Synthesis and Nonlinearity of Triene Chromophores Containing the Cyclohexene Ring Structure

Abstract

A series of conjugated donor−acceptor trienes in which the central double bond is incorporated into an unsaturated isophorone, verbenone, or chromone ring has been synthesized. In each case, the donor group consists of an amine and an aromatic or heterocyclic ring system, and the acceptor is the dicyanomethylidene group. The nonlinear optical properties of each of the compounds has been measured and correlated with its structure. The dipole moments and molecular hyperpolarizabilities of these compounds, like those of other conjugated polyenes, are large enough to be used as the active components of electrooptic polymers. Unlike other donor−acceptor polyenes, however, these compounds exhibit the thermal stability required for such applications.

New Organic Nonlinear Optical Polyene Crystals and Their Unusual Phase Transitions

“…To introduce the chirality of the hydroxyl group on the pyrrolidine ring of the chromophores, the enantiopure pyrrolidine derivatives such as D-3-pyrrolidinol (98 %), D-prolinol (99 %), and L-prolinol (99 %) were used. The chromophores were synthesized by two consecutive Knoevenagel condensations with the corresponding aldehydes according to the literature [15][16][17].…”

“…The chromophores were synthesized by consecutive Knoevenagel condensations according to literature procedures. [15][16][17] To introduce the chirality of the hydroxyl group on the pyrrolidine ring the enantiopure pyrrolidine derivatives such as D-3-pyrrolidinol (98 %), D-prolinol (99 %), and L-prolinol (99 %) were used for the synthesis. After the synthesis, the material used for all the experiments was purified by recrystallization from methylenechloride/methanol several times.…”

“…Other investigations have been focused on improving the thermal stability of chromophores. [13][14][15] However, there are only a few reports on the successful development of simultaneously highly nonlinear optical crystals and reliable thermal stability for melt-based crystal growth techniques.…”

Synthesis and properties of chiral helical chromophore-functionalised polybinaphthalenes for second-order nonlinear optical applications

“…6. 16a is a commercial product (disperse red 1) and 16b, 17a [11] and 17b [11] were synthesized according to literature procedures. The synthesis of chromophores 8a and 8b is schematically shown in Fig.…”

Supramolecular Ordered Organic Thin Films for Nonlinear Optical and Optoelectronic Applications

“…3) was synthesized by two consecutive Knoevenagel condensations. The intermediate was prepared by the condensation of 3,5,5-trimethyl-2-cyclohexen-1-ol with malononitrile using ammonium acetate and was then used for the second condensation with 4-dimethylaminobenzaldehyde using piperidine, according to [52]. The CLP crystals were obtained by a slow cooling technique in methanol.…”