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9,10-DiethynylAnthracene, also known as 9,10-bis(phenylethynyl)anthracene, is a polycyclic aromatic hydrocarbon that consists of anthracene with two ethynyl groups attached at the 9 and 10 positions. This yellowish crystalline compound has a high melting point and is insoluble in water. It is valued for its high electron mobility and efficient charge transport properties.

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  • 18512-55-5 Structure
  • Basic information

    1. Product Name: 9,10-DiethynylAnthracene
    2. Synonyms: 9,10-DiethynylAnthracene
    3. CAS NO:18512-55-5
    4. Molecular Formula: C18H10
    5. Molecular Weight: 226.272
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 18512-55-5.mol
  • Chemical Properties

    1. Melting Point: 107 °C
    2. Boiling Point: 415.4±18.0 °C(Predicted)
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: 1.17±0.1 g/cm3(Predicted)
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. CAS DataBase Reference: 9,10-DiethynylAnthracene(CAS DataBase Reference)
    10. NIST Chemistry Reference: 9,10-DiethynylAnthracene(18512-55-5)
    11. EPA Substance Registry System: 9,10-DiethynylAnthracene(18512-55-5)
  • 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: 18512-55-5(Hazardous Substances Data)

18512-55-5 Usage

Uses

Used in Organic Electronic Devices:
9,10-DiethynylAnthracene is used as a component in organic light-emitting diodes (OLEDs) and field-effect transistors (OFETs) for its high electron mobility and efficient charge transport properties, which are crucial for the performance of these devices.
Used in Organic Semiconductor Synthesis:
It serves as a building block in the synthesis of organic semiconductors, which are essential for creating functional materials with a wide range of optoelectronic applications.
Used in Photovoltaic Devices:
9,10-DiethynylAnthracene is utilized in the development of photovoltaic devices due to its promising properties that can enhance the efficiency and performance of solar cells.
Used in Organic Thin-Film Transistors:
9,10-DiethynylAnthracene is also used in the fabrication of organic thin-film transistors, where its electron mobility and charge transport properties contribute to the device's overall functionality.

Check Digit Verification of cas no

The CAS Registry Mumber 18512-55-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,8,5,1 and 2 respectively; the second part has 2 digits, 5 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 18512-55:
(7*1)+(6*8)+(5*5)+(4*1)+(3*2)+(2*5)+(1*5)=105
105 % 10 = 5
So 18512-55-5 is a valid CAS Registry Number.

18512-55-5Related news

Synthesis and properties of organosilicon polymers containing 9,10-DiethynylAnthracene (cas 18512-55-5) units with highly hole-transporting properties09/05/2019

Coupling reactions of 9,10-di(lithioethynyl)anthracene with dichloromono-, di-, and trisilanes, Cl(SiR2)mCl (m=1–3) gave polymers composed of alternating 9,10-diethynylanthracene and organosilicon units. With dichlorotetraorganodisilanes, the corresponding dianthracenophanes composed of two 9,1...detailed

18512-55-5Relevant articles and documents

Anthracene derived dinuclear gold(I) diacetylide complexes: Synthesis, photophysical properties and supramolecular interactions

Mishra, Veenu,Raghuvanshi, Abhinav,Saini, Anoop Kumar,Mobin, Shaikh M.

, p. 103 - 109 (2016)

New anthracene derived dinuclear Au(I)-diacetylide complex (1) has been synthesized in which two Au(I) units are attached at 9,10- positions of ethynyl anthracene moiety. 1 exhibits rare non-covalent intermolecular Au?H-C interactions, leading to the formation of a supramolecular 2D-network. Further, to understand the effect of CCAuPPh3 units at different position, complexes (2) and (3) were synthesized, where CCAuPPh3 units are attached to 2,6- and 1,8- positions of anthracene, respectively. The absorption and emission spectra of 1-3 have been studied and surprisingly 1 was found to be highly fluorescent with high quantum yield compared to 2 and 3, this may be due to more perturbation of Au(I) on π system. Complexes 1-3 have been characterized by elemental analysis, NMR and Mass spectroscopy and authenticated by their single-crystal X-ray structures.

