15509-95-2

Usage

Uses

Used in Organic Photovoltaic Devices:
1,3,5-Tri(thiophen-2-yl)benzene is used as a trifunctionalized monomer for the synthesis of conjugated C3-symmetric poly(arylbenzene) polymers. These polymeric materials are utilized in organic photovoltaic devices, where they contribute to the efficiency and performance of the solar cells by enhancing charge transport and light absorption properties.
Used in Organic Field Effect Transistors (OFETs):
In the electronics industry, 1,3,5-tri(thiophen-2-yl)benzene is used as a key component in the development of organic field effect transistors (OFETs). The synthesized polymers from this monomer improve the charge carrier mobility and stability of the transistors, making them suitable for various electronic applications, including flexible displays and sensors.
Used in Organic Light Emitting Diodes (OLED) Systems:
1,3,5-Tri(thiophen-2-yl)benzene is also employed in the production of organic light emitting diodes (OLED) systems. The polymers derived from this monomer exhibit excellent electroluminescent properties, which are crucial for the efficient operation of OLEDs in various display and lighting applications.

Upstream product

• 626-39-1 1,3,5-trisbromobenzene 
• 81745-84-8 2-thienylzinc chloride 
• 88-15-3 2-Acetylthiophene 
• 4298-52-6 2-ethynyl-thiophene 
• 874-84-0 2-(2-nitroethenyl)thiophene 
• 626-44-8 1,3,5-Triiodobenzene 
• 5713-61-1 thiophen-2-yl magnesium bromide 
• 54663-78-4 tributyl(thien-2-yl)stannane 
• 6165-68-0 thiophene boronic acid 
• 2309-48-0 1,3-di(thiophen-2-yl)propenone 
• 67-68-5 dimethyl sulfoxide 
• 193978-23-3 2-thiopheneboronic acid pinacol ester 
• 1003-09-4 2-bromothiophene 
• 365564-05-2 1,3,5-tris(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene 

Downstream Products

• 1315509-94-4 C₇₅H₇₂S₃ 
• 1315509-92-2 C₃₆H₄₅Br₃S₃ 
• 1315509-91-1 C₄₅H₆₉Br₃S₃Si₃ 
• 1315509-90-0 C₁₈H₆Br₆S₃ 
• 161299-90-7 1,3,5-tris(5-bromothiophen-2-yl)benzene 
• 1244562-44-4 C₅₄H₉₀S₃Sn₃ 
• 1273320-63-0 2-[3,5-di(thiophen-2-yl)phenyl]-9-(phenylsulfonyl)-9H-thieno-[2,3-b]carbazole 

Relevant academic research and scientific papers

Shape and size effects in the crystal structures of complexes of 1,3,5-trinitrobenzene with some trigonal donors: The benzene-thiophene exchange rule

The crystal chemistry of molecular complexes of several trigonal donor molecules with the trigonal acceptor 1,3,5-trinitrobenzene, TNB, is reported. Generally, replacement of a moiety by another of similar shape and size does not change the overall packin

Multi-color electrochromism containing green color based on electrochemically polymerized star-shaped phenyl bithiophene

A star-shaped thiophene derivative, namely PHBT, consisting of one central core of phenyl and three arms of bithiophene, was newly synthesized and characterized, in order to further investigate the relationship between the star-shaped monomer structure (c

Giant extended π-conjugated dendrimers containing the 10,15-dihydro-5H-diindeno[1,2-a;1′,2′-c]fluorene chromophore: Synthesis, NMR behaviors, optical properties, and electroluminescence

This paper reports the facile synthetic strategy of a series of novel π-conjugated dendrimers (G0 and G1) based on 10,15-dihydro-5H-diindeno [1,2-a;1′,2′-c]fluorene (truxene) in which the benzene cores are generated "in-situ" from acetyl aromatics by the

Synthesis, electrochemistry, and electrochromic properties of branched thiophene polymers with different conjugation lengths

Here we design and synthesize three branched thiophene polymers with different effective conjugation lengths of thiophene groups, pTPBT, pTPTT, and pTPQT, mainly based on bithiophene, trithiophene, and quadruple thiophene, respectively. The electrochemical curves and theoretical calculation results reflect that the oxidation potential of polymers decreased gradually as the conjugation lengths of thiophene groups increased, which is favorable to the appearance of electrochromism. Electrochromic properties demonstrate that pTBTT displays no electrochromism, pTPTT exhibits an unstable one, while pTPQT shows an obvious stable electrochromism between yellow-orange and blue-violet colors. These results indicate that thiophene polymers with effective electrochromism should be of the smallest conjugation length of quadruple thiophene at least.

