773881-47-3

Basic information

• Product Name: 1,3-DibroMo-5-dodecyl-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione
• Synonyms: 1,3-DibroMo-5-dodecyl-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione;1,3-dibromo-5-(n-dodecyl)thieno[3,4-c]pyrrole-4,6-dione
• CAS NO: 773881-47-3
• Molecular Formula: C18H25Br2NO2S
• Molecular Weight: 479.2696
• Mol File: 773881-47-3.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,3-DibroMo-5-dodecyl-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-DibroMo-5-dodecyl-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione(773881-47-3)
• EPA Substance Registry System: 1,3-DibroMo-5-dodecyl-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione(773881-47-3)

Safety Data

• Hazardous Substances Data: 773881-47-3(Hazardous Substances Data)

Usage

General Description

1,3-dibromo-5-dodecyl-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione is a chemical compound that belongs to the class of thienopyrrole derivatives. It is a heterocyclic compound containing a thiophene ring fused to a pyrrole ring, with two bromine atoms attached to the thieno ring and a dodecyl chain attached to the pyrrole nitrogen. 1,3-dibromo-5-dodecyl-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione has potential applications in organic electronics and materials science due to its unique electronic and optoelectronic properties. It has been studied for its use in organic field-effect transistors, organic photovoltaic devices, and organic light-emitting diodes. Additionally, its properties make it of interest for research in the field of organic semiconductors and materials for electronic devices.

Upstream product

• 773881-44-0 5-dodecyl-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione 
• 847053-25-2 4-dodecylcarbamoylthiophene-3-carboxylic acid 
• 6007-85-8 1H,3H-thieno[3,4-c]furan-1,3-dione 
• 4282-29-5 thiophene-3,4-dicarboxylic acid 
• 18853-32-2 3,4-dicyanothiophene 
• 124-22-1 n-Dodecylamine 

Relevant articles and documents

A Distannylated Monomer of a Strong Electron-Accepting Organoboron Building Block: Enabling Acceptor–Acceptor-Type Conjugated Polymers for n-Type Thermoelectric Applications

Acceptor–acceptor (A-A) copolymerization is an effective strategy to develop high-performance n-type conjugated polymers. However, the development of A-A type conjugated polymers is challenging due to the synthetic difficulty. Herein, a distannylated monomer of strong electron-deficient double B←N bridged bipyridine (BNBP) unit is readily synthesized and used to develop A-A type conjugated polymers by Stille polycondensation. The resulting polymers show ultralow LUMO energy levels of ?4.4 eV, which is among the lowest value reported for organoboron polymers. After n-doping, the resulting polymers exhibit electric conductivity of 7.8 S cm?1 and power factor of 24.8 μW m?1 K?2. This performance is among the best for n-type polymer thermoelectric materials. These results demonstrate the great potential of A-A type organoboron polymers for high-performance n-type thermoelectrics.

Thieno[3,4- c ]pyrrole-4,6-dione-based polymer semiconductors: Toward high-performance, air-stable organic thin-film transistors

We report a new p-type semiconducting polymer family based on the thieno[3,4-c]pyrrole-4,6-dione (TPD) building block, which exhibits good processability as well as good mobility and lifetime stability in thin-film transistors (TFTs). TPD homopolymer P1 was synthesized via Yamamoto coupling, whereas copolymers P2-P8 were synthesized via Stille coupling. All of these polymers were characterized by chemical analysis as well as thermal analysis, optical spectroscopy, and cyclic voltammetry. P2-P7 have lower-lying HOMOs than does P3HT by 0.24-0.57 eV, depending on the donor counits, and exhibit large oscillator strengths in the visible region with similar optical band gaps throughout the series (～1.80 eV). The electron-rich character of the dialkoxybithiophene counits in P8 greatly compresses the band gap, resulting in the lowest Egopt in the series (1.66 eV), but also raising the HOMO energy to -5.11 eV. Organic thin-film transistor (OTFT) electrical characterization indicates that device performance is very sensitive to the oligothiophene conjugation length, but also to the solubilizing side chain substituents (length, positional pattern). The corresponding thin-film microstructures and morphologies were investigated by XRD and AFM to correlate with the OTFT performance. By strategically varying the oligothiophene donor conjugation length and optimizing the solubilizing side chains, a maximum OTFT hole mobility of ～0.6 cm2 V-1 s-1 is achieved for P4-based devices. OTFT environmental (storage) and operational (bias) stability in ambient was investigated, and enhanced performance is observed due to the low-lying HOMOs. These results indicate that the TPD is an excellent building block for constructing high-performance polymers for p-type transistor applications due to the excellent processability, substantial hole mobility, and good device stability.

Low bandgap polymers with benzo [1,2-b:4,5-b′] dithiophene and bisthiophene-dioxopyrrolothiophene units for photovoltaic applications

New donor/acceptor polymers PBDTTPT1 and PBDTTPT2 with alternating benzodithiophene (BDT) and bisthiophene-dioxopyrrolothiophene (TPT) units were synthesized by Stille coupling reaction. The polymers had optical bandgaps of 1.78 and 1.82 eV, and HOMO energy levels of -5.30 and -5.35 eV for PBDTTPT1 and PBDTTPT2, respectively. Polymeric solar cell devices based on these copolymers as donors and PC71BM as acceptor showed the highest open circuit voltage of 0.95 V and power conversion efficiency of 2.68% under the illumination of AM 1.5, 100 mW/cm2.