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2‐(4‐Bromophenyl)‐2‐cyano‐1,1‐diphenylethylene (Br-TPAN) is a key intermediate used in the synthesis of aggregation-induced emission (AIE)-active compounds like BP2TPAN, which exhibit high thermal stability, mechanochromism, and efficient solid-state emission for low color temperature OLED applications. Its structural framework contributes to the AIE properties and thermal robustness observed in derived materials. **Returned paragraph:** 2‐(4‐Bromophenyl)‐2‐cyano‐1,1‐diphenylethylene (Br-TPAN) serves as a precursor for AIE-active materials, enabling the development of thermally stable, mechanochromic, and highly emissive compounds for optoelectronic applications such as OLEDs. Its integration into larger molecular systems enhances solid-state luminescence and stimuli-responsive behavior.

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  • 288105-06-6 Structure
  • Basic information

    1. Product Name: 2‐(4‐bromophenyl)‐2‐cyano‐1,1‐diphenylethylene
    2. Synonyms: 2‐(4‐bromophenyl)‐2‐cyano‐1,1‐diphenylethylene
    3. CAS NO:288105-06-6
    4. Molecular Formula:
    5. Molecular Weight: 360.253
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 288105-06-6.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: N/A
    3. Flash Point: N/A
    4. Appearance: N/A
    5. Density: N/A
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. CAS DataBase Reference: 2‐(4‐bromophenyl)‐2‐cyano‐1,1‐diphenylethylene(CAS DataBase Reference)
    10. NIST Chemistry Reference: 2‐(4‐bromophenyl)‐2‐cyano‐1,1‐diphenylethylene(288105-06-6)
    11. EPA Substance Registry System: 2‐(4‐bromophenyl)‐2‐cyano‐1,1‐diphenylethylene(288105-06-6)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 288105-06-6(Hazardous Substances Data)

288105-06-6 Usage

Organic compound

Belongs to the family of stilbenes and phenyl compounds
This chemical is an organic compound, which means it is primarily composed of carbon, hydrogen, and other elements such as bromine and nitrogen in this case.

Central ethylene moiety

Flanked by two phenyl rings
The core structure of the compound consists of an ethylene group (a carbon-carbon double bond) with two phenyl rings (a six-membered aromatic ring with hydrogen atoms) attached to each carbon atom of the double bond.

Cyano group

Attached to the central ethylene moiety
A cyano group (C≡N), which is a carbon-nitrogen triple bond, is present in the compound and attached to one of the carbon atoms in the central ethylene moiety.

Bromine substituent

Attached to one of the phenyl rings
A bromine atom (Br) is attached to one of the carbon atoms in one of the phenyl rings, making it a substituent on the phenyl ring.

Building block in synthesis

Used in the synthesis of various organic compounds
Stilbene serves as a starting material or building block for the synthesis of a wide range of other organic compounds, such as dyes, fluorescent brighteners, optical brighteners, and pharmaceuticals.

Unique structure and chemical reactivity

Valuable in organic chemistry
The compound's distinctive structure and its ability to undergo various chemical reactions make it an important and versatile compound in the field of organic chemistry.

Check Digit Verification of cas no

The CAS Registry Mumber 288105-06-6 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 2,8,8,1,0 and 5 respectively; the second part has 2 digits, 0 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 288105-06:
(8*2)+(7*8)+(6*8)+(5*1)+(4*0)+(3*5)+(2*0)+(1*6)=146
146 % 10 = 6
So 288105-06-6 is a valid CAS Registry Number.

288105-06-6Relevant articles and documents

A Molecular Chameleon for Mapping Subcellular Polarity in an Unfolded Proteome Environment

Chen, Weisan,Deng, Jieru,Heras, Bego?a,Hinde, Elizabeth,Hong, Yuning,Owyong, Tze Cin,Paxman, Jason J.,Subedi, Pramod,White, Jonathan M.,Wong, Wallace W. H.

