Metal tin cyclized perylene diimide derivative, method for preparing the same, and method for using the same

Patent metadata

Field	Value
Publication number	US-12018041-B2
Application number	US-202017138884-A
Country	US
Kind code	B2
Filing date	Dec 30, 2020
Priority date	Dec 30, 2019
Publication date	Jun 25, 2024
Grant date	Jun 25, 2024

Abstract

A metal tin cyclized perylene diimide derivative, having a structure formula of:where R1 and R2 are each independently selected from a hydrogen atom or a group containing or not containing a substituent. The group containing or not containing a substituent is an alkyl having between 1 and 60 carbon atoms, an alkoxy having between 1 and 60 carbon atoms, a cycloalkyl having between 3 and 60 carbon atoms, an aryl having between 5 and 60 atoms, an alkylaryl having between 1 and 60 carbon atoms, an alkylheteroaryl having between 1 and 60 carbon atoms, an alkylheterocyclyl having between 1 and 60 carbon atoms, an alkyleneoxyalkyl having between 1 and 60 carbon atoms, an alkyleneoxyaryl having between 1 and 60 carbon atoms, an alkyleneoxyheteroaryl having between 1 and 60 carbon atoms, or an alkyleneoxyheterocyclyl having between 1 and 60 carbon atoms.

First claim

What is claimed is:

1. A metal tin cyclized perylene diimide derivative, having a structure formula of:

wherein
R 1 and R 2 are each independently selected from a hydrogen atom or a group containing or not containing a substituent, wherein the group containing or not containing a substituent is an alkyl having between 1 and 60 carbon atoms, an alkoxy having between 1 and 60 carbon atoms, a cycloalkyl having between 3 and 60 carbon atoms, an aryl having between 5 and 60 atoms, an alkylaryl having between 1 and 60 carbon atoms, an alkylheteroaryl having between 1 and 60 carbon atoms, an alkylheterocyclyl having between 1 and 60 carbon atoms, an alkyleneoxyalkyl having between 1 and 60 carbon atoms, an alkyleneoxyaryl having between 1 and 60 carbon atoms, an alkyleneoxyheteroaryl having between 1 and 60 carbon atoms, or an alkyleneoxyheterocyclyl having between 1 and 60 carbon atoms.

2. The metal tin cyclized perylene diimide derivative according to claim 1 , wherein
the group containing or not containing a substituent is methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, pentoxy, hexyloxy, heptoxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, tridecyloxy, tetradecyloxy, pentadecyloxy, hexadecyloxy, heptadecyloxy, octadecyloxy, nonadecyloxy, eicosyloxy, phenyl, naphthyl, anthryl, phenanthryl, tetraphenyl, pentaphenyl, hexaphenyl, pyrenyl, indenyl, biphenyl, fluorenyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, undecylcycloalkyl, dodecylcycloalkyl, tridecylcycloalkyl, tetradecylcycloalkyl, pentadecylcycloalkyl, hexadecylcycloalkyl, heptadecylcycloalkyl, octadecylcycloalkyl, nonadecylcycloalkyl, eicosylcycloalkyl, thienyl, pyrrolyl, furyl, selenyl, thirolyl, telluryl, oxazolyl, pyridyl, or pyrimidinyl containing or not containing a substituent.

3. The metal tin cyclized perylene diimide derivative according to claim 1 ,
wherein the substituent is at least one selected from the group consisting of methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, hydroxyl, sulfhydryl, fluorine atom, chlorine atom, bromine atom, iodine atom, cyano, aldehyde, esteryl, sulfonate, sulfinate, nitro, amino, imino, carboxyl, and hydrazine.

4. A method for preparing the metal tin cyclized perylene diimide derivative according to claim 1 , the method comprising:
mixing a compound A and hexa-n-butyl ditin, adding a catalyst and an organic solvent, stirring while heating a resulting mixture to carry out reaction, whereby yielding the metal tin cyclized perylene diimide derivative,

wherein R 1 and R 2 are the same as defined in claim 1 .

5. The method according to claim 4 , wherein
the heating temperature is between 90 and 180° C., a reaction time is between 1 and 30 hrs, and a dosage of hexa-n-butyl ditin is between 0.5 and 10 folds of a dosage of the compound A;
the organic solvent is one or more selected from the group consisting of benzene, toluene, xylene, chlorobenzene, dichlorobenzene, tetrahydrofuran, dioxane, nitrogen methyl pyrrolidone, dimethyl formamide, dimethyl acetamide, dimethyl sulfoxide, hexamethyl phosphoramide, sulfolane, acetonitrile, and benzonitrile; and
the catalyst is palladium acetate or tris(dibenzylideneacetone)dipalladium.

Assignees

• Univ Dalian Tech

Inventors

• Chen Lingcheng
• Zhang Wenzhong
• Xiao Yi

Classifications

• C07F7/2208 Primary

  Compounds having tin linked only to carbon, hydrogen and/or halogen · CPC title