Triphenyl dioxazine imide diploid derivative and preparation method thereof

Abstract

The invention discloses a triphenyl dioxazine imide diploid derivative and a preparation method thereof, and belongs to the technical field of organic synthesis. The material is a triphenyl dioxazine imide derivative with large conjugation and spatial distortion. According to the invention, monobrominated triphenyl dioxazine imide is adopted, and under catalysis of copper powder, a C-C single bond coupling method is adopted for synthesis. A triphenyl dioxazine imide diploid semiconductor material has excellent solubility in a common organic solvent, has strong absorption and high molar extinction coefficient in a visible light region, also has good oxidation-reduction characteristics and electron transmission performance, and can be applied to the field of organic photoelectricity.

Description

technical field [0001] The invention relates to a class of diploid derivatives of triphenyldioxazinimide and a preparation method thereof, belonging to the field of organic synthesis. Background technique [0002] The whole molecule of triphenyl dioxazine imide is composed of central triphenyl dioxazine skeleton and dicarboxylic acid imides on both sides. Its advantages include: strong absorption in the visible light region, high molar extinction coefficient, fluorescence quantum yield, good photostability and thermal stability, etc. It is a class of organic semiconductor materials with excellent performance. The 6-position and 14-position of triphenyldioxazinimide are affected by the electron-withdrawing groups of the imides on both sides, so the reactivity is strong, and aromatic electrophilic substitution reactions are easy to occur, and halogen can be introduced into triphenyldioxazinyl imines, a more complex chemical modification of the parent. [0003] In 2017, our r...

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Problems solved by technology

[0003] In 2017, our research group designed and synthesized a conjugated bridged triphenyldioxazinimide diploid structure, but the known triphenyldioxazinimide diploid structures all contain conjugated bridge phases. Connection, does not involve the study of triphenyldioxazinimide diploids directly connected by C-C single bonds. The diploid structure directly connected by C-C single bonds can produce steric torsion to inhibit molecular aggregation, through chemical modification of its structure , is expected to obtain N-type semiconductor materials with excellent photoelectric performance

So far, there are no diploid derivatives of triphenyldioxazine imides directly connected by C-C bonds

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