38172-19-9Relevant academic research and scientific papers
Studies on ?-Acceptor Molecules Containing the Dicyanomethylene Group. X-Ray Crystal Structure of the Charge-transfer Complex of Tetramethyltetrathiafulvalene and 2,3-Dicyano-1,4-naphthoquinone: (TMTTF)3-(DCNQ)2
Batsanov, Andrei S.,Bryce, Martin R.,Davies, Stephen R.,Howard, Judith A. K.,Whitehead, Roger,Tanner, Brian K
, p. 313 - 319 (1993)
The reaction of tetramethyltetrathiafuvalene (TMTTF, 7) with 2-dicyanomethyleneindane-1,3-dione (DCID, 1) leads to isomerisation of DCID to 2,3-dicyanonaphthoquinone (DNCQ, 3) to yield the charge-transfer complex 2.+-(DCNQ.-)2, 8.The X-ray crystal structure of complex 8 reveals stacks of TMTTF molecules along the x direction in the sequence A..B..A..A..B..A..etc.The A..A and A..B interplanar separation distances are 3.51 Angstroem and 3.44 Angstroem, respectively.The DCNQ radical anions form dimers, with a remarkably short interplanar separation of 3.02 Angstroem, which are orthogonal to the TMTTF stacks.The complex is diamagnetic.Other ?-acceptor molecules containing the dicyanomethylene group, viz. compounds 2 and 10 -12, have been prepared and their redox properties studied by cyclic voltammetry.Compound 2 rearranges to compound 4 on complexation with TTF 6.DCID derivatives 1 and 2 react with a range of amines, by displacement of one cyano group, to yield enamines 15-19; the amphiphilic compound 18 forms Langmuir-Blodgett films which exhibit weak second harmonic generation.
Design, synthesis, and structural and spectroscopic studies of push-pull two-photon absorbing chromophores with acceptor groups of varying strength
Morales, Alma R.,Frazer, Andrew,Woodward, Adam W.,Ahn-White, Hyo-Yang,Fonari, Alexandr,Tongwa, Paul,Timofeeva, Tatiana,Belfield, Kevin D.
, p. 1014 - 1025 (2013/04/10)
A new series of unsymmetrical diphenylaminofluorene-based chromophores with various strong π-electron acceptors were synthesized and fully characterized. The systematic alteration of the structural design facilitated the investigation of effects such as molecular symmetry and strength of electron-donating and/or -withdrawing termini have on optical nonlinearity. In order to determine the electronic and geometrical properties of the novel compounds, a thorough investigation was carried out by a combination of linear and nonlinear spectroscopic techniques, single-crystal X-ray diffraction, and quantum chemical calculations. Finally, on the basis of two-photon absorption (2PA) cross sections, the general trend for π-electron accepting ability, i.e., ability to accept charge transfer from diphenylamine was: 2-pyran-4-ylidene malononitrile (pyranone) > dicyanovinyl > bis(dicyanomethylidene)indane >1-(thiophen-2-yl)propenone > dicyanoethylenyl >3-(thiophen-2-yl)propenone. An analogue with the 2-pyran-4-ylidene malononitrile acceptor group exhibited a nearly 3-fold enhancement of the 2PA cross section (1650 GM at 840 nm), relative to other members of the series.
Synthetic and mechanistic studies of metal-free transfer hydrogenations applying polarized olefins as hydrogen acceptors and amine borane adducts as hydrogen donors
Yang, Xianghua,Fox, Thomas,Berke, Heinz
experimental part, p. 852 - 860 (2012/02/05)
Metal-free transfer hydrogenation of polarized olefins (RR′ CCEE′: R, R′ = H or organyl, E, E′ = CN or CO2Me) using amine borane adducts RR′NH-BH3 (R = R′ = H, AB; R = Me, R′ = H, MAB; R = tBu, R′ = H, tBAB; R = R′ = Me, DMAB) as hydrogen donors, were studied by means of in situ NMR spectroscopy. Deuterium kinetic isotope effects and the traced hydroboration intermediate revealed that the double H transfer process occurred regio-specifically in two steps with hydride before proton transfer characteristics. Studies on substituent effects and Hammett correlation indicated that the rate determining step of the HN transfer is in agreement with a concerted transition state. The very reactive intermediate [NH2BH2] generated from AB was trapped by addition of cyclohexene into the reaction mixture forming Cy2BNH2. The final product borazine (BHNH)3 is assumed to be formed by dehydrocoupling of [NH2BH2] or its solvent stabilized derivative [NH2BH2]-(solvent), rather than by dehydrogenation of cyclotriborazane (BH2NH 2)3 which is the trimerization product of [NH 2BH2].
