1260224-09-6

Basic information

• Product Name: 3,6-bis(5-broMo-4-(2-ethylhexyl)thiophen-2-yl)-1,2,4,5-tetrazine
• Synonyms: 3,6-bis(5-broMo-4-(2-ethylhexyl)thiophen-2-yl)-1,2,4,5-tetrazine
• CAS NO: 1260224-09-6
• Molecular Formula: C₂₆H₃₆Br₂N₄S₂
• Molecular Weight: 628.52884
• Mol File: 1260224-09-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3,6-bis(5-broMo-4-(2-ethylhexyl)thiophen-2-yl)-1,2,4,5-tetrazine(CAS DataBase Reference)
• NIST Chemistry Reference: 3,6-bis(5-broMo-4-(2-ethylhexyl)thiophen-2-yl)-1,2,4,5-tetrazine(1260224-09-6)
• EPA Substance Registry System: 3,6-bis(5-broMo-4-(2-ethylhexyl)thiophen-2-yl)-1,2,4,5-tetrazine(1260224-09-6)

Safety Data

• Hazardous Substances Data: 1260224-09-6(Hazardous Substances Data)

Usage

Uses

Used in Organic Electronics:
3,6-bis(5-bromo-4-(2-ethylhexyl)thiophen-2-yl)-1,2,4,5-tetrazine is used as a building block for the synthesis of conjugated polymers and small molecule semiconductors due to its unique electronic and optoelectronic properties.
Used in Materials Science:
3,6-bis(5-broMo-4-(2-ethylhexyl)thiophen-2-yl)-1,2,4,5-tetrazine is utilized in the development of novel materials with tailored properties for various technological applications, owing to its functional group versatility.
Used in Organic Solar Cells:
3,6-bis(5-bromo-4-(2-ethylhexyl)thiophen-2-yl)-1,2,4,5-tetrazine is used as a component in the creation of organic solar cells, contributing to their efficiency and performance.
Used in Light-Emitting Diodes (LEDs):
It serves as a material in the construction of LEDs, enhancing their light-emitting capabilities and overall performance.
Used in Field-Effect Transistors:
3,6-bis(5-bromo-4-(2-ethylhexyl)thiophen-2-yl)-1,2,4,5-tetrazine is employed in the fabrication of field-effect transistors, improving their electronic characteristics and functionality.
It is important to handle 3,6-bis(5-bromo-4-(2-ethylhexyl)thiophen-2-yl)-1,2,4,5-tetrazine with care due to its potential health and environmental hazards.

Upstream product

• 1260224-08-5 3,6-bis[4-(2-ethylhexyl)thien-2-yl]-s-tetrazine 
• 1260224-06-3 4-(2-ethylhexyl)-2-thiophenecarbaldehyde 
• 1260224-07-4 4-(2-ethylhexyl)-2-thiophenecarbonitrile 
• 121134-38-1 3-(2-ethylhexyl)thiophene 

Relevant articles and documents

Synthesis, characterization and photovoltaic applications of a low band gap polymer based on s-tetrazine and dithienosilole

A new copolymer of dithienosilole (DTS) and dithienyl-s-tetrazine (TTz), PDTSTTz, has been designed and synthesized. This solution processable polymer shows a low band gap, strong absorption and good thermal stability. Solar cells from the blend of this polymer with PC71BM showed power conversion efficiency (PCE) up to 4.2%.

The investigation of novel D-π-A type dyes (MK-3 and MK-4) for visible light driven photochemical hydrogen evolution

