81090-53-1

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Uses

Polytriarylamine Semiconductors

InChI:InChI=1/C18H13Br2N/c19-14-6-10-17(11-7-14)21(16-4-2-1-3-5-16)18-12-8-15(20)9-13-18/h1-13H

Upstream product

• 16292-17-4 bis(4-bromophenyl)amine 
• 637-88-7 1,4-Cyclohexanedione 
• 603-34-9 N,N-diphenylaminobenzene 
• 66-71-7 1,10-Phenanthroline 
• 591-50-4 iodobenzene 
• 4051-56-3 N,N-diphenylbenzamide 
• 104-15-4 toluene-4-sulfonic acid 
• 589-87-7 1,4-bromoiodobenzene 
• 62-53-3 aniline 
• 603-35-0 triphenylphosphine 
• 99234-92-1 N,N-bis-(4-bromophenyl)benzamide 

Downstream Products

• 25069-38-9 N,N-bis(4-bromophenyl)aminobenzaldehyde 
• 845640-45-1 N,N-bis[4-(6'-bromohexyl)phenyl]phenylamine 
• 862553-94-4 triphenylamine-4,4'-bisboronic acid 
• 1228702-13-3 5-(4-((4-bromophenyl)(phenyl)amino)phenyl)thiophene-2-carbaldehyde 
• 113664-28-1 4-cyano-4′,4′′-dibromotriphenylamine 
• 1260178-92-4 C₃₄H₂₃NO₄ 

Relevant academic research and scientific papers

Molecular Engineering of Potent Sensitizers for Very Efficient Light Harvesting in Thin-Film Solid-State Dye-Sensitized Solar Cells

Dye-sensitized solar cells (DSSCs) have shown significant potential for indoor and building-integrated photovoltaic applications. Herein we present three new D-A-A organic sensitizers, XY1, XY2, and XY3, that exhibit high molar extinction coefficients and a broad absorption range. Molecular modifications of these dyes, featuring a benzothiadiazole (BTZ) auxiliary acceptor, were achieved by introducing a thiophene heterocycle as well as by shifting the position of BTZ on the conjugated bridge. The ensuing high molar absorption coefficients enabled the fabrication of highly efficient thin-film solid-state DSSCs with only 1.3 μm mesoporous TiO2 layer. XY2 with a molar extinction coefficient of 6.66 × 104 M-1 cm-1 at 578 nm led to the best photovoltaic performance of 7.51%.

Butterfly-Like Triarylamines with High Hole Mobility and On/Off Ratio in Bottom-Gated OFETs

Highly π-extended butterfly-shaped triarylamine dyads with aryleneethynylene spacer were constructed using an efficient synthetic route. These aryleneethynylene-bridged dyads are highly fluorescent and exhibited high HOMO levels, and low bandgaps, which a

Organic small molecule hole injection/transport material and preparation method and application thereof

The invention belongs to the technical field of organic small molecule hole injection/transport materials, and discloses an organic small molecule hole injection/transport material and a preparation method and application thereof. A structural formula of the organic small molecule hole injecting/transporting material is as shown in the specification, wherein Ar1, Ar2 and Ar3 are independently unsubstituted benzene ring, fused ring or spiro ring aromatic hydrocarbons, or independently benzene ring, fused ring or spiro ring aromatic hydrocarbons substituted by an alkyl group, an alkoxy group oran alkylthio group with a carbon atom number of 1-6 respectively, and a carbon atom number of the benzene ring, fused ring or spiro ring aromatic hydrocarbons is 6-40. A plurality of non-planar structure arylamine units are adopted, and methoxy end groups are introduced, so that the material has high thermal stability, high glass transition temperature, high HOMO energy level, high hole mobility and good solubility, and has important application prospects in optoelectronic devices.

Halogen-substituted triphenylamine derivatives with intense mechanoluminescence properties

Three triphenylamine (TPA) derivatives, constructed by the introduction of halogen atoms in TPA, show strong mechanoluminescence emissions, partially due to their various electronic configurations by virtue of the electron withdrawing ability of halogen atoms. Careful investigation of their single crystals and the density functional theory (DFT) calculations based on the crystal structure demonstrate that the enhanced intermolecular interactions and the twisted molecular structure contribute to their strong ML emission.

Positive charge-dependent cell targeted staining and DNA detection

The chemical structures or positive charge-guided specific cell organelles' staining was an interesting but very challenging research work. In this paper, we synthesized a series of triphenylamine (TPA) derivatives with mono-, di- and tri-pyridinium as su

Thiophene insertion for continuous modulation of the photoelectronic properties of triphenylamine-based metal-organic frameworks for photocatalytic sulfonylation-cyclisation of activated alkenes

