Reaction of ?-pyrones with 1,3-bis(dicyanomethylene)indan

Bespalov, B. P.; Abolin, A. G.; Rumyantsev, V. G.

doi:10.1007/bf00506059

Cited by 9 publications

(7 citation statements)

References 6 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Synthesis: Chromophores 1 – 3 were prepared by the condensation of 5‐piperidinylthiophene‐2‐carbaldehyde33 or commercial 4‐(dimethylamino)benzaldehyde with 1,3‐bis(dicyanomethylidene)indane or 3‐dicyanomethylidene‐1‐thiaindane‐1,1‐dione12a according to the procedure described in ref 34. Equimolar amounts of the aldehyde and substituted indane were suspended in acetic anhydride.…”

Section: Methodsmentioning

confidence: 99%

Tuning Wavefunction Mixing in Push–Pull Molecules: From Neutral to Zwitterionic Compounds

et al. 2012

View full text Add to dashboard Cite

A new pushpull molecule, containing an (alkylamino)thiophene as electron donor and 1,3-bis(dicyanomethylidene)-2-indenylindene as electron acceptor, has been synthesized and characterized in the solid state by X-ray crystallography, in solution by UV/Vis and NMR spectroscopy and by theoretical calculations. The quinoidal zwitterionic form of this compound was underscored both in the solid state and in moderately polar solvents. Experimental and theoretical analyses were also performed on two similar pushpull molecules, selectively chosen to vary basic chemical features such as the resonance energy of the aromatic group and the steric hindrance of the attractor. Comparative analysis of the three compounds has shown that steric hindrance, resonance energy and the polarity of the environment play a significant role in stabilizing one limiting resonance form over the other. By varying these chemical variables, fine tuning of the electronic ground state of a pushpull molecule, from the neutral aromatic form to the charge-separated zwitterion, passing through a form in which the two limiting forms contribute almost equally (the cyanine limit), can be achieved

show abstract

Section: Methodsmentioning

confidence: 99%

Tuning Wavefunction Mixing in Push–Pull Molecules: From Neutral to Zwitterionic Compounds

et al. 2012

View full text Add to dashboard Cite

show abstract

“…2-(2,6-Dimethyl-4 H -pyran-4-ylidene)-1 H -indene-1,3(2 H )-dione ( 8a ), 5-(2,6-dimethyl-4 H -pyran-4-ylidene)pyrimidine-2,4,6(1 H ,3 H ,5 H )-trione ( 8b ), 5-(2,6-dimethyl-4 H -pyran-4-ylidene)-1,3-dimethylpyrimidine-2,4,6(1 H ,3 H ,5 H )-trione ( 8c ), and 5-(2,6-dimethyl-4 H -pyran-4-ylidene)-1,3-diethyl-2-thioxodihydropyrimidine-4,6(1 H ,5 H )-dione ( 8d ) were synthesized by general method II, according to known literature sources. ,− …”

Section: Experimental Sectionmentioning

confidence: 99%

HAPPY Dyes as Light Amplification Media in Thin Films

et al. 2021

View full text Add to dashboard Cite

A series of 1H amorphous tri-phenyl pyridine (HAPPY) dyes have been synthesized from luminescent triphenyl-groupcontaining 2-methyl-6-styryl-substituted-4H-pyran-4-ylidene derivatives in reactions with benzylamine and investigated for suitability as solution-processable light-emitting medium components in thin films for amplified spontaneous emission (ASE). Conversion of a 4H-pyrane ring into a 1H-pyridine fragment enables aggregation-induced emission enhancement (AIEE) behavior in the target products and slightly increases thermal stability, glass transition temperatures, and ASE efficiency with PLQY up to 15% and ASE thresholds as low as 46 μJ/ cm 2 in neat spin-cast films, although thermal and photophysical properties are mostly dominated by the incorporated electron acceptors. Continued lasing parameter efficiency parameter improvement experiments revealed that no further optimization of HAPPY dyes by doping in polymer matrixes is required as the amplified spontaneous emission thresholds were lowest in pure neat films due to the AIEE phenomenon.

show abstract

“…Yield was 10.88 g (70.7%) of brownish yellow solid with m.p. 250 • C. 10 The obtained compound (3) could be recrystallized from a huge amount of methanol, but it is pure enough to use in further reactions without recrystallization.…”

Section: Synthesis Of Red Florescent Organic Compoundmentioning

confidence: 99%

Pyranylidene indene-1,3-dione derivatives as an amorphous red electroluminescence material

et al. 2011

View full text Add to dashboard Cite

The organic light-emitting diode (OLED) has promising applications in flat-panel displays and novel light sources. Thus far, OLED structures have mostly been made by thermal evaporation in vacuum. An alternative approach is to use small molecules that form amorphous (glassy) structures from solutions. Such compounds can be used in ink-jet printing technologies and result in reduced OLED prices. We present an original red fluorescent organic compound 2-(2-(4-(bis(2-(trityloxy)ethyl)amino)styryl)-6-methyl-4H-pyran-4-ylidene)-1H-indene-1, 3(2H)-dione (ZWK1), and its derivative 2-(2,6-bis(4-(bis(2-(trityloxy)ethyl) amino)styryl)-4Hpyran-4-ylidene)-1H-indene-1,3(2H)-dione (ZWK2), where the methyl group is replaced with a 4-substituted-styryl group. This change could improve the formation of glassy structures. The thickness of the electroluminescent layer in the device is optimized to the higher power efficiency and obtains: ITO/PEDOT:PSS (40 nm)/ZWK1 (95 nm)/LiF (1 nm)/Al (100 nm), and ITO/PEDOT:PSS (40 nm)/ZWK2 (85 nm)/LiF (1 nm)/Al (100 nm). The maximum of electroluminescence (EL) spectra for the device with the ZWK1 compound is 667 nm, which corresponds to the CIE coordinates x = 0.65 and y = 0.34. The power and luminance efficiency at a luminance of 100 cd/m 2 is 0.63 lm/W and 1.78 cd/A, respectively. Adding an additional 4-substituted-styryl group to the ZWK1 molecule shifts the maximum of EL spectra to the red region (705 nm) and decreases the efficiencies by one order.

show abstract

Reaction of ?-pyrones with 1,3-bis(dicyanomethylene)indan

Cited by 9 publications

References 6 publications

Tuning Wavefunction Mixing in Push–Pull Molecules: From Neutral to Zwitterionic Compounds

Tuning Wavefunction Mixing in Push–Pull Molecules: From Neutral to Zwitterionic Compounds

HAPPY Dyes as Light Amplification Media in Thin Films

Pyranylidene indene-1,3-dione derivatives as an amorphous red electroluminescence material

Contact Info

Product

Resources

About