Potential Nonlinear Optical Material Research Articles

2-Amino derivatives of 5-nitrophenylacetamide

The structures of the potential non-linear optical (NLO) materials N-[2-(iso­propyl­amino)-5-nitro­phenyl]­acet­amide, (I) C11H15N3O3, and N-[2-(butyl­amino)-5-nitro­phenyl]­acet­amide, (II) C12H17N3O3, have been investigated by X-ray analysis. To compare them with the structure of N-[2-(di­methyl­amino)-5-nitro­phenyl]­acet­amide, (III) C10H13N3O3, a known NLO compound, we had to redetermine the structure of (III), since it was described only briefly in the literature. There are two mol­ecules in the asymmetric unit of compound (I), which have different orientations of the substituents with respect to the benzene ring. The packing of mol­ecules in (II) and (III) contains stacks but both (I) and (II) crystallize in a centrosymmetric space group, which renders them inappropriate for NLO applications.

Thienyl(phenyl)iodonium Triflates—Structural, and Linear and Nonlinear Optical Behavior of Hypervalent Iodine Derivatives

The investigation of thienyl and bithienyl iodonium saltsas potential nonlinear optical materials is reported. Hypervalent iodine derivatives (see Figure) have been synthesized from the corresponding stannanes, and their structural, electronic, and preliminary nonlinear optical properties examined. UV analysis showed that the iodonium center mediates communication between the pendant aryl and heteroaryl functionalities.

Structure and properties of potential nonlinear optical materials

The synthesis, structure and properties of four ferrocene derivatives of 2-amino-1,2,3-triazole are reported. Solvatochromism is used as a screening process to assess the potential nonlinear optical behavior of these compounds. In general, this technique involves a number of assumptions, which may not be valid for organometallic complexes. Compound 3 crystallizes in space group P-1 with cell dimensions a = 5.771(2), b = 19.048(5), c = 19.343(5) A and α = 61.104(4), β = 88.410(5), γ = 89.858(5)°; compound 5 crystallizes in space group P21/c with cell dimensions a = 12.545(2), b = 13.308(2), c = 20.513(4) A and β = 104.035(3)°; compound 9 crystallizes in space group P21/n with cell dimensions a = 12.599(4), b = 14.734(4), c = 13.619(5) A, and β = 107.63(2); compound 11 crystallizes in space group P-1 with cell dimensions a = 7.638(3), b = 9.619(4), c = 12.692(5) A and α = 77.588(7), β = 78.416(7), γ = 71.357(7).

Polyarylates as nonlinear optics materials

Several polyarylates based on UV sensitive bisbenzylidenoketones for use as potential second-order nonlinear optical (NLO) materials have been obtained by interfacial polycondensation. The polymers investigated can be divided into two groups: guest-host systems and polyarylates with NLO side-chains. The electro-optic (EO) coefficient, r 33, was measured in the Pockels experiment. UV crosslinking was applied to increase NLO stability of the investigated materials. Loss and time relaxation of EO coefficient for crosslinked and noncrosslinked polyarylates were also measured.

The First Electron‐Donor‐Acceptor Paracyclophanes with Ferrocene NLO‐Phores: Synthesis, Absorption and Electrochemical Properties

AbstractAs potential nonlinear optical material. 12‐nitro‐4,7‐bis(2‐ferrocenylvinyl)[2.2]paracyclophane (1) and 12‐nitro‐4,5,7,8‐tetrakis(2‐ferrocenylvinyl)[2.2]paracyclophane(2) have been synthesized by pd‐catalyzed coupling reactions of vinylferrocene with the precursor cyclophanes 9 and 13, respectively. The absorption and electrochemical properties of 1 and 2 are also described.

Synthesis of ferrocenylarylethylenes and their cyclodextrin complexes, which are potential materials for nonlinear optics

Cis- andtrans-isomers of 1-ferrocenyl-2-(2-(4-)nitrophenyl)ethylenes and their complexes with β-cyclodextrin have been synthesized with the aim of studying their nonlinear optical properties.

