34200-53-8Relevant academic research and scientific papers
2-(p-diethylaminobenzylidene)-1,3-indandione
Khodorkovsky, Vladimir,Mazor, Royi A.,Ellern, Arkady
, p. 2878 - 2880 (1996)
The title compound, C20H19NO2, belongs to the class of donor-acceptor-substituted conjugated polyenes. Within the structure, O atoms are situated in the plane of the 1,3-indandione fragment and the N atom lies in the plane of the p-benzylidene fragment which forms a dihedral angle of 7.6 (2)° with the indandione nucleus.
Arylmethylene-1,3-indandione based molecular glasses: Third order optical non-linearity
Seniutinas,Toma?iunas,Czaplicki,Sahraoui,Da?kevi?iene,Getautis,Balevi?ius
experimental part, p. 33 - 40 (2012/07/14)
The synthesis and new optical features of three indan-1,3-dione class structures is reported. The simple arylmethylene-1,3-indandione structure 2-(4-diethylaminobenzylidene)indan-1,3-dione was used to design two linked structures: 1,3-bis-{3-hydroxy-4-[4-diethylamino-1-(1,3-dioxoindan-2- ylmethylene)benzen-3-yloxy]-1-thiabuthyl}benzene and 4,4′-bis-{{3-hydroxy- 4-[4-diethylamino-1-(1,3-dioxoindan-2-ylmethylene)benzen-3-yloxy]-1-thiabutyl} phenyl}sulfide. In contrast to the simple compound, which readily crystallized, the linked derivatives remained in an amorphous phase and are considered as molecular glasses with respective glass transition temperatures 88 and 100°C. For non-linear optical investigations samples were prepared as a guest-host system in polycarbonate matrix (10%). The Maker-fringe technique was used to investigate the third harmonic generation at a wavelength of 355 nm (YAG laser). Third-order non-linear susceptibility χ(3) values were extracted 5.75·10-21 m2 V-2, 8.60·10-21 m2 V-2, 16.85·10 -21 m2 V-2 for these respective indandiones while modeling the experimental results. To evaluate the susceptibility of the indan-1,3-dione derivatives third harmonic generation a comparative experiment for a reference azodye in polycarbonate was performed. The results show an important feature - higher molecular second order hyperpolarizability for the linked structures. NMR, MS, IR, UV-VIS, XRD and elemental analysis were used to structurally characterize the new compounds and ellipsometry was applied to interpret the non-linear optical results.
Synthesis, electronic, and electro-optical properties of emissive solvatochromic phenothiazinyl merocyanine dyes
Hauck, Martina,Stolte, Matthias,Schoenhaber, Jan,Kuball, Hans-Georg,Mueller, Thomas J. J.
experimental part, p. 9984 - 9998 (2011/10/13)
Phenothiazinyl merocyanine dyes with variable substitution patterns on the peripheral benzene ring were synthesized in good yields by Knoevenagel condensation of the corresponding phenothiazinyl aldehydes and N-methylrhodanine or indan-1,3-dione. The electronic properties were investigated by cyclic voltammetry, absorption, electro-optical absorption, and emission spectroscopy. All these merocyanines reveal reversible redox behavior that stems from the phenothiazinyl-centered oxidation to give stable radical cations. The redox potentials strongly correlate with Hammett σp parameters. All merocyanines reveal large Stokes shifts. They also display a pronounced emissive solvatochromism, which is caused by large dipole moment changes upon excitation from the ground to the excited state. These findings are supported by solvatochromism studies and time-dependent DFT computations. A dye-ing breed: Phenothiazinyl-merocyanine dyes with variable substitution patterns on the peripheral benzene ring were synthesized in good yields by Knoevenagel condensation of the corresponding phenothiazinyl aldehydes and N-methylrhodanine or indan-1,3-dione. Their electronic properties were investigated by various methods (see figure). Copyright
New Aspects in the Reaction of Azomethines with Cyclic CH-Acidic Compounds
Hennig, Lothar,Alva-Astudillo, Mario,Mann, Gerhard,Kappe, Thomas
, p. 571 - 580 (2007/10/02)
Treatment of substituted benzylidene anilines 1a - f with cyclic CH-acidic compounds 2a - m in ethanol at room temperature yields in addition/elimination reactions the corresponding arylidene derivatives 4 and the 2:1 adducts 5.The addition products 3, which are formed as intermediates, could not be isolated in any case.The donor/acceptor effect of the substituents on the benzylidene moiety influences to a significant extent the reactivity towards the azomethine carbon. Keywords.Azomethine; CH-Acidic compound; Addition/elimination reaction.
