Preparation and Structural Evaluation of the Conformational Polymorphs of α-[(4-Methoxyphenyl)methylene]-4-nitrobenzeneacetonitrile

Vrcelj, Ranko M.; Shepherd, E.E.A.; Yoon, Choon Sup; Sherwood, J. N.; Kennedy, Alan R.

doi:10.1021/cg025529h

Cited by 23 publications

(55 citation statements)

References 19 publications

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“…158–159 °C; 1 H NMR (400 MHz, CDCl 3 ): δ =8.30 (d, J= 8.8 Hz, 2 H), 7.96 (d, J= 8.8 Hz, 2 H), 7.82 (d, J= 8.8 Hz, 2 H), 7.61 (s, 1 H), 7.02 (d, J= 8.8 Hz, 2 H), 3.90 ppm (s, 3 H). The data were in agreement with the literature …”

Section: Methodssupporting

confidence: 92%

“…The data were in agreement with the literature. [15] Compounds 6a-6i were synthesized using p-substituted 2-phenylacetonitriles 1a-1f and aldehydes 3a-3c as substrates according to the procedure given above for compound 5a [When nitro-substituted 2-(4-nitrophenyl)acetonitrile (1c)w as used, NaOCH 3 (0.05 equiv) was required. When the solubility for some substrates was not good in EtOH, THF was added to increase the solubility.…”

Section: Experimental Section Generali Nformationmentioning

confidence: 99%

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Facile Preparation of α‐Cyano‐α,ω‐Diaryloligovinylenes: A New Class of Color‐Tunable Solid Emitters

Zhang

et al. 2015

Chemistry An Asian Journal

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An efficient Knoevenagel condensation reaction was used to construct a series of α-cyano-α,ω-diaryloligovinylenes, which show prominent fluorescence emission in the solid state. On investigating the effect of conjugation length on fluorescent properties, we found that the diene structure showed superior solid-state luminescence. Furthermore, the emission color could be adjusted by introducing donor or acceptor functional groups at the terminal aryl groups. Full-color emission in the visible region can be achieved by adding different functional groups to the α-cyano-α,ω-diaryldivinylene moiety. The structure-property relationships were elucidated and some observations such as the substitution position effects were discussed. These compounds have potential applications as full-color solid emissive candidates in material science and their simple structures allow them to be easily modified resulting in further interesting properties.

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Section: Methodssupporting

confidence: 92%

Section: Experimental Section Generali Nformationmentioning

confidence: 99%

Facile Preparation of α‐Cyano‐α,ω‐Diaryloligovinylenes: A New Class of Color‐Tunable Solid Emitters

Zhang

et al. 2015

Chemistry An Asian Journal

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“…also gives an opportunity to obtain acentric NLO crystals. [15][16][17] Another strategy to encourage polar organic molecules to be crystallized in acentric space groups is the use of strong [18][19][20] and even weak 21 hydrogen-bond interactions. We used the latter strategy in our present study for formation of acentric NLO crystalline materials.…”

Section: Introductionmentioning

confidence: 99%

Thermally Stable Imines as New Potential Nonlinear Optical Materials

Nesterov

Antipin

Нестеров

et al. 2004

Crystal Growth & Design

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In the search for new thermostable acentric nonlinear optical (NLO) crystalline materials, several polar imine derivatives with the general structure D-π-A(D′) were synthesized and studied. Introduction of the amino group (D′) into the acceptor moiety of these molecules was supposed to bring hydrogen bonds into the crystal structures, and so to elevate their melting points and to assist acentric molecular packings. Ten compounds of this type have been prepared, and for six of them single crystals have been grown and characterized by X-ray diffraction analysis. High melting points were found for all synthesized compounds. It was found that four compounds have acentric crystal structures. Analysis of the crystal packing and hydrogen bonding in the compounds studied has been carried out along with quantum calculations of the molecular NLO responses. This allowed an understanding of the thermal stability of the compounds studied and some of their NLO characteristics.

