Asymmetric benzotrichalcogenophene compound, synthesis method thereof and polymer

Patent metadata

Field	Value
Publication number	US-10093680-B2
Application number	US-201715586241-A
Country	US
Kind code	B2
Filing date	May 3, 2017
Priority date	Feb 20, 2017
Publication date	Oct 9, 2018
Grant date	Oct 9, 2018

Abstract

A synthesis method of benzotrichalcogenophene (BTC) includes using a tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) catalyst and a [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]chloro[3-phenylallyl]palladium(II) (Pd-IPr) catalyst. The asymmetric benzotrichalcogenophene compound is a heterocyclic compound having furan, thiophene, selenophene and/or tellurophene subunits.

First claim

What is claimed is:

1. A synthesis method of an asymmetric benzotrichalcogenophene compound, comprising:
mixing a first compound, a second compound, a zero-valent palladium catalyst, and a base to form a third compound, the first compound has a structure of chemical formula (2):

wherein Y is selected from the group consisting of oxygen, sulfur, selenium, tellurium, and a combination thereof,
the second compound has a structure of chemical formula (3):

wherein X is selected from the group consisting of oxygen, sulfur, selenium, and tellurium, and a combination thereof, when Y is sulfur, X is not sulfur, R 2 is —C p H 2p+1 , p is an integer of 1˜20,
the third compound has a structure of chemical formula (4):

and
mixing the third compound and a divalent palladium catalyst to form the asymmetric benzotrichalcogenophene compound.

2. The synthesis method of claim 1 , further comprising dissolving the first compound, the second compound, the zero-valent palladium catalyst and the base in an organic solvent.

3. The synthesis method of claim 1 , wherein the zero-valent palladium catalyst is tetrakis(triphenylphosphine)palladium (Pd(PPh 3 ) 4 ).

4. The synthesis method of claim 1 , wherein the base is selected from sodium carbonate or potassium carbonate.

5. The synthesis method of claim 1 , further comprising mixing the third compound and the divalent palladium catalyst in an organic solvent.

6. The synthesis method of claim 1 , wherein the divalent palladium catalyst is [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]chloro[3-phenylallyl]palladium(II) (Pd-IPr).

7. A synthesis method of an asymmetric benzotrichalcogenophene compound, comprising:
mixing a first compound, a second compound and a zero-valent palladium catalyst, the first compound has a structure of chemical formula (5):

wherein Y is selected from the group consisting of oxygen, sulfur, selenium, and tellurium and a combination thereof,
the second compound has a structure of chemical formula (6):

wherein X is selected from the group consisting of oxygen, sulfur, selenium, and tellurium, and a combination thereof, when Y is sulfur, X is not sulfur;
adding aluminium chloride and acyl chloride having a substitute group of —COC q H 2q+1 or —COOC r H 2r+1 , wherein q is an integer of 1˜12, r is an integer of 1˜12;
adding a quaternary ammonium salt to form a third compound, the third compound has a structure of chemical formula (7):

wherein R 3 is —COC q H 2q+1 or —COOC r H 2r+1 , q is an integer of 1˜12, r is an integer of 1˜12; and
mixing the third compound and a divalent palladium catalyst to form the asymmetric benzotrichalcogenophene compound.

8. The synthesis method of claim 7 , further comprising dissolving the first compound, the second compound and the zero-valent palladium catalyst in an organic solvent.

9. The synthesis method of claim 7 , wherein the zero-valent palladium catalyst is tetrakis(triphenylphosphine)palladium (Pd(PPh 3 ) 4 ).

10. The synthesis method of claim 7 , wherein the quaternary ammonium salt is tetrabutylammonium fluoride (TBAF).

11. The synthesis method of claim 7 , further comprising dissolving the third compound and the divalent palladium catalyst in an organic solvent.

12. The synthesis method of claim 7 , wherein the divalent palladium catalyst is [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]chloro[3-phenylallyl]palladium(II) (Pd-IPr).

Assignees

• Univ National Chiao Tung

Inventors

• Cheng Yen-Ju
• Pao Yu-Chieh
• Chen Shi-Yen

Classifications

• C08G61/126

  with a five-membered ring containing one sulfur atom in the ring · CPC title

• C08G2261/411

  Suzuki reactions · CPC title

• C08G2261/1412

  Saturated aliphatic units · CPC title

• C07D517/14

  Ortho-condensed systems · CPC title

• C08G2261/3243

  containing one or more sulfur atoms as the only heteroatom, e.g. benzothiophene · CPC title