, p. 10129 - 10135 (2020)

Environmental polarity is an important factor that drives biomolecular interactions to regulate cell function. Herein, a general method of using the fluorogenic probe NTPAN-MI is reported to quantify the subcellular polarity change in response to protein

A novel triphenylacrylonitrile based AIEgen for high contrast mechanchromism and bicolor electroluminescence

Hu, Jiayou,Jiang, Bingli,Gong, Yongyang,Liu, Yuanli,He, Gang,Yuan, Wang Zhang,Wei, Chun

, p. 710 - 716 (2018)

A novel thermally stable and aggregation-induced emission (AIE) active compound, 2,2'-(([1,1′-biphenyl]-4,4′-diylbis(phenylazanediyl))bis(4,1-phenylene))bis(3,3-diphenylacrylonitrile) (BP2TPAN) was synthesized through a C-N coupling reaction between 2-(4-bromophenyl)-3,3-diphenylacrylonitrile (Br-TPAN) and N,N′-diphenyl-1,4-phenylenediamine, under mild conditions using Pd(OAc)2 and P(t-Bu)3 as a catalyst. The BP2TPAN was characterized by nuclear magnetic resonance spectroscopy, high resolution mass spectrometry and elemental analysis. The thermal analysis showed that the glass transition and decomposition temperatures (5% weight loss) are 96 and 414 °C, respectively. The fluorescent emission peaks changes at 540 and 580 nm upon grinding were attributed to a transformation from crystal to amorphous occurring by altering the condensed state. The photoluminescence quantum yield and fluorescence lifetime of the as prepared and ground samples were 74.3 and 8.4%, 3.4 and 5.1 ns, respectively. The difference of the luminous efficiency of before and after grinding samples indicates BP2TPAN has a high contrast more importantly, both doped and nondoped OLED devices emit different color, the doped one is highly efficient and its Lmax, CEmax, PEmax and EQE are up to 15070 cd m-2, 11.0 cd A-1, 7.5 lm W-1, and 3.1%, respectively.

Exploration of Highly Efficient Blue-Violet Light Conversion Agents for an Agricultural Film Based on Structure Optimization of Triphenylacrylonitrile

Wang, Yongtao,Yu, Yongjiang,Liu, Wenjing,Ren, Litong,Ge, Guixian

, p. 13295 - 13302 (2019/01/03)

To obtain highly efficient blue-violet light conversion agents used for an agricultural film, six triarylacrylonitrile derivatives and their doping films were prepared. Further, the luminogens have the ability to convert ultraviolet light into blue-violet

Piezofluorochromism of triphenylamine-based triphenylacrylonitrile derivative with intramolecular charge transfer and aggregation-induced emission characteristics

Wang, Xin,Wang, Yunhan,Zhan, Yong,Yang, Peng,Zhang, Xiaojing,Xu, Yongnan

supporting information, p. 2057 - 2061 (2018/04/25)

New triphenylacrylonitrile derivative (DPPA) with triphenylamine moiety as electron donor group has been synthesized. Its emission wavelengths were strongly affected by solvent polarity, indicating intramolecular charge transfer (ICT) transitions. It was found that DPPA was almost non-emissive in tetrahydrofuran (THF), and the emission could be intensified obviously when a great amount of H2O was added, illustrating aggregation induced emission property. It is interesting that the pristine crystal of DPPA emitted green light, and the ground made its emitting color to change into orange, which could be recovered under fumed with dichloromethane (DCM) vapor. The piezofluorochromic behavior might be switched reversibly under the stimulus of external force because of crystalline-amorphous phase transformation, which could be confirmed from the results of PXRD patterns and DSC curves in different solid states. This work might open a new strategy to provide a broad perspective for the development of AIE PFC materials.

