1884-68-0

Basic information

• Product Name: Tetraphenylthiophene
• Synonyms: 2,3,4,5-TETRAPHENYLTHIOPHENE;TETRAPHENYLTHIOPHENE;Thionessal;Tetraphenylthiophene,95%;tetraphenylthiophene:2,3,4,5-tetraphenylthiophene
• CAS NO: 1884-68-0
• Molecular Formula: C₂₈H₂₀S
• Molecular Weight: 388.52
• EINECS: 217-545-7
• Product Categories: Sulphur Derivatives
• Mol File: 1884-68-0.mol

Chemical Properties

• Melting Point: 184-185°C
• Boiling Point: 402.238 °C at 760 mmHg
• Flash Point: 147.834 °C
• Appearance: Pale yellow powder
• Density: 1.143 g/cm³
• Vapor Pressure: 2.58E-06mmHg at 25°C
• Refractive Index: 1.643
• BRN: 297707
• CAS DataBase Reference: Tetraphenylthiophene(CAS DataBase Reference)
• NIST Chemistry Reference: Tetraphenylthiophene(1884-68-0)
• EPA Substance Registry System: Tetraphenylthiophene(1884-68-0)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-37-24/25
• Hazardous Substances Data: 1884-68-0(Hazardous Substances Data)

Usage

Chemical Properties

Pale yellow powder

InChI:InChI=1/C28H20S/c1-5-13-21(14-6-1)25-26(22-15-7-2-8-16-22)28(24-19-11-4-12-20-24)29-27(25)23-17-9-3-10-18-23/h1-20H

Upstream product

• 451-40-1 phenyl benzyl ketone 
• 91-20-3 naphthalene 
• 5393-99-7 4,5-diphenyl-1,2,3-thiadiazole 
• 806-71-3 1,2,3,4-tetraphenyl-1,3-butadiene 
• 103-29-7 1,1'-(1,2-ethanediyl)bisbenzene 
• 636-04-4 N-Phenylbenzothioamide 
• 14447-41-7 (E)-1-bromo-1,2-diphenylethene 
• 13402-51-2 benzyl benzothioate 
• 98-91-9 thiobenzoic acid 
• 98-88-4 benzoyl chloride 
• 16222-10-9 1-phenyl-2-(phenylthio)ethanone 
• 139224-79-6 (3-phenylprop-2-ene-1,1-diyl)bis(phenylsulfane) 
• 100-51-6 benzyl alcohol 
• 103-82-2 phenylacetic acid 

Downstream Products

• 5271-40-9 meso-1,2,3,4-tetraphenylbutane 
• 103-29-7 1,1'-(1,2-ethanediyl)bisbenzene 
• 196-23-6 Dibenzo<2,3:10,11>perylo<1,12bcd>thiophene 
• 7641-40-9 1,1-dimethyl-2,3,4,5-tetraphenylsilole 
• 202-72-2 diphenanthro[9,10-b:9',10'-d]thiophene 
• 96216-36-3 2,5-bis(4-bromophenyl)-3,4-diphenylthiophene 
• 1314963-77-3 C₃₀H₂₂Br₂S 
• 97483-29-9 1,1'-(4,4'-(3,4-diphenylthiophene-2,5-diyl)bis(4,1-phenylene))diethanone 
• 1286232-39-0 (5,5'-(3,4-diphenylthiophene-2,5-diyl)bis(2-amino-5,1-phenylene))bis(phenylmethanone) 
• 106953-25-7 2,5-bis-[4-(2-hydroxy-naphthalen-1-ylazo)-phenyl]-3,4-diphenyl-thiophene 
• 118092-01-6 tetrakis-(4-nitro-phenyl)-thiophene 
• 97083-22-2 2,5-bis-(4-nitro-phenyl)-1,1-dioxo-3,4-diphenyl-1λ⁶-thiophene 
• 107541-96-8 2,5-bis-(4-acetylamino-phenyl)-3,4-diphenyl-thiophene 
• 97114-01-7 2-(4-nitro-phenyl)-1,1-dioxo-3,4,5-triphenyl-1λ⁶-thiophene 

Relevant articles and documents

1,4-Dithiafulvenes, Products of the Reaction of 4,4-Disubstituted 1,3-Thiazol-5(4H)-thiones and Acetylenic Compounds

On heating in toluene, 4,4-disubstituted 1,3-thiazol-5(4H)-thiones 1 and acetylenecarboxylates or acetylenecarbonitriles 2 undergo a cyclosubstitution reaction to yield 2-methylidene-1,3-dithiol derivatives 3 (1,4-dithiafulvenes) and a nitrile.Further heating of 3a and 3b in the presence of excess 2a leads to the isomeric 2,3-dihydrothiophene-2-thiones 4a and 4b, respectively.The benzodithiafulvene 14 has been formed in a similar reaction from 1a and in situ generated benzyne.

A novel synthetic approach for designing metal-free, redox-active quinoxaline-benzimidazole-based organic polymers with high energy storage capacity

New organic framework materials, namely, polyphenylquinoxaline (QOP) and polyphenylquinoxaline-benzimidazole (QOP-BOP) were designed using a high-temperature (>100 °C) polymerization reaction with different monomers, i.e., 2,5-bis-[(4-benzoylcarbonyl)phenyl]-3-4 diphenyl thiophene (BbcPDT), aromatic tetraamines and biphenyl dicarboxylic acid. The QOP-BOP copolymer exhibited specific capacitance (SC) of 305 F g-1 at the current density of 2 A g-1 and 88% retention of its initial specific capacitance after 1000 cycles, which resulted in good cyclic stability. This work establishes the first use of thiophene integrated with quinoxaline-benzimidazole units for energy storage applications and provides strategies for further developments in the performance of such conjugated materials. Cyclic voltammetry, charge-discharge and electrochemical impedance techniques were used to evaluate the electrochemical parameters, which demonstrated their potential in future energy storage devices.

