Synthesis, optical and nonlinear optical properties of new pyrazoline derivatives

Myśliwiec, Jarosław; Szukalski, Adam; Sznitko, Lech; Miniewicz, Andrzej; Haupa, Karolina Anna; Zygadlo, K.; Matczyszyn, Katarzyna; Olesiak‐Bańska, Joanna; Samoć, Marek

doi:10.1016/j.dyepig.2013.10.027

Cited by 39 publications

(27 citation statements)

References 19 publications

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“…The synthesis method is described elsewhere, 17,18 and the PY-oCNNO 2 molecular structure is shown in Figure 1. The PY-oCNNO 2 molecule possesses an aromatic ring serving as the electrondonating group, a pyrazole ring, and two different acceptor groups substituted on its other side.…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

Photoinduced Birefringence in PMMA Polymer Doped with Photoisomerizable Pyrazoline Derivative

et al. 2015

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Upon S 0 −S 1 excitation, the pyrazoline derivative molecule (Z)-2-(4-nitrophenyl)-3-(1-phenyl-4,5-dihydro-1H-pyrazol-3-yl)acrylonitrile, abbreviated as PY-oCNNO 2 , can be transformed from its ground state trans (E) form to bended cis (Z) form. Similar to the case of the well-known family of the photochromic azobenzenes, such a molecular property can be employed to fabrication of photochromic polymers by suitable doping of the chromophores into polymer matrix. In this work, we prepared poly(methyl methacrylate) thin films doped with PY-oCNNO 2 and measured the characteristic for optical switchers dynamic and static photoinduced birefringence (PIB) phenomenon. Possible conformational states of PY-oCNNO 2 , energy barriers, and associated dipole moments were calculated using TD-DFT quantum chemical methods. The presented experiments show that pyrazoline derivatives constitute a prospective group of materials with a great potential for photonic applications.

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Section: ■ Materials and Methodsmentioning

confidence: 99%

Photoinduced Birefringence in PMMA Polymer Doped with Photoisomerizable Pyrazoline Derivative

et al. 2015

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“…Melting points were determined using a Thermo Scientific C NMR (100 MHz) spectra of compounds (in dimethyl sulfoxide, DMSO-d 6 ) were recorded at room temperature on a Bruker Ultra Shield 400. Peak multiplicities were designed as: s, singlet; d, doublet; t, triplet; m, multiplet; dd, double doublet.…”

Section: Methodsmentioning

confidence: 99%

“…Reports in the literature include studies on solvatochromic effect and electrochemical, photophysical, optical and nonlinear optical properties. [5][6][7][8][19][20][21][22] Following our research on the synthesis and evaluation of potential applications of pyrazole derivatives, 23,24 and the growing interest in the development of luminescence small molecules as emitting materials and biology research, [5][6][7][8][19][20][21][22][23][24][25] we report a series of pyrazoline derivatives incorporating methoxyl, an electron donor group, naphthyl and phenyl substituents as chromophores, on the π-conjugated structure and analysis of absorption/emission properties of these compounds.…”

Section: Introductionmentioning

confidence: 99%

“…[5][6][7][8] The building of these N-heterocycles systems, from simple reactions, using small molecules and compatible with multicomponent, regioselective, eco-friendly and efficient synthetic procedures, which include variations to conventional methods, allows to incorporate specific structural characteristics. [9][10][11][12][13][14] Substituents of different nature, electron withdrawing group (EWG) and electron releasing group (ERG), in aromatic aldehydes, ketones and hydrazines, make them versatile synthetic auxiliaries in classical organic synthesis.…”

Section: Introductionmentioning

confidence: 99%

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Syntheses, Experimental and Theoretical Studies on Absorption/Emission Properties of Pyrazoline-Containing Aryl/Methoxynaphthyl Substituents

Trilleras¹,

González-López²,

León-Jaramillo³

et al. 2017

J. Braz. Chem. Soc.

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5-Aryl-3-(2-methoxynaphthalen-6-yl)-1-phenylpyrazoline derivatives were synthesized starting from (E)-1-(3-aryl)-(2-methoxynaphthalen-6-yl)-prop-2-en-1-one and phenylhydrazine. The compounds were characterized by 1 H and 13 C nuclear magnetic resonance (NMR), elemental analyses and mass spectrometry. Some compounds showed promising luminescence properties in solution and in solid state; the absorption and emission characteristics were measured and the fluorescence quantum yield of two of the derivatives [4,5-dihydro-3-(2-methoxynaphthalen-6-yl)-5-(3,4,5-trimethoxyphenyl)-1-phenyl-1H-pyrazoline and 5-(4-chlorophenyl)-4,5-dihydro-3-(2-methoxynaphthalen-6-yl)-1-phenyl-1H-pyrazoline] were found to have excellent values compared to rhodamine B standard. Theoretical calculations at time-dependent density functional theory (TD-DFT) level are in agreement with the experimental measurements and are helpful to explain the electronic behavior.

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“…Nitrogen based heterocyclic compounds are of special interest, as they constitute an important class of natural and synthetic products and many of them exhibit useful biological activities and unique electrical and optical properties [18][19][20][21][22]. On the other hand, pyrazoline group substituted with heterocyclic compounds at 3-position of carbon atom possess considerable changes in photo-physical behaviors.…”

Section: Introductionmentioning

confidence: 99%

Highly fluorescent semiconducting pyrazoline materials for optoelectronics

Vanaraj

Kannan

2015

Optical Materials

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Synthesis, optical and nonlinear optical properties of new pyrazoline derivatives

Cited by 39 publications

References 19 publications

Photoinduced Birefringence in PMMA Polymer Doped with Photoisomerizable Pyrazoline Derivative

Photoinduced Birefringence in PMMA Polymer Doped with Photoisomerizable Pyrazoline Derivative

Syntheses, Experimental and Theoretical Studies on Absorption/Emission Properties of Pyrazoline-Containing Aryl/Methoxynaphthyl Substituents

Highly fluorescent semiconducting pyrazoline materials for optoelectronics

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