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“…The bulk crystalline phases of such crystals have three possible polymorphic forms, two being noncentrosymmetric with a very similar unit-cell crystal geometry (forms (a) and (b)) [10,11,12]. The preparation of the organic nanocrystals in sol-gel glasses relies on the control of the nucleation and growth kinetics of the dye confined in the pores of the gel [10].…”

mentioning

confidence: 99%

In SituDiagnostics of the Crystalline Nature of Single Organic Nanocrystals by Nonlinear Microscopy

Brasselet¹,

Floc’h²,

Treussart³

et al. 2004

Phys. Rev. Lett.

133

156

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We elucidate the crystalline nature and the three-dimensional orientation of isolated organic nanocrystals embedded in a sol-gel matrix, using a polarized nonlinear microscopy technique that combines two-photon fluorescence and second harmonic generation. This technique allows the distinction between mono-crystalline structures and nano-scale poly-crystalline aggregates responsible for incoherent second harmonic signals.PACS numbers: 78.67. Bf, 61.82.Rx The optical properties of nanoparticles have recently attracted much attention. In addition to metallic and semiconductor nanoparticles which are now used as biomarkers and as the building blocks of nanostructured materials [1], their organic counterparts constitute an interesting alternative. Advances in molecular engineering have enabled the design of molecular structures of various resonances and symmetries with optimized one-and two-photon absorption cross sections [2], or combining different optical properties such as luminescence and second harmonic generation (SHG) [3]. In addition, macroscopic molecular arrangements have been optimized using the tensorial oriented gas model [4], which predicts that an enhancement of the SHG efficiency is expected from the non-centrosymmetric crystalline arrangement of efficient nonlinear molecules. Molecular nanocrystals can be therefore envisioned as a new class of multi-functional nano-scale materials. In the case of organic nanocrystals however, the traditional crystalline characterization techniques have raised many practical barriers due to their low concentration and fragility. Consequently, the elucidation of their crystalline nature has been so far indirect or averaged over a large number of nanocrystals [5].In this letter, we show that two-photon nonlinear microscopy permits in-situ characterization of isolated organic nanocrystals grown in an amorphous sol-gel matrix. The diagnostic is based on polarization resolved two-photon excited fluorescence (TPF) and SHG. TPF is an incoherent process allowed in centrosymmetric media, which exhibits a specific anisotropy depending on the medium symmetry. On the other hand, SHG is the signature of a crystalline non-centrosymmetric phase in the sample, with a sensitivity down to the nanometric scale [6,7]. We show that the polarization analysis of both TPF and SHG from nanocrystals allows the unambiguous discrimination between isolated mono-crystalline and poly-crystalline systems. Moreover, once a nanocrystal has been identified as mono-crystalline, a detailed model for both TPF and SHG polarization responses accounting for the unit-cell symmetry allows the determination of its three-dimensional orientation within the host matrix.The organic nanocrystals that we investigate are based upon the α-((4'-methoxyphenyl)methylene)-4-nitro-benzene-acetonitrile) molecule (CMONS), which exhibits efficient luminescence and quadratic nonlinearity under two-photon excitation [8,9,10]. The bulk crystalline phases of such crystals have three possible polymorphic forms, two being noncen...

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Preparation and Structural Evaluation of the Conformational Polymorphs of α-[(4-Methoxyphenyl)methylene]-4-nitrobenzeneacetonitrile

Cited by 23 publications

References 19 publications

Facile Preparation of α‐Cyano‐α,ω‐Diaryloligovinylenes: A New Class of Color‐Tunable Solid Emitters

Facile Preparation of α‐Cyano‐α,ω‐Diaryloligovinylenes: A New Class of Color‐Tunable Solid Emitters

Thermally Stable Imines as New Potential Nonlinear Optical Materials

In SituDiagnostics of the Crystalline Nature of Single Organic Nanocrystals by Nonlinear Microscopy

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