151271-42-0

Basic information

• Product Name: 2,2':5',2''-Terthiophene, 5-hexyl-
• CAS NO: 151271-42-0
• Molecular Formula: C18H20S3
• Molecular Weight: 332.555
• Mol File: 151271-42-0.mol

Chemical Properties

• CAS DataBase Reference: 2,2':5',2''-Terthiophene, 5-hexyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2':5',2''-Terthiophene, 5-hexyl-(151271-42-0)
• EPA Substance Registry System: 2,2':5',2''-Terthiophene, 5-hexyl-(151271-42-0)

Safety Data

• Hazardous Substances Data: 151271-42-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Electronics Industry:
2,2':5',2''-Terthiophene, 5-hexylis used as a key material in the development of organic electronic devices due to its high charge carrier mobility and favorable electronic properties. It plays a crucial role in enhancing the performance of organic solar cells and organic field-effect transistors, contributing to the advancement of efficient and cost-effective electronic devices.

Upstream product

• 18794-77-9 2-hexylthiophene 
• 3480-11-3 5-bromo(2,2'-bithiophene) 
• 492-97-7 2,2'-Bithiophene 
• 211737-28-9 2-bromo-5-hexylthiophene 
• 1003-09-4 2-bromothiophene 
• 655249-04-0 5-bromo-5′-hexyl-2,2-bithiophene 
• 162717-58-0 2-(tri-n-butyl)stannyl-5,2'-bithiophene 
• 5713-61-1 thiophen-2-yl magnesium bromide 
• 173198-21-5 5-hexanoyl-2,2':5',2-terthiophene 
• 2051-49-2 n-hexanoic anhydride 
• 1081-34-1 2,2':5',2''-terthiophene 
• 142-61-0 Hexanoyl chloride 
• 3339-79-5 5-iodo-2,2'-bithiophene 
• 479719-88-5 2-([2,2'-bithiophen]-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Downstream Products

• 151271-43-1 α,ω-Dihexylsexithiophene 

Relevant articles and documents

Synthesis, electronic, and morphological properties of tetrahedral oligothiophenes with n-hexyl terminal groups

A series of tetrahedral oligothiophenes bearing n-hexyl groups at the α-positions of the terminal thiophene rings, (n-C6H 13(C4H2S)n)4C (Hex-TnTM; n=1-4), has been synthesized by Kosugi-Migita-Stille coupling as a key reaction. Thanks to the improved solubility afforded by the terminal n-hexyl groups, the largest homologue (n=4) was successfully obtained. Whereas the smaller derivatives (n=1, 2) were obtained as liquid substances, the larger derivatives (n=3, 4) were obtained as solids. Hex-T3 TM partially adopts syn conformations between the adjacent thiophene rings in the crystal, probably owing to the packing force. Hex-T3 TM not only appeared in the crystalline state but also the amorphous state, which was stable to up to 80 °C. Regardless of the terminal groups, the derivatives of n=2 exhibited a broad fluorescence with large Stokes shifts compared to the corresponding linear analogues, thereby suggesting the presence of intramolecular interactions between the bithiophene moieties. Interactions between terthiophene branches was also suggested in the radical cations of Hex-T3 TM by cyclic voltammetry measurements.

Syntheses and properties of oligothiophenes with cyano and hexyl groups

Syntheses of new oligothiophenes which have cyano and hexyl groups at the ends of quarter- and ter-thiophenes are described. The observations of DSC and polarizing microscopy indicate the presence of liquid-crystalline (LC) phases over a wide temperature range. The energy gaps are discussed on the basis of the absorption and photoluminescence (PL) spectra and cyclic voltammetry. Thin films of oligothiophenes fabricated by vacuum deposition are investigated by AFM and XRD measurements. Copyright

Three-dimensional tetra(oligothienyl)silanes as donor material for organic solar cells

Tetrahedral conjugated systems involving four conjugated oligothiophene chains fixed onto a central silicon node (1, 2) have been synthesized and used as donor materials in hetero-junction solar cells. Bilayer solar cells have been realized by thermal eva

Poly(α-vinyl-ω-alkyloligothiophene) side-chain polymers, synthesis, fluorescence, and morphology

The synthesis of polyvinyl polymers by radical polymerization of a-vinyl-cu-alkyl-terminated thiophene and bi-, ter-, and quaterthiophenes is reported. The photoluminescence properties of the polymers in solution and in thin film are described. In thin film, self-assembly-induced white photoluminescence was observed for poly(5-vinyl-5?-hexylquaterthiophene). For this polymer, single crystals with rectangular shape and micrometer size were obtained by drop casting from CS2. MM3 calculations on model diads and triads indicate that, on increasing the size of the side groups, van der Waals interactions promote the stacking of the pendants on the same side of the polyvinyl chain.

