Bithiazole: An Intriguing Electron‐Deficient Building for Plastic Electronic Applications

Abstract

The heterocyclic thiazole unit has been extensively used as electron-deficient building block in π-conjugated materials over the last decade. Its incorporation into organic semiconducting materials is particularly interesting due to its structural resemblance to the more commonly used thiophene building block, thus allowing the optoelectronic properties of a material to be tuned without significantly perturbing its molecular structure. Here, we discuss the structural differences between thiazole- and thiophene-based organic semiconductors, and the effects on the physical properties of the materials. An overview of thiazole-based polymers is provided, which have emerged over the past decade for organic electronic applications and it is discussed how the incorporation of thiazole has affected the device performance of organic solar cells and organic field-effect transistors. Finally, in conclusion, an outlook is presented on how thiazole-based polymers can be incorporated into all-electron deficient polymers in order to obtain high-performance acceptor polymers for use in bulk-heterojunction solar cells and as organic field-effect transistors. Computational methods are used to discuss some newly designed acceptor building blocks that have the potential to be polymerized with a fused bithiazole moiety, hence propelling the advancement of air-stable n-type organic semiconductors.

Synthesis of a Luminescent Arsolo[2,3-d:5,4-d′]bis(thiazole) Building Block and Comparison to Its Phosphole Analogue

“…The replacement of thiophene with the more electron deficient thiazole typically leads to alterations in the optoelectronic properties without a significant change in the molecular structure. In polymeric systems, where torsional twisting between adjacent aromatic monomers can have a significant effect on the polymer properties, this offers an interesting route to fine tune properties . This study describes the synthesis and characterization of a novel 4-phenyl-4 H -arsolo­[2,3- d :5,4- d ′]­bis­(thiazole) derivative, as well as its structural parameters as determined by X-ray crystallography.…”

“…In polymeric systems, where torsional twisting between adjacent aromatic monomers can have a significant effect on the polymer properties, this offers an interesting route to fine tune properties. 17 This study describes the synthesis and characterization of a novel 4-phenyl-4H-arsolo[2,3-d:5,4-d′]bis(thiazole) derivative, as well as its structural parameters as determined by X-ray crystallography. This information is then compared to data obtained by Baumgartner et al for the phosphole analogue, 18 using the HOMHED approach to provide an experimental answer to the debate regarding the relative aromatic character of the overall systems.…”

Retracted Article: Facile preparation of bithiazole-based material for inkjet printed light-emitting electrochemical cell

“…Expanding the conjugated system and electron density with these donor groups, it can lead to a larger bathochromic shi of the absorption maximum. 46,47 All of the three compounds are photoluminescent at room temperature, the relevant uorescence peak maximum ranges from 360 to 398 nm ( Fig. 3).…”

Dehydration Polymerization for Poly(hetero)arene Conjugated Polymers

“…During the exploration of various building blocks for the synthesis of conjugated organic materials, we became interested in the thiozole N ‐oxide motif. Our curiosity was spurred by traditional prevalence of thiazoles in conjugated organic materials . and the ease with which thiazole N ‐oxide can be selectively functionalized with conjugated units via palladium‐catalyzed C−H bond arylation reactions .…”