Crystal structure of 1-ethyl-2,6-dimethyl-4(1 H)-pyridinone, trihydrate: a potential nonlinear optical crystalline organic material transparent till the near ultraviolet range

Abstract The 1-ethyl-2, 6-dimethyl-4(1 H)-pyridinone, trihydrate C9H13NO · 3H2O (EDMP) is a potential nonlinear optical crystalline material for second harmonic generation till the near ultraviolet region, crystallizing in the monoclinic space group Cc with Z = 4 and the unit cell parameters a = 8.382(1) Å, b = 19.275(2) Å, c = 7.220(3) Å, β = 104.56(2)°. The crystal structure was solved by direct methods and refined by least squares to R = 0.026 using 862 non equivalent reflections. EDMP molecules lying in planes parallel to (001) are linked through O–H---O and C–H---O bonds with the water molecule network. Layers are built from adjacent five and seven-membered rings of the water molecules and EDMP oxygen atoms forming a semiclathrate structure.

A 1:2 addition compound of cadmium bromide with 3-methyl-4-nitropyridine N-oxide

catena-Poly[bis(3-methyl-4-nitropyridine N-oxide-O)cadmium-di-μ-bromo], [Cd(C 6 H 6 N 2 O 3 ) 2 Br 2 ], which belongs to a group of potential nonlinear optical materials, crystallizes in the non-centrosymmetric space group Fdd2. The Cd atom is octahedrally coordinated to two O atoms from the trans 3-methyl-4-nitropyridine N-oxide ligands in the axial positions and four Br atoms lying in the equatorial plane. The coordination octahedra form one-dimensional chains along the short c axis by edge-sharing through the Br atoms, with each Cd atom located on a crystallographic diad axis

4-Nitrophenylhydrazones of partially formylated polystyrene, their properties and crosslinking

The title polymers were prepared as potential non-linear optical materials with a degree of substitution 3–13 mole %. During UV-irradiation and/or heating near the glass transition temperature these polymers crosslink through the hydrazone groups and their UV-vis absorption band diminishes. Degrees of crosslinking of swollen samples were estimated. A possibility of simultaneous crosslinking and poling of these polymers is discussed.

Electron donor-acceptor complexes as potential high-efficiency second-order nonlinear optical materials. A computational investigation

The second-order nonlinear optical response of model molecular 1:1 and asymmetric 2:1 organic [pi] electron donor-acceptor (EDA) complexes is investigated using the INDO/S sum-over-excited particle-hole-states formalism. It is found that intermolecular charge-transfer transitions in EDA complexes represent a promising approach to achieving sizable second-order optical nonlinearities. Calculated hyperpolarizabilities may be generally related to the strength of the donor-acceptor interaction in the complex, affording for a given acceptor, the largest values in the case of aminoarene donors. The large change in dipole moment that accompanies intermolecular charge-transfer transitions and the relatively low-lying charge-transfer excitation energies are the major sources of the large calculated second-order nonlinearities. The relative orientation of donor and acceptor components is also an important feature, leading to stabilization of the ground state as well as to maximization of the oscillator strength of the lowest energy charge-transfer excitation and, in turn, the NLO response. In the case of asymmetric 2:1 EDA complexes, calculated hyperpolarizability enhancements over the 1:1 complexes can be related to the red-shift of the charge-transfer excitation as well as to an increase in dipole moment change between ground and excited states. The perturbation theoretical two-level' model is a useful first approximation for predicting the second-order nonlinearmore » response of such complexes. 29 refs., 2 figs., 3 tabs.« less

Nonlinear Optical Properties of Chloronitroanilines

ABSTRACTA series of chloronitroaniline compounds were investigated as bulk crystals and in thin film form as potential nonlinear optical materials for use in electro-optic devices. Crystal structure determination and computational modelling were completed on 5- chloro-2-nitroaniline and electro-optic measurements were performed on crystals grown by physical vapor deposition. Second harmonic generation measurements were carried out on poled guest/host systems of 3-chloro-4-nitroaniline in poly(methylmethacrylate).