Polyalkynylanthracenes-syntheses, structures and their behaviour towards UV irradiation

Lamm, Jan-Hendrik,Glatthor, Johanna,Weddeling, Jan-Henrik,Mix, Andreas,Chmiel, Jasmin,Neumann, Beate,Stammler, Hans-Georg,Mitzel, Norbert W.

, p. 7355 - 7365 (2014)

A series of bis- and tris[(trimethylsilyl)ethynyl]anthracenes (1,5-, 1,8-, 9,10- and 1,8,10-) has been synthesised by multistep (cross coupling) reactions and the behaviour of the SiMe3-functionalised alkynylanthracene derivatives towards UV irradiation was qualitatively studied by NMR spectroscopy. In the case of 9,10-bis[(trimethylsilyl)ethynyl]anthracene we observed a photodimerisation upon UV irradiation; the third example was reported for a symmetrically 9,10-difunctionalised anthracene derivative, besides those with small fluorine- and methyl-substituents. The anthracene dimerisation is completely thermally reversible and the temperature dependence of the cycloelimination reaction was studied by 1H VT-NMR experiments. The (deprotected) 1,5- and 1,8-diethynylanthracenes were converted with (dimethylamino)trimethylstannane to obtain the corresponding SnMe 3-functionalised alkynes, potentially useful as highly conjugated building blocks in Stille cross coupling reactions. The new anthracene compounds were completely characterised by multinuclear NMR spectroscopy, (high resolution) mass spectrometry and-in most cases-by X-ray diffraction experiments. This journal is the Partner Organisations 2014.

Synthesis, characterization, and properties of anthracene-bridged bimetallic ruthenium vinyl complexes [rucl(co)(pme3) 3]2(μ-CH=CH-anthracene-CHdCH)

Ou, Ya-Ping,Jiang, Chuanyin,Wu,Xia, Jianlong,Yin, Jun,Jin, Shan,Yu, Guang-Ao,Liu, Sheng Hua

, p. 5763 - 5770 (2011)

Four anthracene-based bimetallic ruthenium vinyl complexes, in which two ruthenium units are attached at different positions (the 9,10-, 1,5-, 2,6-, and 1,8-positions) of the anthracene moiety, have been synthesized by treating the appropriate anthracene-based ethynes with [RuHCl(CO)-(PPh3) 3]. These bimetallic complexes have been thoroughly characterized by NMR, X-ray diffraction, and elemental analysis. According to the single-crystal X-ray structures, the 2,6-disubstituted ruthenium vinyl complex has a more planar structure compared with the 9,10-disubstituted complex, possibly because it has less steric hindrance. Furthermore, we have investigated the optical electronic properties of these complexes, such as their UV/vis absorption spectra, fluorescence spectra, and electrochemical properties. The optical electronic results indicated that the 2,6-disubstituted ruthenium vinyl complex displayed the strongest fluorescence emission due to the more planar structure of its organic conjugated bridge, and the electrochemical studies showed that the two ruthenium centers displayed obvious differences in electronic communication when they are located at different positions on the anthracene unit, with the 9,10-and 1,8-disubstituted ruthenium vinyl complexes exhibiting better electronic communication and higher stability of the mixed-valence complex than the 1,5-and 2,6-disubstituted complexes. 2011 American Chemical Society.

Aza-Diels-Alder Approach to Diquinolineanthracene and Polydiquinolineanthracene Derivatives

Dibble, David J.,Kurakake, Reina,Wardrip, Austin G.,Bartlett, Andrew,Lopez, Robert,Linares, Jose Armando,Firstman, Marcus,Schmidt, Alexander M.,Umerani, Mehran J.,Gorodetsky, Alon A.

, p. 502 - 505 (2018/02/10)

This study describes the synthesis of modular diquinolineanthracene and polydiquinolineanthracene derivatives. The reported facile and scalable aza-Diels-Alder-based approach requires mild conditions, proceeds in two steps, uses commercially available starting materials, and accommodates varying functionalities. Given the known utility of the acene and quinoline motifs, the synthesized molecules and polymers hold promise for organic electronics applications.

The relationship between molecular structure and electronic properties in dicyanovinyl substituted acceptor-donor-acceptor chromophores

Tarku?, Simge,Eelkema, Rienk,Grozema, Ferdinand C.

