Crystal Structure and (Non)linear Optical Properties of a Cyanuric Acid Isoniazid &lt;1/1&gt; Co-crystal: Shortcomings of Phase Matching Determination from Powdered Samples

Wojnarska, Joanna; Gryl, Marlena; Seidler, Tomasz; Rydz, Agnieszka; Oszajca, Marcin; Stadnicka, Katarzyna; Marzec, M.; Matulková, Irena; Němec, Ivan; Němec, Petr

doi:10.1021/acs.cgd.9b01023

Cited by 10 publications

(11 citation statements)

References 28 publications

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“…The theoretically determined values of refractive indices were compared with experimental measurements carried out using a microscopic immersion oil method; details of such an experiment are described in the Supporting Information as well as in some of our earlier works. 26 As most of the examined crystals were needle-shaped, subsequent measurements of the linear birefringence using an Ehringhaus compensator were necessary to confirm the observed values of refractive indices. Additional difficulties in the measurements were encountered for STZ2ap and STZ2a5mp, where placement of the crystals in some immersion oils caused slow but persistent recrystallization (see Figure S2).…”

Section: Methodsmentioning

confidence: 99%

“…The situation in a crystal can be more complex due to optical anisotropy. The alterations of refractive indices with respect to crystal directions have been proven to be strongly influenced by the packing of molecules in the solid state. − The orientation of building blocks in a crystal structure is still difficult to predict, especially in dealing with multicomponent materials. From the viewpoint of materials design it would be ideal to find a perfect arrangement of the molecules in the solid state and tune the properties by selectively changing one or more substituents while retaining the original crystal packing.…”

Section: Introductionmentioning

confidence: 99%

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Effect of Substituent Exchange on Optical Anisotropy in Multicomponent Isostructural Materials Containing Sulfathiazole and 2-Aminopyridine Derivatives

Wojnarska

Gryl

Seidler

et al. 2020

Crystal Growth & Design

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Four isostructural, multicomponent materials containing sulfathiazole and 2-aminopyridine substituted in the para position by H/CH 3 /Cl/Br have been investigated. The crystal structures of these solids were determined using data from singlecrystal X-ray diffraction measurements. The similarity of the crystal packing was studied using XPac and CrystalCMP programs as well as the packing similarity tool implemented in the Mercury software. The analysis of quantitative similarity parameters showed that the least similar geometrical arrangement is observed for H → Br interchange, while Cl → CH 3 exchange has the smallest influence on the molecular packing. These can be easily explained by the differences in the size and properties of the 2aminopyridine substituent. Refractive indices of all materials were measured using the immersion oil method and calculated using the (Q)LFT approach. The observed variations in refractive indices were discussed in relation to the packing of the structural components and were correlated with the variations in polarizabilities of 2-aminopyridine derivatives.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Effect of Substituent Exchange on Optical Anisotropy in Multicomponent Isostructural Materials Containing Sulfathiazole and 2-Aminopyridine Derivatives

Wojnarska

Gryl

Seidler

et al. 2020

Crystal Growth & Design

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“…The results clearly confirm the possibility of SHG phase matching for this salt. The small discrepancy between the two smallest fractions can be explained by problems in preparing powders with isometric particles and effective control of the particle size in the family of soft molecular crystals, which are quite common (e.g., [22,39,40]).…”

Section: Thermal Behaviourmentioning

confidence: 99%

Inorganic Salts of N-phenylbiguanidium(1+)—Novel Family with Promising Representatives for Nonlinear Optics

