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