, p. 4994 - 5004 (2017/07/27)

In this contribution we describe a combined experimental and theoretical study of the relation between the molecular structure and the electronic properties of conjugated donor-acceptor type chromophores for light-harvesting applications. A series of model systems was synthesized where a central anthracene (electron donor) is connected to dicyanovinyl units (electron acceptor) through a π-conjugated spacer. The study of the redox and optical properties of these chromophores and of reference compounds without dicyanovinyl units allows us correlate the electronic properties to the presence of the electron withdrawing groups and the molecular conformation. Comparison with calculated electronic structure shows that the construction of chromophores that consist of electron donating and accepting units does not always follow the simple rules that are generally used in the design of such molecules. The results show a subtle relation between the charge transfer character and the geometry of the molecules. In some cases this leads to significant contribution of charge transfer excitation to the absorption spectra of some chromophores while such contributions are completely absent in others.

Cascade energy transfer and tunable emission from nanosheet hybrids: Locating acceptor molecules through chiral doping

Goudappagouda,Wakchaure, Vivek Chandrakant,Ranjeesh, Kayaramkodath Chandran,Abhai, Chalona Antony Ralph,Babu, Sukumaran Santhosh

supporting information, p. 7072 - 7075 (2017/07/10)

Light harvesting donor-acceptor assemblies are indispensable to efficiently tap photons. In an attempt to improve the light harvesting efficiency of an acceptor doped assembly, we design and synthesize a donor-acceptor-donor triad which exhibits an except

Tris(trifluoromethyl)germylethynyl derivatives of biphenyl and anthracene: Synthesis, structure, and evidence of the intramolecular charge transfer on the germanium center

Ermolaev, Nikolai L.,Lenin, Ilya V.,Fukin, Georgii K.,Shavyrin, Andrei S.,Lopatin, Mikhail A.,Kuznetsova, Olga V.,Andreev, Boris A.,Kryzhkov, Denis I.,Ignatov, Stanislav K.,Chuhmanov, Evgeny P.,Berberova, Nadezhda T.,Pashchenko, Konstantin P.

, p. 83 - 95 (2015/09/01)

Symmetrical and unsymmetrical 4,4′-biphenyl, and 9,10-anthracene derivatives with tris(trifluoromethyl)germylethynyl -CC-Ge(CF3)3 substitutes have been prepared, their properties have been studied and compared with those of dimethyl(

Synthesis and self-assembly of oligomers containing cruciform 9,10-bis(arylethynyl)anthracene unit: Formation of supramolecular nanostructures based on rod-length-dependent organization

Zhu, Jikai,Zhong, Keli,Liang, Yongri,Wang, Zhuoshi,Chen, Tie,Jin, Long Yi

, p. 1230 - 1235 (2014/02/14)

Conjugated rod-coil molecules, incorporating flexible and rigid blocks, have a strong affinity to self-organize into various supramolecular nanostructures in the bulk state.In this study, we report synthesized oligomers containing cruciform 9,10-bis(aryle

Conjugated NDI-donor polymers: Exploration of donor size and electrostatic complementarity

Alvey, Paul M.,Ono, Robert J.,Bielawski, Christopher W.,Iverson, Brent L.

, p. 718 - 726 (2013/03/29)

Conjugated donor-acceptor copolymers comprised of electron-deficient 1,4,5,8-naphthalenetetracarboxylic diimide (NDI) linked to a series of relatively electron-rich aromatics via ethynyl spacers were synthesized and characterized. While LUMO levels remained constant at -3.75 eV, HOMO levels were sensitive to the relatively electron-rich aromatic donors and systematically tuned from -5.68 to -5.17 eV. Regardless of the electron-rich comonomer, fluorescence and X-ray diffraction data were consistent with the polymer chains being assembled through the stacking of NDI moieties in an offset face-to-face fashion rather than alternating donor-acceptor stacks.

Supramolecular polymer for explosives sensing: Role of H-bonding in enhancement of sensitivity in the solid state

Gole, Bappaditya,Shanmugaraju, Sankarasekaran,Bar, Arun Kumar,Mukherjee, Partha Sarathi

, p. 10046 - 10048 (2011/10/12)

A π-electron rich supramolecular polymer as an efficient fluorescent sensor for electron deficient nitroaromatic explosives has been synthesized, and the role of H-bonding in dramatic amplification of sensitivity/fluorescence quenching efficiency in the s

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