906372-08-5

Basic information

• Product Name: 4,4-di-n-hexyl-dithieno[3,2-b:2',3'-d]silole
• Synonyms: 4,4-di-n-hexyl-dithieno[3,2-b:2',3'-d]silole
• CAS NO: 906372-08-5
• Molecular Weight: 362.676
• Mol File: 906372-08-5.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 4,4-di-n-hexyl-dithieno[3,2-b:2',3'-d]silole(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4-di-n-hexyl-dithieno[3,2-b:2',3'-d]silole(906372-08-5)
• EPA Substance Registry System: 4,4-di-n-hexyl-dithieno[3,2-b:2',3'-d]silole(906372-08-5)

Safety Data

• Hazardous Substances Data: 906372-08-5(Hazardous Substances Data)

Usage

Description

4,4-di-n-hexyl-dithieno[3,2-b:2',3'-d]silole is a chemical compound characterized by its unique molecular structure, which features two fused thiophene rings and a silole core. This structure endows it with high charge carrier mobility and excellent photovoltaic properties, making it a promising candidate for the development of next-generation organic electronic materials.

Uses

Used in Organic Electronics:
4,4-di-n-hexyl-dithieno[3,2-b:2',3'-d]silole is used as a key component in organic electronics due to its high charge carrier mobility and photovoltaic properties. Its strong absorption in the visible region and solubility in common organic solvents make it suitable for solution processing techniques, which are essential for the fabrication of organic electronic devices.
Used in Organic Photovoltaic Devices:
In the field of photovoltaics, 4,4-di-n-hexyl-dithieno[3,2-b:2',3'-d]silole is used as an active layer material for organic photovoltaic devices. Its strong absorption in the visible region and desirable electronic properties contribute to the efficiency and performance of these devices, making it a valuable material for solar energy conversion.
Used in Solution Processing Techniques:
4,4-di-n-hexyl-dithieno[3,2-b:2',3'-d]silole is used as a soluble material in solution processing techniques for the fabrication of organic electronic devices. Its long alkyl side chains enhance its solubility in common organic solvents, facilitating the production of thin films and other structures necessary for device performance.

Upstream product

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• 51751-44-1 3,3'dibromo-2,2'-bithiophene 
• 18204-93-8 dichlorodi-n-hexylsilane 

Downstream Products

• 1192035-54-3 5'-{2-{4-[N,N-bis(4-(2-ethylhexyloxy)phenyl)amino]phenyl}-3,4-ethylenedioxythiophene-5-yl}-3,3'-di-n-hexylsilylene-2,2'-bithiophene-5-carbaldehyde 
• 1192035-56-5 2-cyano-3-{5'-{2-{4-[N,N-bis(4-(2-ethylhexyloxy)phenyl)amino]phenyl}-3,4-ethylenedioxythiophene-5-yl}-3,3'-di-n-hexylsilylene-2,20-bithiophene-5-yl}acrylic acid 

Relevant articles and documents

Terpyridine-based donor-acceptor metallo-supramolecular polymers with tunable band gaps: Synthesis and characterization

Three new building blocks containing the electron-donor fused-ring motifs carbazole, dithienosilole (DTS) and dithienopyrrole (DTP) and the 2,2′:6′,2″-terpyridine electron-acceptor motif were designed and synthesized. Directed by transition metal ions, the self-assembly of the building blocks triggered polymerization to form the corresponding metallo-supramolecular polymers PCzTPY, PSiTPY and PNTPY, respectively. The UV-vis absorption maxima of the building blocks occur at long wavelengths (351, 368 and 430 nm for CzTPY, SiTPY and NTPY, respectively), which arises from intramolecular charge transfer (ICT) transitions. However, the absorption maxima of their corresponding metallo-supramolecular polymers are clearly red-shifted (to 394, 431 and 509 nm for PCzTPY, PSiTPY and PNTPY, respectively), which is caused by the incorporation of the transition metal ion into the backbones of the target polymers. Based on the above strategies, the resulting metallo-polymers exhibit reduced energy gaps, which are 2.07, 1.97 and 1.56 eV for the PCzTPY, PSiTPY and PNTPY metallo-supramolecular polymers, respectively.

Synthesis, characterization, and transistor response of semiconducting silole polymers with substantial hole mobility and air stability. Experiment and theory

Realizing p-channel semiconducting polymers with good hole mobility, solution processibility, and air stability is an important step forward in the chemical manipulation of charge transport in polymeric solids and in the development of low-cost printed electronics. We report here the synthesis and full characterization of the dithienosilole- and dibenzosilole-based homopolymers, poly(4,4-di-n-hexyldithienosilole) (TS6) and poly(9,9-di-n- octyldibenzosilole) (BS8), and their mono- and bithiophene copolymers, poly(4,4-di-n-hexyldithienosilole-alt-(bi)thiophene) (TS6T1, TS6T2) and poly(9,9-di-n-octyldibenzosilole-alt-(bi)thiophene) (BS8T1,BS8T2), and examine in detail the consequences of introducing dithienosilole and dibenzosilole cores into a thiophene polymer backbone. We demonstrate air-stable thin-film transistors (TFTs) fabricated under ambient conditions having hole mobilities as large as 0.08 cm2/V·s, low turn-on voltages, and current on/off ratios > 106. Additionally, unencapsulated TFTs fabricated under ambient conditions are air-stable, an important advance over regioregular poly(3-hexylthiophene) (P3HT)-based devices. Density functional theory calculations provide detailed insight into the polymer physicochemical and charge transport characteristics. A direct correlation between the hole injection barrier and both TFT turn-on voltage and TFT polymer hole mobility is identified and discussed, in combination with thin-film morphological characteristics, to explain the observed OTFT performance trends.