Synthesis of Chromophores with Extremely High Electro-optic Activities. 2. Isophorone- and Combined Isophorone−Thiophene-Based Chromophores

Abstract

Four new isophorone and combined isophorone and thiophene bridged chromophores have been synthesized. All of these new high µβ chromophores possess our newly synthesized tricyanovinyldihydrofuran acceptors. Because of our unique acceptor design, all of our chromophores show high solubility in all organic solvents due to minimized chromophorechromophore electrostatic interactions. These chromophores have also been studied with respect to their solvatochromism and thermal behavior by TGA in air. Preliminary EO characterization of one of these chromophores in polycarbonate has demonstrated an extremely high r 33 of 70 pm/V at 1550 nm. We believe that this is the largest r 33 reported at this wavelength.

New Organic Nonlinear Optical Polyene Crystals and Their Unusual Phase Transitions

“…Numerous molecular engineering investigation have already resulted in very large microscopic molecular nonlinearities of the nonlinear optical chromophores. [3][4][5][6] However, in most cases, highly nonlinear optical molecules tend to pack in a centrosymmetric or non-optimal arrangement in the crystalline solid state because of their large dipole moment. Moreover, their thermal stabilities are often not sufficient to apply melt-based crystal growth techniques, which are more attractive because of faster growth rates and generally better crystalline quality without solvent or solution inclusion problems associated with conventional solution growth.…”

Theoretical study on the mechanism of reaction between 3-hydroxy-3-methyl-2-butanone and malononitrile catalyzed by lithium ethoxide

“…2-dicyano methyl ene-4,5,5-trimethyl-2,5-dihydro furan-3-carbonitrile is a strong electron acceptor for nonlinear optics. It is a molecular building block for NLO material [2][3][4][5]. Li et al has reported its single-crystal structure [6].…”

Heterocyclic Nonlinear Optical Chromophores Composed of Phenothiazine or Carbazole Donor and 2-Cyanomethylene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran Acceptor

“…Particularly, 2-cyanomethylene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran (TCF) was well adopted as a strong electron acceptor that induces significantly high dipole moment (µ), first-order molecular hyperpolarizability (β), and their product (µβ). [8][9][10][11][12][13] In this report, we describe the synthesis and the microscopic nonlinear optical properties of two different types of the heterocyclic chromophores. Additional donor of diethylaminostyryl group was tethered to phenothaizine or carbazole that plays as conjugative donor bridge in DEA-PTZ-TCF and DEA-CBZ-TCF (see Figure 1).…”

“…2-Cyanomethylene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran (TCF) was commonly employed as a strong electron acceptor to induce strong charge transfer complex. [8][9][10][11][12][13] Energy state diagram to describe the highest occupied molecular orbital (HOMO) energy, the lowest unoccupied molecular orbital (LUMO) energy, and the bandgap were determined by electrochemical analysis and absorption spectroscopic method. The molecular 1 st -order hyperpolarizabilities and the dipole moments of the chromophores were calculated using semiempirical method.…”