Diboron nitride bridge-linked bipyridine and organic/ high polymer material prepared from diboron nitride bridge-linked bipyridine

A technology of bipyridine and boron nitrogen, which is applied in the field of organic/polymer solar cells, can solve the problems of sensitivity, instability of three-coordinated boron structure, and influence on material properties, and achieve good application prospects and strong π-electron delocalization , the effect of improving the migration rate

Active Publication Date: 2015-05-13
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to the unstable structure of tricoordinate boron, it is sensitive to water and oxygen.
At the same time, due to the large steric hindrance groups around it, effective stacking between molecules cannot occur.
thereby affecting the properties of the material

Method used

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  • Diboron nitride bridge-linked bipyridine and organic/ high polymer material prepared from diboron nitride bridge-linked bipyridine
  • Diboron nitride bridge-linked bipyridine and organic/ high polymer material prepared from diboron nitride bridge-linked bipyridine
  • Diboron nitride bridge-linked bipyridine and organic/ high polymer material prepared from diboron nitride bridge-linked bipyridine

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preparation example Construction

[0029] The preparation example of double boron nitrogen bridged bipyridine is as follows:

[0030] Synthesis of Compound 2 (R 1 =-C 4 h 9 ):

[0031] Under the protection of argon, dissolve 2 g of compound 1 in tetrahydrofuran, and cool to -78 ° C, slowly add 2.2 times the equivalent of n-butyllithium dropwise, and then add 3 times the equivalent of Br-C after maintaining this temperature for 2 hours. 4 h 9 , gradually warming up to 65°C and refluxing for 24 hours. Return to room temperature, evaporate the solvent to dryness, and purify by column chromatography (dichloromethane: n-hexane mobile phase) to obtain 3.5g of compound 2. 1H-NMR: (400MHz, CDCl 3 ,25℃);δ9.53(s,1H),7.85(d,J=4.0Hz,1H),7.09(m,J=8.4,4.4Hz,1H),7.01(d,J=8.3Hz,1H ), 3.18 (d, J = 12.1, 6.9 Hz, 2H), 1.75–1.68 (m, 2H), 1.52–1.45 (m, 2H), 0.98 (t, J = 7.3 Hz, 3H). 13C NMR (101MHz, CDCl 3 ,25°C): δ145.53, 140.29, 132.37, 123.05, 117.30, 42.70, 31.37, 20.67, 14.08. The synthetic route is as follows:

[00...

Embodiment 1

[0034] Synthesis of double boron nitrogen bridged bipyridine compound 5a (R 1 =-C 4 h 9 ):

[0035] Under the protection of argon, dissolve 1.5g of compound 2 in dry dichloromethane, slowly add 4 times the equivalent of boron trifluoride ether solution and a certain amount of triethylamine, reflux at 50°C for 2 hours, cool to room temperature, and distill off the solvent , purified by column chromatography (dichloromethane: n-hexane mobile phase) to obtain 1.7 g of compound 5a. 1H NMR: (400MHz, CDCl 3 ,25℃):δ8.16(d,J=4.8Hz,1H),7.57(dt,J=16.1,6.6Hz,2H),3.67–3.54(m,2H),1.70–1.62(m,2H) , 1.49–1.39 (m, 2H), 0.98 (t, J=7.2Hz, 3H). 13C NMR (101MHz, CDCl 3 ,25°C): δ143.58, 127.49, 126.46, 125.95, 122.47, 43.70, 29.98, 20.55, 14.02. Its synthetic route is as follows:

[0036]

Embodiment 2

[0038] Synthesis of double boron nitrogen bridged bipyridine compound 5b (R 1 =-C 4 h 9 ):

[0039] Under the protection of argon, dissolve 1.5 g of compound 2 in dry dichloromethane, slowly add 4 times the equivalent of triphenylboron and a certain amount of triethylamine, reflux at 50 ° C for 2 hours, cool to room temperature, distill off the solvent, and Purification by chromatographic separation (dichloromethane: n-hexane mobile phase) gave 1.8 g of compound 5b. Its synthetic route is as follows:

[0040]

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Abstract

The invention relates to diboron nitride bridge-linked bipyridine and an organic/ high polymer material prepared from the diboron nitride bridge-linked bipyridine, and belongs to the field of polymer solar cell. In order to expand the system of a receptor material, a classical pyrene unit is used as a start point and a novel BN receptor unit is developed. The diboron nitride bridge-linked bipyridine provided by the invention comprises a NB unit which has multiple advantages: such as a planar structure is favorable for the ordered close packing of the material molecules and is capable of increasing the material carrier mobility; the BN coordination interaction has a strong electron withdrawing effect for reducing the energy level of the molecule; different lengths of the alkyl chains are introduced for adjusting the solubility of the materials; the diboron nitride bridge-linked bipyridine has functional reaction site, can be used for preparing the organic/ high polymer material, and has very good application future when being applied to solar cells.

Description

technical field [0001] The invention relates to the field of organic / macromolecular solar cells, in particular to a double boron nitrogen bridged bipyridine and an organic / macromolecule material prepared therefrom. Background technique [0002] In recent years, polymer solar cells (PSCs) have been widely used and developed rapidly as emerging battery materials due to their low processing cost, good flexibility, and light weight. In the near future, it may become the main body of the world's energy supply, so it is of great significance to develop new polymer solar cells. Among them, the conjugated polymer with a donor-acceptor structure can independently change the structure of the donor unit and the acceptor unit, so as to achieve the adjustment of the energy level, band gap, solubility, and carrier mobility of the conjugated polymer. And the adjustment of phase behavior, etc., to realize the conjugated polymer photovoltaic material with narrow band gap. [0003] At prese...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C08G61/12
CPCC07F5/02C08G61/122
Inventor 刘俊窦传冬
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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