Naphthyl derivatives functionalised with electron acceptor units - Synthesis, electronic characterisation and DFT calculations
Planells, Miquel,Robertson, Neil
, p. 4947 - 4953,7 (2020/08/24)
A series of unsymmetrical dyes containing a naphthyl unit connected to an electron acceptor moiety was designed and synthesised. By modifying the electron acceptor unit, a shift of the LUMO energy level as well as its distribution through the molecule were achieved. These dyes were fully characterised by optical, computational and electrochemical techniques. In addition, crystal structures reveal different packing depending upon the nature of the acceptor. Their potential use as electron acceptor materials for organic photovoltaics (OPVs) was also investigated by photoluminescence studies of blends with the common OPV polymers P3HT and PCDTBT. A series of unsymmetrical dyes was synthesised and characterised. Their optical and electrochemical properties were tuned by modifying the electron acceptor unit. Copyright
Efficient near infrared D-π-A sensitizers with lateral anchoring group for dye-sensitized solar cells
Hao, Yan,Yang, Xichuan,Cong, Jiayan,Tian, Haining,Hagfeldt, Anders,Sun, Licheng
supporting information; scheme or table, p. 4031 - 4033 (2009/12/09)
A new strategy in which the anchoring group is separated from the acceptor groups of the dyes was developed; among these dyes, the HY103 dye gives a maximum IPCE value of 86% at 660 nm and an η value of 3.7% in the NIR region reported in DSCs.
A new type of cation responsive chromoionophore with spectral sensitivity in the near-infrared spectral range
Citterio, Daniel,Sasaki, Shin-ichi,Suzuki, Koji
, p. 552 - 553 (2007/10/03)
A long wavelength absorbing cation responsive chromoionophore 1 based on the strongly π-electron accepting dicyanovinylindane subunit and an electron donating N-phenylazacrown ether binding site was synthesized. The absorption spectra of this compound in
New conjugated systems with multiple redox states
Raimundo,Akoudad,Brisset,Roncali
, p. 1234 - 1237 (2007/10/03)
New linear π-conjugated systems based on the association of thiophene- based donors and an acceptor group derived from indan-l,3-dione have been synthesized. Electrochemical and optical data are consistent with a small HOMO-LUMO gap and strong electron-acceptor properties.
Near-infrared Absorbing Methine Dyes based on Dicyanovinyl Derivatives of Indane-1,3-dione
Bello, Kasali A.,Cheng, Lubai,Griffiths, John
, p. 815 - 818 (2007/10/02)
The synthesis, colour, and constitution of methine dyes formed by condensation of benzaldehydes and nitrosobenzenes with dicyanovinyl analogues of indane-1,3-dione have been investigated. 3-Dicyanovinylindan-1-one (3) and 1,3-bisdicyanovinylindane (5) giv
POLYMETHINE DYES WITH HYDROCARBON BRIDGES. ANIONIC DYES WITH AN o-PHENYLENE GROUP IN THE CHROMOPHORE
Slominskii, Yu. L.,Popov, S. V.,Dyadyusha, G. G.,Kachkovskii, A. D.,Tolmachev, A. I.
, p. 1786 - 1793 (2007/10/02)
Pentamethine and heptamethine dyes containing an o-phenylene bridge in the chromophore were obtained on the basis of malononitrile.It was shown that cyclization of the part of the polymethine chain by the o-phenylene group leads a bathochromic or hypsochr
