148256-63-7

Basic information

• Product Name: 2,5-DIBROMO-3-DODECYLTHIOPHENE
• Synonyms: 2,5-DIBROMO-3-DODECYLTHIOPHENE;2,5-DIBROM-3-DODECYLTHIOPHEN 97%;2, ,5-Bromo-3-dodecylthiophene;2,5-DibroMo-3-n-dodecylthiophene, 97%;2,5-Dibromo-3-laurylthiophene;2,5-DibroMo-3-dodecylthiophene,97%;DibroMo-3-dodecylthioph;Thiophene,2,5-dibroMo-3-dodecyl-
• CAS NO: 148256-63-7
• Molecular Formula: C₁₆H₂₆Br₂S
• Molecular Weight: 410.25
• Product Categories: Thiophenes;Organic Electronics and Photonics;Synthetic Tools and Reagents;Thiophene Monomers and Building Blocks;Thiophene Series
• Mol File: 148256-63-7.mol

Chemical Properties

• Boiling Point: 135 °C2.5 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.321 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.35E-05mmHg at 25°C
• Refractive Index: n20/D 1.53(lit.)
• Storage Temp.: 2-8°C
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: 2,5-DIBROMO-3-DODECYLTHIOPHENE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-DIBROMO-3-DODECYLTHIOPHENE(148256-63-7)
• EPA Substance Registry System: 2,5-DIBROMO-3-DODECYLTHIOPHENE(148256-63-7)

Safety Data

• Hazard Codes: Xi:
• Statements: R36:
• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 148256-63-7(Hazardous Substances Data)

Usage

Uses

Used in OLED Industry:
2,5-Dibromo-3-dodecylthiophene is used as an intermediate in the production of organic light-emitting diodes (OLEDs). Its chemical structure contributes to the development of electroluminescent materials that are essential for the efficient functioning of OLEDs. These devices are widely used in display technologies and lighting applications due to their high energy efficiency, thin and lightweight design, and fast response times.
Used in Flavor and Fragrance Industry:
2,5-Dibromo-3-dodecylthiophene is also utilized as an intermediate in the creation of flavor and fragrance compounds. Its unique chemical properties allow for the synthesis of a variety of complex and nuanced scents that can be used in the perfumery, cosmetics, and food industries. The compound's ability to contribute to the development of new and innovative fragrances makes it a valuable asset in these sectors.

InChI:InChI=1/C16H27BrS/c1-2-3-4-5-6-7-8-9-10-11-12-15-13-14-18-16(15)17/h13-14H,2-12H2,1H3

Upstream product

• 15890-72-9 laurylmagnesium bromide 
• 143-15-7 1-dodecylbromide 
• 104934-52-3 3-dodecylthiophene 

Downstream Products

• 1245707-29-2 1,4-bis((E)-2-(5-bromo-3-dodecylthiophen-2-yl)vinyl)benzene 
• 1299469-86-5 C₂₃H₃₃BrOS 
• 1299469-91-2 C₃₅H₅₈OS 

Relevant articles and documents

Patchy Nanofibers from the Thin Film Self-Assembly of a Conjugated Diblock Copolymer

An unexpected morphology comprising patchy nanofibers can be accessed from the self-assembly of an all-conjugated, polyselenophene-block-polythiophene copolymer. This morphology consists of very small (10 nm), polythiophene- and polyselenophene-rich domains and is unprecedented for both conjugated polymers and diblock copolymers in general. We propose that the patchy morphology occurs from the enhanced miscibility of the blocks arising from the longer alkyl chains in comparison to similar block copolymers with shorter alkyl chains, which fully phase separate, as well as the difference in rigidity between the polythiophene and polyselenophene blocks. This work demonstrates a facile way to tune the self-assembly behavior of conjugated block copolymers by modification of the side chain substituents.

Synthesis and mesophase behavior of phenylthiophene based amphiphilic molecules

Novel amphiphilic molecules consisting of a rigid 2-phenylthiophene core, with a polar flexible tri(oxylethylene) moiety attached to the phenyl ring and one or two alkyl chains attached to the thiophene ring at the other side have been synthesized by using Ni(II) and Pd(0) catalyzed coupling reaction as key steps. The tri(oxylethylene) moieties were terminated with hydroxyl group, sodium carboxylate group and lithium carboxylate group respectively. The thermotropic and solvent induced liquid crystalline behavior of these substances was investigated by polarized optical microscopy, differential scanning calorimetry and X-ray diffraction. Thereby the influence of the terminal groups attached to the tri(oxylethylene) moities as well as the influence of the length and the number of the alkyl chains on the mesophase behavior were investigated. The single alkyl chain Na-carboxylate termianted derivatives show smectic A phases, double alkyl chain Na-carboxylate terminated derivatives show a thermo tropic hexagonal columnar mesophase, while columnar mesophases are found in both single and double alkyl chain Li-carbonate terminated derivatives. The model for molecular organization in the hexagonal columnar mesophase is established.