Two novel donor-π-acceptor (D-π-A) semiconductor organic dyes have been synthesized for the photochemical hydrogen evolution reaction (HER) to sensitize TiO2 for the first time. The molecular structures of D-π-A semiconductor organic dyes, which are entitled as MK-3 and MK-4, have been characterized by NMR spectroscopy method; and also electrochemical and optical properties have been investigated by cyclic voltammetry and UV–Vis absorption techniques, respectively. Amount of dye loading on TiO2 surface has been investigated by EDX method. The HER activities have been explored in the presence of triethanolamine (TEOA) as a electron donor reagent under sunlight (solar simulator illumination limited by cut-off filter λ ≥ 420 nm) in the absence and presence of co-catalysts (Pt and Cu2WS4). Transient photocurrent densities of MK-3/TiO2 and MK-4/TiO2 electrodes have been reached to 110 μA cm?1 and 275 μA cm?1, respectively. The photocatalytic HER activities have been relatively enhanced in the presence of the Pt or Cu2WS4 co-catalysts (dye/TiO2/Cu2WS4 or dye/TiO2/Pt) when compared to only dye/TiO2. The HER rates have been found as 427, 1277, 675, 682, 1027 and 795 μmolg?1h?1 for the MK-3/TiO2, MK-3/TiO2/Pt, MK-3/TiO2/Cu2WS4, MK-4/TiO2, MK-4/TiO2/Pt and MK-4/TiO2/Cu2WS4, respectively. The differences of photochemical activities of MK-3/TiO2 and MK-4/TiO2 have been stated taking into account dye molecule structures. Moreover, the HER mechanism have been described by using electrochemical band energy levels of dyes, TiO2 and Cu2WS4 co-catalyst.

Synthesis of novel tetrazine based D-π-A organic dyes for photoelectrochemical and photocatalytic hydrogen evolution

Two novel donor-π-acceptor (D-π-A) dyes, called as MK-2 and MK-8, are synthesized. Their structural, optical and electrochemical properties are investigated by NMR, absorption/photoluminescence spectroscopies and cyclic voltammetry techniques, respectively. Photocatalytic and photoelectrochemical hydrogen evolution properties of these D-π-A dyes are explored by using triethanolamine (TEOA) as a sacrificial electron donor under anaerobic conditions and visible light irradiation with or without co-catalysts (Cu2WS4 and Pt) for the first time. Photoelectrochemical and photocatalytic hydrogen evolution reaction (HER) activities of these dyes are studied by using TiO2 coated FTO electrodes and powdered TiO2 (Degussa P25), respectively. Photoelectrochemical response of MK-2/TiO2 and MK-8/TiO2 are figured out in the order of 180 μA cm?1 and 80 μA cm?1. The photocatalytic hydrogen evolution amounts of MK-2/TiO2, MK-2/TiO2/Cu2WS4, MK-2/TiO2/Pt, MK-8/TiO2, MK-8/TiO2/Cu2WS4 and MK-8/TiO2/Pt are turned out to be 565, 920, 1828, 374, 522 and 1260 μmolg?1h?1, respectively. Dye/TiO2 photocatalysts are displayed good stability in the both photochemical HER experiments. The alteration in the HER activities of MK-2 and MK-8 is explained by molecule structures of dyes. The proposed mechanism of photocatalytic hydrogen evolution is clarified by using electrochemical band levels of each constituent.

Alternating copolymers of dithienyl-s-tetrazine and cyclopentadithiophene for organic photovoltaic applications

As a new emerging electron deficient building block, s-tetrazine (Tz) shows high electron affinity, which is even higher than the commonly used benzothiadiazole units. This property makes Tz a very promising electron withdrawing unit for low band gap conjugated polymers, especially for organic solar cell materials. We report the synthesis and property of five alternating copolymers of s-tetrazine and cyclopenta[2,1-b:3,4-b′]dithiophene (CPDT), which are bridged with a thiophene unit. Methyl, hexyl, and/or 2-ethylhexyl groups are introduced onto thiophene and CPDT units to tune the solubility, UV absorption, frontier molecular orbital energy levels, and interchain stacking property of the resulting polymers. These polymers are stable up to 220 °C and decompose to dinitrile compounds with the breaking of Tz linkage at a higher temperature. Efficient bulk heterojunction solar cells were fabricated by blending these polymers with (6,6)-phenyl-C71-butyric acid methyl ester (PC71BM), and they reached a power conversion efficiency up to 5.53% under simulated AM 1.5 G irradiation of 100 mW/cm2. The morphological structures of the active layers from different polymers or under different processing conditions were then analyzed by atomic force microscopy (AFM) and correlated with their device performance.