Synthesis of tetraarylthiophenes by regioselective Suzuki cross-coupling reactions of tetrabromothiophene

Tetraarylthiophenes were prepared by regioselective Suzuki cross-coupling reactions of tetrabromothiophene.

Additionsreaktionen von 2-Thiazolin-5-thionen mit Acetylenen

The reaction of the 2-thiazolin-5-thiones 1 and 5, respectively, with acetylene carboxylates yields mainly 1,4-dithiafulvenes of type 3.In the presence of the acetylenic compounds, the 1,4-dithiafulvenes undergo an isomerization to give the corresponding 2,3-dihydrothiophene-2-thiones 4.

Redox-Divergent Construction of (Dihydro)thiophenes with DMSO

Thiophene-based rings are one of the most widely used building blocks for the synthesis of sulfur-containing molecules. Inspired by the redox diversity of these features in nature, we demonstrate herein a redox-divergent construction of dihydrothiophenes, thiophenes, and bromothiophenes from the respective readily available allylic alcohols, dimethyl sulfoxide (DMSO), and HBr. The redox-divergent selectivity could be manipulated mainly by controlling the dosage of DMSO and HBr. Mechanistic studies suggest that DMSO simultaneously acts as an oxidant and a sulfur donor. The synthetic potentials of the products as platform molecules were also demonstrated by various derivatizations, including the preparation of bioactive and functional molecules.

Accessing π-expanded heterocyclics beyond dibenzothiophene: Syntheses and properties of phenanthrothiophenes

A series of phenanthrothiophenes are designed and synthesized from polyarylthiophenes through regioselective Scholl reactions in one step using iron chloride as catalyst. The molecular structures of these heteroarenes displayed multiple twisted fjords, which perturb the shapes of the polycyclic frameworks to pack in slipped to near-perfect face-to-face styles in parallel or antiparallel packings. Field-effect transistor devices using single crystals of 6,12-difluorodiphenanthro[9, 10-b:9′, 10′]thiophene gave a hole mobility of 0.22 cm2 V?1 s?1.

Access to Substituted Thiophenes through Xanthate-Mediated Vinyl C(sp2)-Br Bond Cleavage and Heterocyclization of Bromoenynes

An environmentally sustainable strategy for the chemoselective heterocyclization of bromoenynes through a transition-metal-free sulfuration/cyclization process is reported. Using inexpensive and safe EtOCS2K as a thiol surrogate and tetrabutylphosphonium bromide and H2O as a mixed solvent, the reaction provided a range of substituted thiophenes in moderate to good yields. In addition, 2,3,4,5-tetrasubstituted thiophenes were able to be prepared under mild reaction conditions by electrophilic heterocyclization with NH4I and EtOCS2K in good yields.

Trisulfur Radical Anion (S3?-) Involved [1 + 2 + 2] and [1 + 3 + 1] Cycloaddition with Aromatic Alkynes: Synthesis of Tetraphenylthiophene and 2-Benzylidenetetrahydrothiophene Derivatives

S3?--mediated [1 + 2 + 2] and [1 + 3 + 1] cycloaddition reactions of aromatic alkynes to give tetraphenylthiophene and 2-benzylidenetetrahydrothiophene derivatives via two C-S bond formations are developed. These two protocols provide new, simple, and straightforward strategies to construct tetraphenylthiophene and 2-benzylidenetetrahydrothiophene derivatives under transition-metal-free conditions. This study also expands the application of S3?- in organic reactions.

Silver-Catalyzed Coupling of Two Csp3-H Groups and One-Pot Synthesis of Tetrasubstituted Furans, Thiophenes, and Pyrroles

Silver-catalyzed coupling of two Csp3-H groups to form 1,4-diketones have been developed for the first time. The resultant ketones then undergo cyclization to synthesize tetrasubstituted furans, thiophenes, and pyrroles from benzyl ketone derivatives in a one-pot reaction process. This highly-efficient synthetic method, which utilizes air as the terminal oxidant and readily accessible starting materials, displays a wide substrate scope and broad functional-group tolerance.

Thermal and spectral stability of fluorescent copolymers containing tetraphenylthiophene-quinoline unit

Fluorescent alternative copolymers containing tetraphenylthiophene- quinoline (TP-Qu) moiety were synthesized from Friedlaender reaction between o-aminoketone and acetyl groups. With the wholly aromatic-quinoline chain structure, the alternative donor-acceptor copolymers of PTPQu and PTPTPQu are rigid materials with high glass transitions (Tg = 245 and 295 °C, respectively) and with high thermal stability (with a‰&2% weight loss at 500 °C). The multiple phenyl pendant rings inherited PTPQu and PTPTPQu copolymers with good solubility in common organic solvents, which facilitate the easy fabrications of light-emitting diode (LED) devices. CV study resulted in the reversible E;bsubesub & values of 0.78 and 0.75 V for the PTPQu and PTPTPQu copolymers, respectively. With high quantum yields (φFs, = 0.59 for PTPQu and 0.74 for PTPTPQu) in the film states, the two copolymers and their devices exhibit stable photoluminescence (PL) and electroluminescence (EL) spectra, respectively, on change of annealing temperatures to at least higher than 250 °C. After annealing at 250 °C (or 300 °C), no change was observed in the respective PL and EL spectra of PTPQu (or PTPTPQu) copolymers. The results indicate that alternative copolymers containing donor-acceptor TP-Qu unit are promising candidates for LEDs with high efficiency and spectral stability.