Poly(1,4-bis((E)-2-(3-dodecylthiophen-2-yl)vinyl)benzene) for solution processable organic thin film transistor

New semiconducting polymer, poly[1,4-bis((E)-2-(5-bromo-3-dodecylthiophen- 2-yl)vinyl)benzene], was designed, synthesized and characterized. The structure of polymer was confirmed by 1H-NMR, IR and elemental analysis. The polymer was soluble in specific organic solvent. The weight-average molecular weights (MW) of polymer was found to be 11,000 with polydispersity of 1.82. UV-Visible absorption spectrum showed the maximum absorption at 428 nm (in solution) and 438 nm (in film). The highest occupied molecular orbital (HOMO) energy of the polymer is -5.36 eV by measuring cyclic voltammetry (CV). A solutionprocessed polymer thin film transistor device shows a mobility of 8.59 × 10 -4 cm2 V-1 s-1, an on/off current ratio of 2.0 × 104. Copyright

Synthesis and characterization of poly(1,4-bis((E)-2-(3dodecylthiophen-2- yl)vinyl)benzene) derivatives

New amorphous semiconducting copolymers, poly(9,9-dialkylfluorene)-alt-(3- dodecylthienyl-divinylbenzene-3dodecylthienyl) derivatives (PEFTVB and POFTVB), were designed, synthesized, and characterized. The structure of copolymers was confirmed by H NMR, IR, and elemental analysis. The copolymers showed very good solubility in organic solvents and high thermal stability with high T g of 178-185 °C. The weight average molecular weight was found to be 107,900 with polydispersity of 3.14 for PEFTVB and 76,700 with that of 3.31 for POFTVB. UV-vis absorption studies showed the maximum absorption at 428 nm (in solution) and 435 nm (in film) for PEFTVB and at 430 nm (in solution) and 436 nm (in film) for POFTVB. Photolumineseence studies showed the emission at 498 nm (in solution) and 557 nm (in film) for PEFTVB and at 498 nm (in solution) and 536 nm (in film) for POFTVB. The solution-processed thin-film transistors showed the carrier mobility of 2 × 10-4 cm2 V -1 s-1 for PEFTVB-based devices and 2 × 10 -5 cm2 V-1 s-1 for POFTVB-based devices.

Regiocontrolled synthesis of poly(3-alkylthiophenes) mediated by Rieke zinc: Their characterization and solid-state properties

A systematically regiocontrolled synthesis of poly(3-alkylthiophenes) (P3AT) mediated by Rieke zinc is reported. Rieke zinc undergoes oxidative addition to 2,5-dibromo-3-alkylthiophene or 2-bromo-5-iodo-3-alkylthiophene regioselectively to afford 2-bromo-5-(bromozincio)-3-alkylthiophene (2) or 2-bromo-5-(iodozincio)-3-alkylthiophene (10). The intermediate 2 or 10 can be polymerized catalytically to a series of regiospecific poly(3-alkylthiophenes) using different catalysts. The regioregularity of the polymer chain is solely controlled by the structure of the catalyst. An almost completely regioregular head-to-tail (HT) P3AT (4) is obtained by using Ni(DPPE)Cl2 ([1,2-bis-(diphenylphosphino)ethane]nickel(II) chloride). Use of Pd(DPPE)Cl2 leads to a reduction in the regioregularity (70: 30 HT/HH), while using Ni(PPh3)4 also leads to a much reduced regioregular P3AT (63:35 HT/HH). A totally regiorandom (50:50 HT/HH) P3AT (5) is afforded by using Pd(PPh3)4. The poly(3-butylthiophene) 4a is a 97% HT regioregular polymer. Other poly(3-alkylthiophenes) (alkyl = hexyl (4b), octyl (4c), decyl (4d), dodecyl (4e), and tetradecyl (4f)) are regioregular P3ATs with the HT linkage larger than 98.5% based on NMR analysis. Electronic absorption, X-ray diffraction, and crossed polarizing micrograph studies show that the cast films of the regioregular P3ATs (4) are self-organized, crystalline, flexible, and bronze-colored films with a metallic luster, while that of the regiorandom P3ATs (5) are amorphous and orange-colored films. The regioregular P3ATs exhibit a small bandgap (1.7 eV) which is 0.4 eV lower than that of regiorandom P3ATs (2.1 eV). Regioregular HT P3ATs have considerably improved electroconductivity and other physical properties over regiorandom P3ATs.

Synthesis and Structural Characterization of Alkyl Oligothiophenes - The First Isomerically Pure Dialkylsexithiophene

Regioselective bromination of alkylated bi- and ter-thiophenes affords key building blocks for the synthesis of higher, isomerically pure alkyl oligothiophenes.For all new compounds, unequivocal structural assignment is based on a detailed analysis of the fully coupled 13C, 1H NMR spectra.