Molecular engineering of organic semiconductors: Design of self-assembly properties in conjugated thiophene oligomers

In order to analyze the correlation between charge transport and structural properties in conjugated oligomers, sexithiophene, 6T, was substituted by hexyl groups, both on the terminal α positions (α,ωDH6T) and as pendant groups in the β position (β,β′DH6T). Structural characterizations by X-ray diffraction show that vacuum-evaporated thin films of 6T and α,ωDH6T consist of layered structures in a monoclinic arrangement, with all-trans planar molecules standing on the substrate. When compared to 6T, α,ωDH6T is mainly characterized by a very large increase of molecular organization at the mesoscopic level, evidenced by a much longer range ordering. Electrical characterizations indicate that the conductivity of α,ωDH6T is largely anisotropic, with a ratio of 120 in favor of the conductivity parallel to the substrate plane, i.e. along the stacking axis. The charge carrier mobility, determined on field-effect transistors fabricated from these conjugated oligomers, also shows an increase by a factor of 25 when passing from 6T to α,ωDH6T, reaching a value of 5 × 10-2 cm2 V-1 s-1. In contrast, β,β′DH6T presents very low conductivity and mobility, the latter being below detection limit. These results are attributed to the self-assembly properties brought by alkyl groups in the α,ω position.

One-dimensional porphyrin H-aggregates induced by solvent polarity

A series of new porphyrin derivatives possessing the side arms of alkyl-substituted thiophene oligomer were synthesized. The effects of solvent polarity on the formation of supramolecular assembly have been studied by UV-vis absorption, fluorescence emiss

Spiro[fluorene-9,9'-xanthene]-based small organic molecule hole transport material as well as preparation method and application thereof

The invention discloses an organic small molecule hole transport material based on spiro[fluorene-9,9'-xanthene]-based and a preparation method and application thereof, and the organic small moleculehole transport material takes spiro[fluorene-9,9'-xanthene] as a core, and has good amorphous form and excellent dissolving property; besides, different numbers of thiophene groups are added into sidechains, so that the material is endowed with more excellent physical and photoelectric properties through the characteristics of high electron density, excellent carrier transport capacity, controllable optical and electrochemical properties and the like; in addition, due to modification of a terminal alkyl chain, the dissolvability is improved, the film-forming property of the material is facilitated, and the material is easier to process; meanwhile, the synthesis is simple, raw materials are easy to obtain, and cost is low. The organic small molecule hole transport material is applied to anall-inorganic perovskite solar cell, and the cell efficiency of the organic small molecule hole transport material is higher than the original cell efficiency, which shows that the organic small molecule hole transport material has practical significance for improving the efficiency of the all-inorganic perovskite solar cell.

Indenothiophene-based asymmetric small molecules for organic solar cells

The development of organic semiconductors is of key importance in order to improve the performance of organic solar cells (OSCs). Three indenothiophene (IT)-containing small molecules (IT3T, ITFBT and IT2FBT) were designed and synthesized for small molecule OSCs. The thermal, optical, and electrochemical properties of the molecules were investigated. The optical bandgaps of the three small molecules are ranged from 1.80 to 2.20 eV depending on different terminal groups flanked on the IT. We study the photovoltaic performances of the three molecules by fabricating OSCs with PC71BM as an electron acceptor. Among the three molecules, ITFBF exhibited the best power conversion efficiency of 4.57% with a high open circuit voltage (VOC) of 0.98 V. We also briefly discuss structure-property guidelines for small molecules used for OSCs. The results demonstrate that IT-based small molecules are promising for small molecule OSCs with large VOCs.

Influence of structural variation on the solid-state properties of diketopyrrolopyrrole-based oligophenylenethiophenes: Single-crystal structures, thermal properties, optical bandgaps, energy levels, film morphology, and hole mobility

Five new compounds, based on diketopyrrolopyrrole (DPP) and phenylene thiophene (PT) moieties, were synthesized to investigate the effect of structural variations on solid state properties, such as single-crystal structures, optical absorption, energy lev

Efficient charge generation and collection in organic solar cells based on low band gap dyad molecules

Low band gap dyad molecules were prepared that have absorption spectra matched well with the solar spectrum, and the construction of efficient charge transport pathways was observed. Under AM 1.5 illumination, the devices have achieved the highest JSC (4.79 mA cm2) and FF (0.46) in dyad-based organic solar cells to date.