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

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• 4282-29-5 thiophene-3,4-dicarboxylic acid 
• 847053-25-2 4-dodecylcarbamoylthiophene-3-carboxylic acid 
• 773881-44-0 5-dodecyl-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione 

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.

Synthesis and characterization of new thieno[3,4-c]pyrrole-4,6-dione derivatives for photovoltaic applications

A new class of low-bandgap copolymers based on benzodithiophene (BDT) and thieno[3,4-c]pyrrole-4,6-dione (TPD) units is reported. Chemical modifications of the conjugated backbone promote both high molecular weights and processability while allowing for tuning of the electronic properties. Copolymers with substituted thiophene spacers (alkyl chains facing the BDT unit) or unsubstituted thiophene spacers tend to have low power conversion efficiencies (PCE less than 1%) due to a bad morphology of the active layer, whereas copolymers with substituted thiophene spacers (alkyl chains facing TPD unit) show enhanced morphology and PCEs up to of 3.9%. Finally, BDT-TPD copolymers without any thiophene spacers still show the best performances with power conversion efficiencies up to 5.2%. The synthesis and characterization of new electroactive and photoactive copolymers based on benzodithiophene (BDT) and thieno[3,4-c]pyrrole-4,6-dione (TPD) units are described. The copolymers are synthesized with or without thiophene spacers in order to tune the electronic properties and to control the morphology of the active layer in bulk heterojunction solar cells. The potential of these new materials in photovoltaic devices is investigated.

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.