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Fluorenyl-similar windmill-shaped nano-grid as well as preparation method and application thereof

A pinwheel-like, fluorene-like technology is applied in the field of soluble cyclic non-planar fluorene-like pinwheels and their synthesis, which can solve the problems that non-fullerene small molecule materials have not been reported, and achieve the effect of good application prospects.

Active Publication Date: 2019-03-26
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of the structures reported so far are linear molecules such as spiro rings, indenothiophene dialkyl or diaryl derivatives, and cyclopentadithiophene dialkyl or diaryl derivatives as the core accessor group. Non-planar non-fullerene small-molecule materials designed by groups, and non-planar non-fullerene small-molecule materials with non-planar closed-loop structures as the core have not yet been reported.

Method used

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  • Fluorenyl-similar windmill-shaped nano-grid as well as preparation method and application thereof
  • Fluorenyl-similar windmill-shaped nano-grid as well as preparation method and application thereof
  • Fluorenyl-similar windmill-shaped nano-grid as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] Example 1: Cyclopentadithienyl Pinwheel I

[0059]

[0060] 220ml of dried dichloromethane was added to the reaction flask, and cyclopentadithienyl tertiary alcohol-1 (0.2g, 0.42mM) was fully dissolved in a constant pressure dropping funnel filled with 200ml of dried dichloromethane, Measure boron trifluoride ether (0.1ml) with a syringe and inject it into the reaction flask, open the valve of the constant pressure dropping funnel and add it dropwise to the reaction flask, stir for 4h, until the reaction substrate is completely reacted, add water to quench and neutralize reaction. Extract with dichloromethane, combine the dichloromethane extracts of the organic phase, dry over anhydrous magnesium sulfate, filter off the desiccant, and evaporate the solvent under reduced pressure. Cyclopentadithienyl pinwheel I as a solid (0.0729 g, 38%).

[0061] 1 H NMR (400MHz, CD 3 Cl)δ7.58-7.56(d,J=7.2Hz,8H),7.37(s,4H),7.37-7.33(t,J=8.8Hz,4H),7.28-7.22(m,6H),6.84( s, 4H), 6....

Embodiment 2

[0062] Example 2: Cyclopentadithienyl Pinwheel II

[0063]

[0064] 250ml of dried dichloromethane was added to the reaction flask, and cyclopentadithienyl tertiary alcohol-2 (0.8g, 2.3mM) was fully dissolved in a constant pressure dropping funnel filled with 200ml of dried dichloromethane, Measure boron trifluoride ether (0.2ml) with a syringe and inject it into the reaction flask, open the valve of the constant pressure dropping funnel and add it dropwise into the reaction flask, stir and react for 4h, until the reaction substrate reacts completely, add water to quench and neutralize reaction. Extract with dichloromethane, combine the dichloromethane extracts of the organic phase, dry over anhydrous magnesium sulfate, filter off the desiccant, and evaporate the solvent under reduced pressure. Cyclopentadithienyl pinwheel II as a solid (0.272 g, 36%).

[0065] 1 H NMR (400MHz, CD 3 Cl)δ7.59-7.57(d,J=7.6,8H),7.40(s,4H),7.38-7.30(m,24H),7.10-7.07(dd,J=8.4,8H),6.98(s, 4H...

Embodiment 3

[0067] Electronic energy levels of cyclopentadithienyl pinwheel II were measured by electrochemical cyclic voltammetry, where Ag / AgNO 3 As reference electrode, Fc / Fc + pair as an internal reference. According to the initial oxidation potential (E ox ) and the onset reduction potential (E red ), the lowest unoccupied molecular orbital (LUMO) energy level (E LUMO ) and the highest occupied molecular orbital (HOMO) energy level (E HOMO ) can be obtained by Equation E LUMO / HOMO =-e(E red / ox +4.682) (eV) OK. (In our measurement system, the redox potential of Fc / Fc+ relative to Ag / AgNO 3 0.118V, we set the vacuum level of Fc / Fc+ to be 4.8eV. ) The LUMO and HOMO energy levels of cyclopentadithienyl pinwheel II are -3.54 and -5.85 eV, respectively.

[0068] Therefore, the fluorene-like pinwheel-like nanolattice will have a good application prospect in the field of organic solar cells.

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Abstract

The invention discloses a fluorenyl-similar windmill-shaped nano-grid as well as a preparation method and application thereof, belonging to the field of nano-techniques and organic electrons. The fluorenyl-similar windmill-shaped nano-grid is of a closed loop structure with a fluorenyl-similar micromolecule derivative as a monomer, and the structural general formula of the nano-grid is as follows:formula (shown in the description). The fluorenyl-similar windmill-shaped nano-grid is prepared through loop closing through Friedel-Crafts reaction and has the characteristics of simplicity in preparation, mild reaction condition, high productivity, yield and selectivity, simplicity and convenience in after-treatment, environmental friendliness, no toxin, regular structure, relatively good rigidity, good structural expansion property and solubility and the like; and a ring skeleton of the nano-grid contains multiple thiophene ring electron donors, and the whole structure is non-planar, so that the nano-grid has very good application prospects in the organic solar cell field after being linked with receptor groups.

Description

technical field [0001] The invention belongs to the technical field of organic semiconductor materials, and particularly relates to a soluble cyclic non-planar fluorene-based pinwheel lattice and a synthesis method and application thereof. Background technique [0002] Organic photovoltaics is one of the most basic research directions in the field of organic electronics. The research on organic solar cells (OSCs) began in 1959. After that, the research progress of organic solar cells was relatively slow. . By the early 1990s, scientists discovered that by using polymers as electron donors and fullerenes (C60) as electron acceptors, the generated excitons could be efficiently ionized and transported under light. Photovoltaic devices based on organic polymers and fullerene-like acceptors have become a new research hotspot. However, due to the insurmountable defects of fullerene acceptor materials, such as: poor stability under illumination; complex synthesis and high price; ...

Claims

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Application Information

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IPC IPC(8): C07D495/22H01L51/50H01L51/54
CPCC07D495/22H10K85/6576H10K50/00Y02E10/549
Inventor 解令海魏颖钟春晓黄维
Owner NANJING UNIV OF POSTS & TELECOMM
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