Background: Functional organic dyes with donor-π-conjugation-acceptor (D-π-A) molecular structure and electron transfer in the excited state have attracted much attention because of their potential applications in optical, electronics, magnets materials, dye sensitized solar cells (DSSCs), organic light emitting diodes (OLED), sensors, solid state lasers and photovoltaic cells and thin film transistors.

Methods: An efficient and convenient method for synthesis of 2,6-bis-[2-(4-dialkylaminophenyl) vinyl]- 4H-Pyran-4-one starting from reaction of 4-fluorobenzaldehyde with 2,6-dimethyl-4H-pyran-4- one in the presence of MeONa as base was described. In continuation, secondary amines were reacted with 2,6-bis((E)-4-fluorostyryl)-4H-pyran-4-one and 2,6-bis-[2-(4-dialkylaminophenyl)vinyl]-4HPyran- 4-one was obtained as the final product. 1H and 13C NMR, FT-IR spectroscopy supported the predicted structure of the products. The UV-Vis absorption spectra of synthesis compound were measured in diluted dichloromethane solution.

Results: Knoevenagel reaction of 4-fluorobenzaldehyde and 2,6-dimethyl-4H-pyran-4-one to afford 2,6-bis((E)-4-fluorostyryl)-4H-pyran-4-one was performed in room temperature.To optimize the reaction conditions, a variety of solvents (EtOH, MeOH, t-BuOH) and bases (KOH, NaOH, EtONa, Me- ONa, t-BuONa) were tested; MeOH/MeONa system was selected as the best condition for this step. The best operative system for nucleophilic aromatic substitution of secondary amines with 2,6-bis((E)- 4-fluorostyryl)-4H-pyran-4-one was obtained when DMF was used as a solvent and K2CO3 was employed as the base and HDTMAB as ligands. In addition, malononitrile was reacted with 2,6-bis((E)-4- fluorostyryl)-4H-pyran-4-one and obtained compound was employed in SNAr reaction. The UV-Vis spectroscopy studies were carried out in diluted dichloromethane solution (5×10-5 M) on the synthesized bis-condensed DCM derivatives.

Conclusion: In summary, this study focused on preparation of novel compounds with bis-DCM-type skeleton for application in organic light-emitting diodes, for this purpose, 2,6-bis-[2-(4-dialkylaminophenyl) vinyl]- 4H-Pyran-4-one derivatives were prepared from reaction of 4-fluorobenzaldehyde with 2,6-dimethyl- 4H-pyran-4-one in the presence of MeONa as base. In continuation, secondary amines were reacted with 2,6-bis((E)-4-fluorostyryl)-4H-pyran-4-one and 2,6-bis-[2-(4-dialkylaminophenyl) vinyl]-4HPyran- 4-one was obtained as the final product. Additionally, reaction of malononitrile as an active methylene group with 2,6-bis((E)-4-fluorostyryl)-4H-pyran-4-one before N-arylation reaction resulted in 2-(2,6-bis(4-(dialkylamino)styryl)-4H-pyran-4ylidene)malononitrile derivatives.

背景：具有供体-π-共轭受体（D-π-A）分子结构和处于激发态的电子转移的功能性有机染料因其在光学，电子，磁体材料，染料敏化太阳能电池中的潜在应用而备受关注。 （DSSC），有机发光二极管（OLED），传感器，固态激光器，光伏电池和薄膜晶体管。

方法：从4-氟苯甲醛与2,6-二甲基-4H-的反应开始，合成2,6-双-[2-（4-二烷基氨基苯基）乙烯基] -4H-吡喃-4-酮的一种有效而便捷的方法描述了以MeONa为碱存在的吡喃-4-一。继续，仲胺与2，6-双（（E）-4-氟苯乙烯基）-4H-吡喃-4-酮和2，6-双-[2-（4-二烷基氨基苯基）乙烯基] -4HPyran-反应。获得4-酮作为最终产物。1 H和13 C NMR，FT-IR光谱证实了产物的预测结构。在稀释的二氯甲烷溶液中测量合成化合物的UV-Vis吸收光谱。

结果：在室内进行了4-氟苯甲醛和2,6-二甲基-4H-吡喃-4-酮的Knoevenagel反应，得到2,6-双（（E）-4-氟苯乙烯基）-4H-吡喃-4-酮为了优化反应条件，测试了多种溶剂（EtOH，MeOH，t-BuOH）和碱（KOH，NaOH，EtONa，Me-ONa，t-BuONa）。选择MeOH / MeONa系统作为该步骤的最佳条件。当以DMF为溶剂，以K2CO3为碱时，获得了2,6-双（（E）-4-氟苯乙烯基）-4H-吡喃-4-酮对仲胺进行亲核芳族取代的最佳操作体系。和HDTMAB作为配体。另外，丙二腈与2，6-双（（E）-4-氟苯乙烯基）-4H-吡喃-4-酮反应，得到的化合物用于SNAr反应。

结论：总之，本研究集中于制备具有双DCM型骨架的新型化合物，以用于有机发光二极管，为此目的，使用了2,6-双-[2-（4-（4-二烷基氨基苯基）乙烯基]-在MeONa作为碱的存在下，由4-氟苯甲醛与2,6-二甲基-4H-吡喃-4-酮反应制得4H-吡喃-4-酮衍生物。继续，仲胺与2，6-双（（E）-4-氟苯乙烯基）-4H-吡喃-4-酮和2，6-双-[2-（4-二烷基氨基苯基）乙烯基] -4HPyran-反应。获得4-酮作为最终产物。另外，丙二腈作为活性亚甲基与2,6-双（（E）-4-氟苯乙烯基）-4H-吡喃-4-酮在N-芳基化反应之前的反应导致了2-（2,6-双（4） -（二烷基氨基）苯乙烯基）-4H-吡喃-4亚烷基）丙二腈衍生物。