1422391-62-5

Basic information

• Product Name: 2,5,7-tris(3-hexylthiophen-2-yl)thieno[3,4-b]pyrazine
• Synonyms: 2,5,7-tris(3-hexylthiophen-2-yl)thieno[3,4-b]pyrazine
• CAS NO: 1422391-62-5
• Molecular Weight: 635.039
• Mol File: 1422391-62-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2,5,7-tris(3-hexylthiophen-2-yl)thieno[3,4-b]pyrazine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5,7-tris(3-hexylthiophen-2-yl)thieno[3,4-b]pyrazine(1422391-62-5)
• EPA Substance Registry System: 2,5,7-tris(3-hexylthiophen-2-yl)thieno[3,4-b]pyrazine(1422391-62-5)

Safety Data

• Hazardous Substances Data: 1422391-62-5(Hazardous Substances Data)

Upstream product

• 69249-61-2 3-hexyl-2-bromothiophene 
• 272-43-5 thieno<3,4-b>pyrazine 
• 1188306-70-8 5,7-bis(3-hexylthiophen-2-yl)thieno[3,4-b]pyrazine 

Relevant articles and documents

Palladium-catalyzed direct C-H arylation of thieno[3,4-b]pyrazines: Synthesis of advanced oligomeric and polymeric materials

The first examples are reported of an efficient regioselective direct C-H arylation of thieno[3,4-b]pyrazine (TP) and its 2,3-dimethyl derivative with bromoalkylthiophenes (BATs), under Heck experimental conditions using Pd(OAc)2/Bu4NBr as the catalytic system, giving rise to a variety of valuable aryl-substituted thienopyrazines. The obtained results suggested that the 2-position of the TP moiety is less reactive towards C-H arylation than the 5-and 7-positions. Moreover, the 3-position of the TP moiety showed almost no significant reactivity when all other positions were arylated. The C-H arylation of 2,3-dimethyl-TP with an excess amount of BATs proceeded smoothly, affording the corresponding diarylated thienopyrazine derivatives in excellent yields, without any additional products. Compared to usual cross-coupling reactions, the present synthetic methodology has been used to prepare interesting donor-acceptor π-conjugated polymeric materials in a facial manner in a simple way. Microwave-assisted polymerization proved to be efficient for obtaining reasonable molecular weight copolymers ranging from 18.8 to 24.3 kg mol-1. Incorporating the thienopyrazine unit into polyhexylthiophene chains affected the photophysical and electrochemical properties. The optical band gaps were estimated to be in the range of 1.63-1.06 eV. All copolymers exhibited a diffraction peak at around 2θ = 5.72° corresponding to a d spacing of 15.43 A, which was assigned to an interchain spacing between polymer main chains similar to that found in P3HT. Moreover, a peak around 2θ = 23.09 (3.84 A) was also observed and is believed to be related to π-π stacking of the polymer backbones.