139896-65-4

Usage

Chemical structure

Two thieno[3,2-b]thiophene rings linked by ethynyl groups substituted with trimethylsilyl groups.

High electron mobility

The compound is commonly used in organic electronic materials due to its high electron mobility, making it suitable for application in organic field-effect transistors and other electronic devices.

Stability and solubility

The trimethylsilyl groups provide stability and solubility to the compound, allowing for easy processing and incorporation into various electronic devices.

Conjugated structure

The conjugated structure of the compound gives it excellent optical and electrical properties.

Promising candidate for next-generation electronic materials

Due to its high electron mobility, stability, solubility, and conjugated structure, 2,5-bis[2-(trimethylsilyl)ethynyl]thieno[3,2-b]thiophene is a promising candidate for use in next-generation electronic materials and devices.

Upstream product

• 25121-87-3 2,5-dibromothieno[3,2-b]thiophene 
• 1066-54-2 trimethylsilylacetylene 
• 937187-29-6 2,5-diiodothieno[3,2-b]thiophene 
• 251-41-2 thieno[3,2-b]thiophene 

Downstream Products

• 1431984-40-5 S,S'-[thieno[3,2-b]thiophene-2,5-diylbis(ethyne-2,1-diylbenzene-4,1-diyl)] diethanethioate 

Relevant academic research and scientific papers

Bonding and Electronic Properties of Linear Diethynyl Oligothienoacene-Bridged Diruthenium Complexes and Their Oxidized Forms

A series of five diruthenium diethynyl complexes based on α,β-fused oligothienoacenes in the core of the bridging ligands [{Ru(dppe)Cp?}2(μ-C=C-L-C=C)] [dppe = 1,2-bis(diphenylphosphino)ethane, Cp? = η5-C5Me5; L = thieno[3,2-b]thiophene (4), thieno[2,3-b]thiophene (5), 3,4-dimethylthieno[2,3-b]thiophene (6), dithieno[3,2-b:2′,3′-d]thiophene (7), and thieno[3,2-b]thieno[2′,3′:4,5]thieno[2,3-d]thiophene (8)] have been synthesized and fully characterized electrochemically and spectroscopically. Elongation of the redox noninnocent oligothienoacene bridge core causes a smaller potential difference between the initial two anodic steps, not seen for free dialkyl oligothienoacenes, and increased positive charge delocalization over the conjugated bridge backbone. The highest occupied molecular orbital of the parent complexes resides predominantly on the oligothienoacene core, with strong participation of the ethynyl linkers and slightly smaller contribution from the metallic termini. This bonding character makes the initial one-electron oxidation symmetrical, as revealed by combined voltammetric and spectroscopic (IR, UV-vis-near-IR, and electron paramagnetic resonance) methods as well as density functional theory (DFT) and time-dependent DFT calculations of truncated and selected nontruncated models of the studied series. The remarkable gradual appearance of two C=C stretching absorptions in the IR spectra of the monocationic diethynyl complexes is ascribed to increasing vibronic coupling of the IR-forbidden νs(C=C) mode of the oxidized -[C=C-core-C=C]+- bridge with a low-lying π-π?(intrabridge)/metal-to-ligand charge-transfer electronic transition in the near-to-mid-IR spectral region.

The synthesis of π-electron molecular rods with a thiophene or thieno[3,2-b]thiophene core unit and sulfur alligator clips

A series of short oligo(p-phenylene-ethynylene)- and oligo(p- phenylenevinylene)-type molecular rods with an electronically rich thiophene or thieno[3,2-b]thiophene core unit and sulfur anchoring groups (AcS-, t-BuS-) at the termini have been synthesised

Luminescent digold ethynyl thienothiophene and dithienothiophene complexes; their synthesis and structural characterisation

A series of protected and terminal dialkynes with extended π-conjugation through the fused oligothienyl linker unit in the backbone, 2,5-bis(trimethylsilylethynyl)thieno[3,2-b]thiophene 1a, 5,5′- bis(trimethylsilylethynyl)dithieno[3,2-b: 2′,3′-d]thiophene