Polycarbazoles and polytriphenylamines showing aggregation-induced emission (AIE) and intramolecular charge transfer (ICT) behavior for the optical detection of nitroaromatic compounds

Dong, Wenyue,Pina, J?ao,Pan, Yuyu,Preis, Eduard,Seixas De Melo, J. Sérgio,Scherf, Ullrich

, p. 173 - 181 (2015/09/21)

Acceptor-substituted polycarbazoles (PCzTPAN) and polytriphenylamines (PTPATPAN) bearing electron-deficient 2,3,3-triphenylacrylonitrile (TPAN) side groups have been successfully synthesized. Both of them are aggregation-induced emission (AIE)-active and show intramolecular charge transfer (ICT) behavior. PCzTPAN and PTPATPAN aggregates in 90% water/THF were used for the detection of 1,3,5-trinitrobenzene (TNB) as prototypical nitroaromatic compound. They show amplified PL quenching upon addition of TNB with a maximum quenching constant of 5.5 × 105 M-1. As additional application example, the detection of the glass transition temperature of polystyrene (PS) was accomplished for PTPATPAN blended into PS at doping concentrations of 0.1-1.0 wt%.

Meso Alkynylated Tetraphenylethylene (TPE) and 2,3,3-Triphenylacrylonitrile (TPAN) Substituted BODIPYs

Dhokale, Bhausaheb,Jadhav, Thaksen,Mobin, Shaikh M.,Misra, Rajneesh

supporting information, p. 8018 - 8025 (2015/09/02)

The tetraphenylethylene (TPE) substituted BODIPY 2a, and 2,3,3-triphenylacrylonitrile (TPAN) substituted BODIPYs 2b and 2c were designed and synthesized by the Pd-catalyzed Sonogashira cross-coupling reaction. Their photophysical and electrochemical prope

AIE-active, highly thermally and morphologically stable, mechanochromic and efficient solid emitters for low color temperature OLEDs

Gong, Yongyang,Liu, Jun,Zhang, Yiren,He, Gufeng,Lu, Yang,Fan, Wen Bin,Yuan, Wang Zhang,Sun, Jing Zhi,Zhang, Yongming

, p. 7552 - 7560 (2014/12/10)

Low color temperature (CT) lighting sources such as candle light are of significant importance to human health owing to their remarkably low suppression effect on the secretion of melatonin, which helps people relax. As an alternative to hydrocarbon-burni

Twisted D-π-A solid emitters: Efficient emission and high contrast mechanochromism

Gong, Yongyang,Tan, Yeqiang,Liu, Jun,Lu, Ping,Feng, Cunfang,Yuan, Wang Zhang,Lu, Yawei,Sun, Jing Zhi,He, Gufeng,Zhang, Yongming

, p. 4009 - 4011 (2013/07/25)

Triphenylacrylonitrile and diarylamine based D-π-A luminogens exhibit typical AIE characteristics with high solid state efficiency up to unity and switchable mechanochromism with high contrast, which render them multifunctional materials for versatile applications in optical storage, volatile organic compound (VOC) detection, OLEDs, etc.

Synergy between twisted conformation and effective intermolecular interactions: Strategy for efficient mechanochromic luminogens with high contrast

Yuan, Wang Zhang,Tan, Yeqiang,Gong, Yongyang,Lu, Ping,Lam, Jacky W. Y.,Shen, Xiao Yuan,Feng, Cunfang,Sung, Herman H-Y.,Lu, Yawei,Williams, Ian D.,Sun, Jing Zhi,Zhang, Yongming,Tang, Ben Zhong

, p. 2837 - 2843 (2013/07/28)

A strategy towards efficient mechanochromic luminogens with high contrast is developed. The twisted propeller-like conformations and effective intermolecular interactions not only endow the luminogens with AIE characteristics and high efficiency in the crystalline state, but also render them to undergo conformational planarization and disruption in intermolecular interactions upon mechanical stimuli, resulting in remarkable changes in emission wavelength and efficiency. Copyright

Soluble tetrahedral compounds for use in electroluminescent devices

-

, (2008/06/13)

Electroluminescent compounds, devices and methods for making the foregoing are disclosed, which employ a novel topological strategy for designing amorphous molecular solids suitable for forming thin films in optoelectronic devices. In this approach chromophores are attached to a tetrahdral point of convergence.

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