5660-45-7

Basic information

• Product Name: ALPHA-QUINQUETHIOPHENE
• Synonyms: ALPHA-QUINQUETHIOPHENE;α-Quinquethiophene
• CAS NO: 5660-45-7
• Molecular Formula: C₂₀H₁₂S₅
• Molecular Weight: 412.645
• Product Categories: Functional Materials;Reagents for Conducting Polymer Research;Thiophene Derivatives (for Conduting Polymer Research)
• Mol File: 5660-45-7.mol
• Article Data: 15

Chemical Properties

• Melting Point: 253 °C
• Boiling Point: 535.2±45.0 °C(Predicted)
• Appearance: /
• Density: 1.384±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: ALPHA-QUINQUETHIOPHENE(CAS DataBase Reference)
• NIST Chemistry Reference: ALPHA-QUINQUETHIOPHENE(5660-45-7)
• EPA Substance Registry System: ALPHA-QUINQUETHIOPHENE(5660-45-7)

Safety Data

• Hazardous Substances Data: 5660-45-7(Hazardous Substances Data)

Usage

General Description

ALPHA-QUINQUETHIOPHENE is a chemical compound consisting of five thiophene rings joined together in a linear structure. It is a highly conjugated molecule, making it useful in organic electronics and materials science. ALPHA-QUINQUETHIOPHENE exhibits unique optical and electronic properties, including high absorption in the visible and near-infrared regions, as well as good charge transport characteristics. ALPHA-QUINQUETHIOPHENE has been studied for potential applications in organic semiconductors, photovoltaic devices, and organic light-emitting diodes. Its structural and electronic properties make it a promising candidate for the development of advanced materials for various technological applications.

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Relevant articles and documents

Synthesis of α-Thiophene Oligomers via 1,3-Butadiynes

Individual oligomers possessing thiophenes linked by their 2- and 5-positions are conveniently prepared via 1,3-butadiynes.These can be prepared in good yield by the Glaser symmetrical coupling of thienylacetylenes.Following the cyclization of the 1,3-butadiyne unit into a thiophene with sodium sulfide, an oligomer possessing an odd number of thiophene rings is obtained.Oligomers with an even number of rings are accessible from unsymmetrical butadiynes obtained either by the Cadiot-Chodkiewicz procedure, utilizing an odd and an even precursor, or by an organoborane co upling procedure.

Facilitated synthesis of functional oligothiophenes for application in thin film devices and live cell imaging

This paper describes recent developments in the synthesis of ultrapure functional oligothiophene-based materials taking advantage of enabling techniques such as microwave/ultrasound irradiation and chitosan-supported palladium catalysts. Examples showing how ultrapure oligothiophenes self-organize in order to optimize charge transport in thin film devices and fluorescence emission inside living cells are reported.

Pseudo five-component synthesis of 2,5-di(hetero)arylthiophenes via a one-pot Sonogashira-Glaser cyclization sequence

Based upon a consecutive one-pot Sonogashira-Glaser coupling-cyclization sequence a variety of 2,5-di(hetero)arylthiophenes were synthesized in moderate to good yields. A single Pd/Cu-catalyst system, without further catalyst addition, and easily available, stable starting materials were used, resulting in a concise and highly efficient route for the synthesis of the title compounds. This novel pseudo five-component synthesis starting from iodo(hetero)arenes is particularly suitable as a direct access to well-defined thiophene oligomers, which are of peculiar interest in materials science.

Synthesis and photovoltaic properties of formyl end-capped oligothiophenes

For the purpose of developing novel photovoltaic materials, 5,5″-biformyl-2,2′:5′,2″-terthiophene (OHC-3T-CHO) and 5,5″-biformyl-2,2′:5′,2″:5″,2?:5?, 2″″-q-uinquethiophene (OHC-5T-CHO) were synthesized. The photovoltaic properties of OHC-3T-CHO and OHC-5T-CHO were studied. We have fabricated two flexible organic photovoltaic devices using OHC-3T-CHO, OHC-5T-CHO, and 3,4,9,10-perylenetetracarboxylic dianhydride (PTCDA). The PET-ITO (indium tin oxides coated with polyethylene terephthalate)/OHC-3T-CHO/ PTCDA/Al device has an open circuit voltage (Voc) of 1.12V, and photoelectric conversion efficiency (PCE) of 1.00%, whereas the PET-ITO/OHC-5T-CHO/PTCDA/Al device has a Voc of 1.78V and PCE of 1.08%. Both devices have high Voc (1.12V and 1.78V). It is possible that intermolecular hydrogen bonding between the -CHO group of OHC-nT-CHO and the carboxylic dianhydride of PTCDA enhanced the efficiency by promoting forward interfacial electron transfer.