Pharmaceutically meaningful conversions like photocatalytic sulfonylation call for the precise control of the photoelectronic properties of photocatalysts. A ligand engineering strategy of inserting different numbers of thiophenes into the scaffold of triphenylamine (TPA)-based ligands was developed to improve the visible light absorption, enhance the oxidation potentials of the ground states, and decrease the reduction potentials of the excited states, providing a powerful tool for continuous modulation of the photoelectronic properties of metal-organic framework (MOF)-based heterogeneous photocatalysts. The ligand inserted with two thiophenes was found to possess a well-balanced photoelectronic performance, endowing the corresponding MOF Zn-BCTA with good visible light-harvesting ability and a moderate excited-state reduction potential with minimal over-potential for the photoinduced generation of sulfonyl radicals while avoiding the competitive over-reduction of the sulfonyl moieties. The breaking of the C3-symmetry of the TPA-based ligand forged a distorted coordination geometry of the Zn4O nodes of the MOF to provide potential active sites to facilitate the fixation and activation of α,β-unsaturated carbonyl substrates, and the two-fold interpenetrated frameworks further enhanced the spatial proximity between the encapsulated substrate and the photoredox-active centre. The synergy of the well-tuned photoelectronic properties of Zn-BCTA and the spatial confinement effect within the pores benefited the tandem sulfonylation-cyclisation of unsaturated alkenes in an efficient and diastereoselective mode for the construction of bio-interesting sulphoyl isoquinolinediones/oxindoles.

Pyran-annulated perylene diimide derivatives as non-fullerene acceptors for high performance organic solar cells

There has been growing interest in the effectual strategy of constructing non-fullerene acceptors for organic solar cells that may overcome the defect of traditional fullerene-based acceptors. Herein, two novel push-pull (acceptor-donor-acceptor) type sma

Photo-irradiated: E / Z isomerization reaction of star-shaped isomers containing two cyanostilbene arms with charge transfer excited states

The E/Z isomerization reaction of the multi-cyanostilbene molecule is still not clear. Herein, we have designed and synthesized three star-shaped molecular isomers with a triphenylamine core linked to two cyanostilbene groups with E/Z isomerization, Z,Z-TPDCF, Z,E-TPDCF and E,E-TPDCF, possessing three different isomeric molecular configurations, to investigate the specific E/Z isomerization reaction of the cyanostilbene groups in the two molecular arms. The in situ UV, 1H NMR and HPLC spectra under UV-irradiation clearly showed that the E/Z isomerization reactions of both E,E-TPDCF and Z,Z-TPDCF firstly turned them into Z,E-TPDCF, and the Z,E-TPDCF was almost simultaneously turned into more E,E-TPDCF and less Z,Z-TPDCF due to the calculated lowest unoccupied molecular orbitals of Z,E-TPDCF on the cyanostilbene arm with the Z-configuration. In general, Z,E-TPDCF exhibited a relatively better configurational stability than Z,Z-TPDCF or E,E-TPDCF under the photo-irradiation conditions. Further research demonstrated that all three isomers exhibited excellent aggregation-induced emission (AIE) properties.

Synthesis and Exciton Dynamics of Donor-Orthogonal Acceptor Conjugated Polymers: Reducing the Singlet-Triplet Energy Gap

The presence of energetically low-lying triplet states is a hallmark of organic semiconductors. Even though they present a wealth of interesting photophysical properties, these optically dark states significantly limit optoelectronic device performance. Recent advances in emissive charge-transfer molecules have pioneered routes to reduce the energy gap between triplets and "bright" singlets, allowing thermal population exchange between them and eliminating a significant loss channel in devices. In conjugated polymers, this gap has proved resistant to modification. Here, we introduce a general approach to reduce the singlet-triplet energy gap in fully conjugated polymers, using a donor-orthogonal acceptor motif to spatially separate electron and hole wave functions. This new generation of conjugated polymers allows for a greatly reduced exchange energy, enhancing triplet formation and enabling thermally activated delayed fluorescence. We find that the mechanisms of both processes are driven by excited-state mixing between π-πand charge-transfer states, affording new insight into reverse intersystem crossing.

Aggregation-induced emission (AIE)-active fluorescent probes with multiple binding sites toward ATP sensing and live cell imaging

Aggregation-induced emission (AIE)-active compounds are attractive fluorescent materials for applications in chemical and biological sensing. The AIE effect of such materials amplifies changes in the fluorescence signal due to the physical state transformation from aggregation to disaggregation, which can be employed for detecting various analytes with high sensitivity. In particular, specific bio-active analyte recognition is not only very interesting but also challenging. In this paper, we report a set of novel AIE-active fluorescent probes containing pyridiniums and boric acid groups (TPA-PP, TPA-PPA-1, TPA-PPA-2, TPA-PPA-3), which has been developed for adenosine 5′-triphosphate (ATP) recognition. These probes with two types of interaction modes and multiple connection sites toward ATP molecules are able to selectively discriminate ATP among other bioactive anions with a significant enhancement in fluorescence emission. In particular, in the application of cell imaging, as the number of positive charges and boric acid group increased further, the probes could penetrate into cells, and then enter into the nucleus very specifically. These results clearly demonstrate that the newly developed sensors are suitable for specific tracing of different cell organelles with a height visualization and retention ability. Therefore, all of them are confirmed as promising alternatives for live cell imaging in the future.