hexadecyl bromine borine 0.021mol, 5% palladium charcoal 0.1g and anhydrous tetrahydro furan 100mL, be cooled to 0 DEG C, drip the lithium hexane solution 33mL of 1M, drip and finish, stir, continue reaction 24 hours, be warming up to 25 DEG C, add water 100mL, concentrating under reduced pressure, add ethyl acetate 300mL, separatory, organic over anhydrous dried over sodium sulfate, filter, concentrated, solid vacuum sublimation is purified, obtain 2, two (n-hexadecyl (4-pyridyl) boryl) pyrene (E) of 7-, yield: 43%, fusing point: >300 DEG C, ultimate analysis: C, 84.01, H, 9.94, B, 2.67, N, 3.38, calculated value C, 84.04, H, 9.97, B, 2.61, N, 3.38, mass spectrometric measurement: m/z:828 (100.0%).
Claims (7)
1. a Pyrenyl borane molecular electronic material, it is characterized in that this material structurally containing pyrenyl and pyridyl borine, its structural formula is as follows:
Wherein R is the one of methyl, normal-butyl, n-hexyl, dodecyl, n-hexadecyl.
2. molecule electronic material according to claim 1, is characterized in that R is methyl, and the molecular formula of material is C
28h
22b
2n
2, chemical structural formula is as follows:
The name of this compound is called: two (methyl (4-pyridyl) boryl) pyrene of 2,7-
English name is: 2,7-bis (methyl (pyridin-4-yl) boryl) pyrene.
3. molecule electronic material according to claim 1, is characterized in that R is normal-butyl, and the molecular formula of material is C
34h
34b
2n
2, chemical structural formula is as follows:
The name of this compound is called: two (normal-butyl (4-pyridyl) boryl) pyrene of 2,7-
English name is: 2,7-bis (butyl (pyridin-4-yl) boryl) pyrene.
4. molecule electronic material according to claim 1, is characterized in that R is n-hexyl, and the molecular formula of material is C
38h
42b
2n
2, chemical structural formula is as follows:
The name of this compound is called: two (n-hexyl (4-pyridyl) boryl) pyrene of 2,7-
English name is: 2,7-bis (butyl (pyridin-4-yl) boryl) pyrene.
5. molecule electronic material according to claim 1, is characterized in that R is dodecyl, and the molecular formula of material is C
50h
66b
2n
2, chemical structural formula is as follows:
The name of this compound is called: two (dodecyl (4-pyridyl) boryl) pyrene of 2,7-
English name is: 2,7-bis (dodecyl (pyridin-4-yl) boryl) pyrene.
6. molecule electronic material according to claim 1, is characterized in that R is n-hexadecyl, and the molecular formula of material is C
50h
66b
2n
2, chemical structural formula is as follows:
The name of this compound is called: two (n-hexadecyl (4-pyridyl) boryl) pyrene of 2,7-
English name is: 2,7-bis (hexadecyl (pyridin-4-yl) boryl) pyrene.
7. a preparation method for molecule electronic material as claimed in claim 1, it is characterized in that this material is starting raw material by 2,7-dibromo pyrene, 4-pyridyl bromine borine, n-Butyl Lithium and palladium charcoal, prepared by single stage method, reaction equation is as follows:
Wherein R is the one of methyl, normal-butyl, n-hexyl, dodecyl, n-hexadecyl;
Concrete steps are as follows:
Under nitrogen protection, in three-necked bottle, add 2,7-dibromo pyrene, 4-pyridyl bromine borine, palladium charcoal and anhydrous tetrahydro furan; be cooled to 0 DEG C, drip lithium hexane solution, drip and finish; stir, continue reaction 24 hours, be warming up to 25 DEG C; add water, concentrating under reduced pressure, add ethyl acetate; separatory, organic over anhydrous dried over sodium sulfate, filters; concentrated, solid vacuum sublimation is purified, and obtains target molecule electronic material.
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Citations (4)
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|---|---|---|---|---|
| CN1554127A (en) * | 2000-12-22 | 2004-12-08 | �����л��뵼������˾ | Use of boron and aluminium compounds in electronic components |
| CN101473012A (en) * | 2006-06-15 | 2009-07-01 | 东丽株式会社 | Material for light-emitting device, and light-emitting device |
| JP2011001475A (en) * | 2009-06-19 | 2011-01-06 | Toyo Ink Mfg Co Ltd | Material for organic electroluminescent element and application thereof |
| CN102933588A (en) * | 2010-04-07 | 2013-02-13 | 康奈尔大学 | Covalent organic frameworks and methods of making same |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1554127A (en) * | 2000-12-22 | 2004-12-08 | �����л��뵼������˾ | Use of boron and aluminium compounds in electronic components |
| CN101473012A (en) * | 2006-06-15 | 2009-07-01 | 东丽株式会社 | Material for light-emitting device, and light-emitting device |
| JP2011001475A (en) * | 2009-06-19 | 2011-01-06 | Toyo Ink Mfg Co Ltd | Material for organic electroluminescent element and application thereof |
| CN102933588A (en) * | 2010-04-07 | 2013-02-13 | 康奈尔大学 | Covalent organic frameworks and methods of making same |
Non-Patent Citations (1)
| Title |
|---|
| Synthesis of 2- and 2,7-Functionalized Pyrene Derivatives: An Application of Selective C-H Borylation;A.G.Crawford et al;《Chem. Eur. J.》;20120313;第18卷(第16期);第5022-5035页 * |
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