Matulková

Cı́sařová

Fridrichová

et al. 2021

IJMS

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Seven inorganic salts containing N-phenylbiguanide as a prospective organic molecular carrier of nonlinear optical properties were prepared and studied within our research of novel hydrogen-bonded materials for nonlinear optics (NLO). All seven salts, namely N-phenylbiguanidium(1+) nitrate (C2/c), N-phenylbiguanidium(1+) perchlorate (P-1), N-phenylbiguanidium(1+) hydrogen carbonate (P21/c), bis(N-phenylbiguanidium(1+)) sulfate (C2), bis(N-phenylbiguanidium(1+)) hydrogen phosphate sesquihydrate (P-1), bis(N-phenylbiguanidium(1+)) phosphite (P21), and bis(N-phenylbiguanidium(1+)) phosphite dihydrate (P21/n), were characterised by X-ray diffraction (powder and single-crystal X-ray diffraction) and by vibrational spectroscopy (FTIR and Raman). Two salts with non-centrosymmetric crystal structures—bis(N-phenylbiguanidium(1+)) sulfate and bis(N-phenylbiguanidium(1+)) phosphite—were further studied to examine their linear and nonlinear optical properties using experimental and computational methods. As a highly SHG-efficient and phase-matchable material transparent down to 320 nm and thermally stable to 483 K, bis(N-phenylbiguanidium(1+)) sulfate is a promising novel candidate for NLO.

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“…Recently, some of us have proven difficulties in studying the nonlinear optical properties of elongated crystals using the Kurtz−Perry technique. 34 Among the most investigated organic molecules regarding NLO efficiency, there are derivatives of aniline and N,Ndialkylaniline. 35 In this study, cadmium iodide was combined with 2,5-and 2,6-dimethylaniline.…”

Section: ■ Introductionmentioning

confidence: 99%

Dimethylaniline-Based Hybrid Compounds of Cadmium Diiodide: Synthesis, Crystal Structure, and Physical Properties

Duda

Gryl

Miniewicz

et al. 2022

Crystal Growth & Design

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In this work, synthesis, crystal structure, and selected properties of two new organic−inorganic compounds based on cadmium iodide with 2,5-and 2,6-dimethylaniline: CdI 2 (2,5-DMA) 2 1 and CdI 2 (2,6-DMA) 2 2, respectively, were investigated. Both compounds were obtained using the same methodology, and their crystal structures were determined from powder (1) and single-crystal (2) X-ray diffraction experiments. The examined materials crystallize in the noncentrosymmetric space group Fdd2 and contain large polarizable iodine ions and electron-rich aromatic ligands. Second harmonic generation (SHG) tests performed with urea as a reference revealed high SHG efficiency of powdered samples 1 and 2. SHG signals measured for samples 1 and 2 are, respectively, around 10 and 8 times larger than the signal for urea. The experimental part was supplemented with theoretical calculations of the second-order electric susceptibility tensor components, χ ijk (2) . Calculated values of the χ 113 (2) tensor component around 1.2−1.4 pm•V −1 suggest that both materials are relatively efficient second harmonic generators. Fibrous morphology of the materials was revealed by scanning electron microscopy (SEM), and the observed bending of the fibers suggested their significant flexibility. Samples 1 and 2 were also characterized by spectroscopic techniques (IR, RS, UV−Vis-DRS) and their thermal stability and decomposition rates were researched using XRPD and TG/DSC, revealing that both investigated materials are thermally stable up to around 100 °C.

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Crystal Structure and (Non)linear Optical Properties of a Cyanuric Acid Isoniazid <1/1> Co-crystal: Shortcomings of Phase Matching Determination from Powdered Samples

Cited by 10 publications

References 28 publications

Effect of Substituent Exchange on Optical Anisotropy in Multicomponent Isostructural Materials Containing Sulfathiazole and 2-Aminopyridine Derivatives

Effect of Substituent Exchange on Optical Anisotropy in Multicomponent Isostructural Materials Containing Sulfathiazole and 2-Aminopyridine Derivatives

Inorganic Salts of N-phenylbiguanidium(1+)—Novel Family with Promising Representatives for Nonlinear Optics

Dimethylaniline-Based Hybrid Compounds of Cadmium Diiodide: Synthesis, Crystal Structure, and Physical Properties

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