1043023-52-4

Usage

Uses

Used in Organic Electronic Materials:
Dithieno[3,2-c:2',3'-e]oxepine-4,6-dione is utilized as an electron-accepting material for the development of organic semiconductors and light-emitting diodes. Its unique structure and properties make it a promising candidate for enhancing the performance of these devices.
Used in Organic Photovoltaic Devices:
In the field of organic photovoltaics, dithieno[3,2-c:2',3'-e]oxepine-4,6-dione is employed as a key component in the design and synthesis of novel materials. Its electron-accepting properties contribute to the improvement of the power conversion efficiency and overall performance of these solar energy conversion devices.
Used in Materials Science and Chemical Biology:
Dithieno[3,2-c:2',3'-e]oxepine-4,6-dione serves as a building block in the synthesis of functionalized organic molecules. Its versatile structure allows for the creation of new materials with tailored properties for various applications in materials science and chemical biology, including the development of new pharmaceuticals, sensors, and other advanced materials.

Upstream product

• 19690-71-2 3,3′-dicarboxylic acid-2,2′-bithiophene 
• 108-24-7 acetic anhydride 
• 51751-44-1 3,3'dibromo-2,2'-bithiophene 

Relevant academic research and scientific papers

n-channel polymers by design: Optimizing the interplay of solubilizing substituents, crystal packing, and field-effect transistor characteristics in polymeric bithiophene-imide semiconductors

Electron transporting (n-channel) polymer semiconductors for field-effect transistors are rare. In this investigation, the synthesis and characterization of new electron-depleted N-alkyl-2,2′-bithiophene-3,3′- dicarboximide-based π-conjugated homopolymers and copolymers containing the 2,2′-bithiophene unit are reported. A novel design approach is employed using computational modeling to identify favorable monomer properties such as core planarity, solubilizing substituent tailorability, and appropriate electron affinity with gratifying results. Monomeric model compounds are synthesized to confirm these properties, and a crystal structure reveals a short 3.43 A π-π stacking distance with favorable solubilizing substituent orientations. A family of 10 homopolymers and bithiophene copolymers is then synthesized via Yamamoto and Stille polymerizations, respectively. Two of these polymers are processable in common organic solvents: the homopolymer poly(N-(2-octyldodecyl)-2,2′-bithiophene-3,3′-dicarboximide) (P1) exhibits n-channel FET activity, and the copolymer poly(N-(2-octyldodecyl)-2, 2′:5′,2″:5″,2?-quaterthiophene-3, 3′-dicarboximide) (P2) exhibits air-stable p-channel FET operation. After annealing, P1 films exhibit a very high degree of crystallinity and an electron mobility > 0.01 cm2 V-1 s-1 with a current on-off ratio of 107, which is remarkably independent of film-deposition conditions. Extraordinarily, P1 films also exhibit terracing in AFM images with a step height matching the X-ray diffraction d spacing, a rare phenomenon for polymeric organic semiconductors. Another fascinating property of these materials is the air-stable p-channel FET performance of annealed P2 films, which exhibit a hole mobility of ～0.01 cm2 V-1 s-1 and a current on-off ratio of 107.

Syntheses and properties of copolymers with N-alkyl-2,2′-bithiophene-3,3′-dicarboximide unit for polymer solar cells

We report new random copolymers using the electron-deficient unit N-alkyl-2,2′-bithiophene-3,3′-dicarboximide (BTI) for organic solar cells. For absorption over a broader range of the solar spectrum, push-pull types of conjugated polymers PBTIBDT-3, PBTIBDT-5, and PBTIBDT-7, containing 4,8-bis(2-octyldodecyloxy) benzo[1,2-b;3,4-b']dithiophene (BDT) as electron-pushing unit and BTI as electron-pulling unit, were synthesized. The polymers were synthesized by coupling electron-pushing and electron-pulling units by Stille polymerization with Pd(0) catalyst. The incorporation of more BTI units induced more red shift of the absorption spectra of the polymer thin films. The device comprising PBTIBDT-5 and PC71 BM (1:1) showed VOC = 0.76 V, JSC = 3.28 mA/cm2, and fill factor (FF) = 0.51, giving a power conversion efficiency of 1.26%.