The synthesis and properties of solution processable phenyl cored thiophene dendrimers

In this paper we describe the convergent synthesis of a new class of phenyl cored thiophene dendrimers, which are promising candidates for use in organic semiconductor devices. We have prepared dendrimers with three and four dendrons around the core as we

Sulfated tungstate catalyzed synthesis of C3-symmetric 1,3,5-triaryl benzenes under solvent-free condition

Sulfated tungstate catalyzed environmentally benign, simple, one pot, and solvent-free method has been developed for the synthesis of 1,3,5-triarylbenzenes via cyclic self-condensation of three molecules of aryl ketones. High yields, short reaction time, easy work-up procedure and recycling of the catalyst endorse advantage.

Synthesis and Electrochromic Properties of Star-Shaped Oligomers with Phenyl Cores

A series of star-shaped conjugated oligomers, 1,3,5-tri(2′-thienyl) benzene (3TB), 1,3,5-tri(3′,4′-ethylenedioxythienyl) benzene (3EB), 1,3,5-tri[5′,2“-(3”,4“-ethylenedioxy-thienyl)-2′-thienyl] benzene (3ETB), and 1,3,5-tri[5′,2”-(3“,4”-ethylenedioxy-thie

Phenyl-1,3,5-trithienyl-diketopyrrolopyrrole: A molecular backbone potentially affording high efficiency for solution-processed small-molecule organic solar cells through judicious molecular design

Finding new molecular backbones is necessary for further advances in solution-processed small-molecule organic solar cells (SM-OSCs). Increasing molecular π conjugation generally enhances the light-harvesting ability, and the resulting strong π-π-stacking interactions improve the charge-carrier transport ability; both increase the efficiency. In this study, we focus on the phenyl-1,3,5-trithienyl (3T-P) backbone because of its C3 symmetry, planarity, and particularly high conjugation between the three arms through the core phenyl unit. When the three arms were functionalized with diketopyrrolopyrrole (DPP) units to afford 3D-T-P, only modest efficiency was achieved (1.16 %). Introduction of 4,8-bis(2-(2-ethylhexylthienyl)) benzodithiophene (BDT) between the 3T-P and DPP units to give 3D-B-T-P enhanced the light-harvesting ability, and particularly improved the hole mobility by 1.5 orders of magnitude (5.91×10-2 versus 1.05×10 -3 cm2 V-1 s-1). When using PC71BM as the acceptor material, 3D-B-T-P gave the best power conversion efficiency (PCE) of 2.27 %, which is about 1.9 times higher than the best efficiency from 3D-T-P (≈1.16 %). The efficiency can be improved up to 3.60 % with 3 % (v/v) of 1,8-diiodooctane (DIO) as the cosolvent and thermal annealing at 100 °C for 10 min. This PCE is, to the best of our knowledge, the highest efficiency reported to date among the phenyl-1,3,5-based C3-symmetric molecules. Removing one DPP unit from 3D-T-P to form 2D-T-P, or from 3D-B-T-P to form 2D-B-T-P both decreased the light-harvesting ability and the hole mobility, thereby affording lower efficiency. Taken together, our results demonstrate that the planar phenyl-1,3,5-trithienyl-based C3-symmetric structure can be a promising backbone, and enhancing the conjugation of the 3D-T-P backbone can effectively improve the device performance.

Hydrogen-Bonding Controlled Nickel-Catalyzed Regioselective Cyclotrimerization of Terminal Alkynes

Herein we report a hydrogen-bonding controlled nickel-catalyzed regioselective cyclotrimerization of terminal alkynes in moderate to excellent yields with high regioselectivities toward 1,3,5-trisubstituted benzenes. This method features a cheap catalyst, mild reaction conditions, and excellent functional group compatibility. The Ni-B(OH)2 complex in situ generated from NiCl2·DME and tetrahydroxydiboron might act as an active catalyst. After three consecutive cis-additions of terminal alkynes, internal migratory insertion cyclization, and β-boron elimination induced aromatization, 1,3,5-trisubstituted benzenes were selectively established.

Iron-catalyzed trimerization of terminal alkynes enabled by pyrimidinediimine ligands: A regioselective method for the synthesis of 1,3,5-substituted arenes

The development of pyrimidine-based analogues of the well-known pyridinediimine (PDI) iron complexes enables access to a functional-group-tolerant methodology for the catalytic trimerization of terminal aliphatic alkynes. Remarkably, in contrast to established alkyne trimerization protocols, the 1,3,5-substituted arenes are the main reaction products. Preliminary mechanistic investigations suggest that the enhanced π-acidity of the pyrimidine ring, combined with the hemilability of the imine groups coordinated to the iron center, facilitates this transformation. The entry point in the catalytic cycle is an isolable iron dinitrogen complex. The catalytic reaction proceeds via a 1,3-substituted metallacycle, which explains the observed 1,3,5-regioselectivity. Such a metallacycle could be isolated and represents a rare 1,3-substituted ferracycle obtained through alkyne cycloaddition.