Nonlinear optical co-crystal of analogous polyene chromophores with tailored physical properties.

Search for new potential NLO crystalline materials: Chiral derivatives of (2S)-2-(methoxymethyl)pyrrolidine

Synthesis and crystallization of a polar organic compound (2E)-2-cyano-3-[4-(diethylamino)phenyl]prop-2-enethioamide (CDPE) gave two new crystalline polymorphs (1 and 2) and an acetonitrile solvate (pseudopolymorph, 3) of this compound. The third crystalline polymorph of CDPE (4) was described in the literature earlier. It was found that in crystalline polymorphs 1, 2, and 4 molecules adopt three different conformations. Experimental observations show that polymorph 1 is a predominant form of the CDPE compound, while all other crystalline forms we were unable to reproduce under different conditions. Quantum ab initio calculations of relative conformational energies of molecules found in these polymorphs revealed that the conformer in polymorph 1 has significantly lower energy than conformers in polymorphs 2 and 4. This fact explains the predominant formation of polymorph 1 under different experimental conditions. The polarity of CDPE molecules and distinctions in their molecular and crystal structures mak...

Vanishing Polymorphism of (2E)-2-Cyano-3-[4-(Diethylamino)phenyl]prop-2-enethioamide: X-ray Structural Study and Polymorph Prediction

A quick and simple method has been developed for the synthesis of 2-amino maleonitrile Schiff bases 3(a–k) through the reaction of 2,3-diaminomaleonitrile (DAMN) and aromatic aldehydes in the presence of catalytic amounts of cerium(IV) ammonium nitrate (CAN) in aqueous media at room temperature. Also, the facile synthesis of 2-aryl-4,5-dicarbonitrile imidazoles 4(a–k) by one-pot condensation of DAMN with various aromatic aldehydes using CAN as efficient reagent in acetonitrile at 50 °C has been described. In this way, the one-pot synthesis of raw materials is presented for the first time. The new synthesized compounds were characterized using IR, 1H NMR, 13C NMR and mass spectroscopy. The present procedure offers several advantages, such as good to excellent yields, the use of an inexpensive and available catalyst, easy and quick isolation of the pure product and short reaction times compared with previous reports.

Rapid synthesis of 2-amino maleonitrile Schiff bases in aqueous media catalyzed by cerium(IV) ammonium nitrate (CAN) and a new method for the one-pot preparation of their dicyano imidazoles (DCI)

Vanillin-derived phosphorus-containing aromatic imine for flame-retardant polyurethane coating

In the course of a search for new thermostable acentric nonlinear optical crystalline materials, several heterocyclic imine derivatives were designed, with the general structure D-pi-A(D'). Introduction of a donor amino group (D') into the acceptor moiety was expected to bring H-bonds into their crystal structures, and so to elevate their melting points and assist in an acentric molecular packing. Six heterocycle-containing compounds of this type were prepared, single crystals were grown for five of them, and these crystals were characterized by X-ray analysis. A significant melting temperature elevation was found for all of the synthesized compounds. Three of the compounds were also found to crystallize in acentric space groups. One of the acentric compounds is built as a three-dimensional H-bonded molecular network. In the other two compounds, with very similar molecular structure, the molecules form one-dimensional H-bonded head-to-head associates (chains). These chains are parallel in two different crystallographic directions and form very unusual interpenetrating chain patterns in an acentric crystal. Two of the compounds crystallized with centrosymmetric molecular packing.

Thermally stable heterocyclic imines as new potential nonlinear optical materials

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Thermally stable heterocyclic imines as new potential nonlinear optical materials