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Indenofluorene-fused ring-based A-D-A type conjugated molecule and preparation method thereof

A technology of conjugated molecules, indenofluorene nine, applied in the field of A-D-A conjugated molecules and its preparation, can solve problems such as difficult energy levels, difficult purification, weak absorption, etc., and achieve simple operation, good spectral absorption range, and strong absorption effect of ability

Inactive Publication Date: 2017-06-09
XIAN MODERN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Due to the disadvantages of this type of material such as weak absorption in the visible light region, difficulty in regulating the energy level, and difficulty in purification [Energy Environ.Sci., 2011, 4, 1558], new polymers or small molecule acceptor materials were synthesized to replace this type of material appears to be particularly necessary

Method used

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  • Indenofluorene-fused ring-based A-D-A type conjugated molecule and preparation method thereof
  • Indenofluorene-fused ring-based A-D-A type conjugated molecule and preparation method thereof
  • Indenofluorene-fused ring-based A-D-A type conjugated molecule and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] The synthetic route of embodiment 1. compound 3 is as follows:

[0029]

[0030] Under nitrogen protection, compound 1 (2.0g, 2.4mmol), compound 2 (1.3g, 6mmol), potassium carbonate (1.7g, 12mmol), 336 (0.5g), Pd(PPh 3 ) 4 (0.23g, 10% mol) was dissolved in 18mL toluene / water (5:1), heated to reflux for 72h, stopped the reaction, extracted with ether, combined organic phases, washed with saturated brine, dried over anhydrous magnesium sulfate, suction filtered, spin The solvent was dried and separated by column chromatography to obtain 1.7 g of yellow oil, with a yield of 86%. 1 H NMR (500MHz, CDCl 3 )δ7.77(s,1H),7.75(s,1H),7.64(d,J=1.8Hz,2H),7.54(d,J=1.1Hz,1H),7.52(d,J=1.1Hz, 1H), 7.50(d, J=1.6Hz, 1H), 7.48(d, J=1.6Hz, 1H), 7.44(d, J=1.4Hz, 2H), 7.25(s, 1H), 7.24(s, 1H), 3.71(s, J=1.2Hz, 6H), 2.03(t, J=8.2Hz, 9H), 1.22–1.00(m, 45H), 0.82–0.75(m, 15H). 13 C NMR (126MHz, CDCl 3)δ164.05,151.69,150.86,150.63,141.86,140.37,131.70,130.20,128.45,127.83,124.44,123.83,1...

Embodiment 2

[0031] Embodiment 2. The synthetic route of compound 4 is as follows:

[0032]

[0033] Under nitrogen protection, 10 mL of 2M butyllithium was added dropwise to a 250 mL three-neck flask containing 4-hexylbromobenzene (5.0 g, 20.7 mmol) and 100 mL of THF at -78 °C, and the reaction was kept at low temperature for 1 h. At this temperature, compound 3 (1.77 g, 2.03 mmol) was added dropwise to the reaction liquid, returned to room temperature and stirred overnight, hydrolyzed, extracted three times with ether, combined organic phases, washed with saturated brine, and dried over anhydrous magnesium sulfate. After suction filtration, the solvent was spin-dried and separated by column chromatography to obtain 0.8 g of a yellow-green oil with a yield of 80%. 1 H NMR (500MHz, CDCl 3 )δ7.64(s,1H),7.62(s,1H),7.50(d,J=3.0Hz,2H),7.32(d,J=1.6Hz,1H),7.31(d,J=1.6Hz, 1H), 7.19(d, J=8.2Hz, 8H), 7.14(t, J=6.9Hz, 8H), 7.10(d, J=5.3Hz, 2H), 6.92(d, J=1.4Hz, 2H) ,6.40(d,J=5.3Hz,2H),2.65–2.6...

Embodiment 3

[0034] Embodiment 3. The synthetic route of compound 5 is as follows:

[0035]

[0036] Add compound 4 (0.8g, 0.5mmol) into a 50mL single-necked round bottom flask, dry CH 2 Cl 2 30mL, boron trifluoride ether solution 10mL, heated under reflux to react overnight. Turn off heat. Cool, add water, CH 2 Cl 2 Extracted three times, combined the organic phases, washed with saturated brine, and dried over anhydrous magnesium sulfate. Suction filtration, spin removal of solvent, and column chromatography gave 0.57 g of yellow solid with a yield of 73%. 1 H NMR (500MHz, CDCl 3 )δ7.67(s,2H),7.44(s,2H),7.37(s,2H),7.27(s,1H),7.26(s,1H),7.21(d,J=8.3Hz,8H), 7.08(d,J=8.3Hz,8H),7.02(s,1H),7.01(s,1H),2.60–2.54(m,8H),2.06–1.91(m,9H),1.65–1.52(m, 9H),1.39–1.25(m,24H),1.19–1.00(m,40H),0.88(m,12H),0.78–0.74(m,12H),0.70(s,8H). 13 C NMR (126MHz, CDCl 3 )δ156.04,152.77,151.10,150.25,144.85,142.57,142.11,141.57,141.24,140.28,139.61,138.38,136.13,134.92,128.22,128.04,127.11,123.23,117.35,...

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Abstract

The invention belongs to the technical field of organic optoelectronic materials, and particularly relates to an indenofluorene-fused ring-based A-D-A type conjugated molecule and a preparation method thereof. The preparation method comprises the following steps: by taking indenofluorene-fused ring as a nucleus and pentabasic aromatic heterocycle as a bridged unit, connecting an end with A-D-A type conjugated molecule lacking of electronic unit. The preparation method is novel to prepare, and simple to operate, the products are easily separated and purified, and the related indenofluorene-fused ring-based A-D-A type conjugated molecule has good solubility and stability, as well as wide spectral absorption range and proper energy-level structures, and is hopefully used for donor or receptor materials of organic solar batteries.

Description

technical field [0001] The invention belongs to the field of organic photovoltaic technology, and specifically relates to a class of A-D-A conjugated molecules based on indenofluorene nona-fused rings as the mother core, five-membered aromatic heterocycles as bridging groups, and electron-deficient units connected at the ends. A preparation method, and the application of the molecule as an electron donor or an electron acceptor in the photoactive layer in the field of organic photovoltaic cells. Background technique [0002] Organic solar cells have the advantages of light weight, low cost, bendability, solution processing and large-area preparation, and have attracted the interest and attention of scientific researchers. Recently, polymer and small molecule solar cells have developed rapidly and made considerable progress [Adv. ; Nat.Commun., 2014, 5, 5293; Nature, 2014, 17, 1; J.Am.Chem.Soc. ,15027]. At present, the photoelectric conversion efficiency of bulk heterojunc...

Claims

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Application Information

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IPC IPC(8): C07D333/38C07D333/16C07D495/04H01L51/42H01L51/46
CPCC07D333/16C07D333/38C07D495/04H10K85/623H10K85/655H10K85/6576H10K30/00Y02E10/549
Inventor 郭旺军高潮刘红利张杰弥育华安忠维伍致生
Owner XIAN MODERN CHEM RES INST
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