Structures of 2,6-bis(benzylidene)cyclohexanone (III) and 3,5-bis(4-dimethylaminobenzylidene)-1-methyl-4-piperidone (IV)

Zeng, Jia; Quail, J. Wilson; Arora, Vinod; Dimmock, J. R.

doi:10.1107/s0108270188011345

Cited by 35 publications

(29 citation statements)

References 4 publications

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“…Single-crystal X-ray analysis shows "equatorial", "axial", and intermediate structures. 49,50,57,62,64 The energy difference between two conformations, estimated through B3LYP/6-31G** or HF/6-31G** calculations, does not exceed 3 kJ/mol, which may imply that in solution at roomtemperature one could find a statistical mixture of both conformers. Therefore, we study both "equatorial" and "axial" structures of compounds 5-8 with strong TPA absorbancies to consider the impact of the conformational geometry on the optical properties of the chromophores.…”

Section: Resultsmentioning

confidence: 99%

“…57-60 Structural characteristics of cyclohexanones and piperidones have been described in numerous publications. 56,57,[61][62][63][64][65] Spectral characteristics, including OPA, TPA and fluorescence of some of those compounds, have also been investigated. [58][59][60]66 However, despite these extensive experimental studies, theoretical investigations of these molecular structures have not been done yet.…”

Section: Introductionmentioning

confidence: 99%

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Role of Donor−Acceptor Strengths and Separation on the Two-Photon Absorption Response of Cytotoxic Dyes: A TD-DFT Study

Badaeva

Timofeeva²,

Masunov³

et al. 2005

J. Phys. Chem. A

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Time-dependent density functional theory (TD-DFT) is applied to model one-photon (OPA) and two-photon (TPA) absorption spectra in a series of conjugated cytotoxic dyes. Good agreement with available experimental data is found for calculated excitation energies and cross sections. Calculations show that both OPA and TPA spectra in the molecules studied are typically dominated by two strong peaks corresponding to different electronic states. We find that donor-acceptor strengths and conjugated bridge length have a strong impact on the cross-section magnitudes of low-and high-frequency TPA maxima, respectively. These trends are analyzed in terms of the natural transition orbitals of the corresponding electronic states. Observed structureproperty relationships may have useful implications on design of organic conjugated chromophores with tunable two-photon absorption properties for photodynamic therapy applications.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Role of Donor−Acceptor Strengths and Separation on the Two-Photon Absorption Response of Cytotoxic Dyes: A TD-DFT Study

Badaeva

Timofeeva²,

Masunov³

et al. 2005

J. Phys. Chem. A

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“…Both DMABA and DMABC appear to be symmetrical so that, with two and four molecules per unit cell, a centrosymmetric space group seems to be likely. In fact, for the structurally rather similar compounds of the same class of bis(benzylidene)ketones, namely 2,6-bis(benzylidene)cyclohexanone and 3,5-bis[4-(dimethylamino)benzylidene]-1 -methyl-4-piperidone, centrosymmetric crystal structures have been determined (Jia, Quail, Arora & Dimmock, 1989).…”

Section: Discussionmentioning

confidence: 99%

The Use of Structure Analysis Methods in Combination with Semi-empirical Quantum-Chemical Calculations for the Estimation of Quadratic Nonlinear Optical Coefficients of Organic Crystals

Yakimanski¹,

Kolb²,

Matveeva³

et al. 1997

Acta Cryst Sect A

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An effective search for new organic crystals for prospective use in nonlinear optical (NLO) applications requires quantitative and fast experimental determination of their NLO properties at a molecular level. However, the growth of sufficiently large single crystals, which are needed for structural analysis and refinement by X-ray methods, is a time-consuming and sometimes impossible task. Single crystals of a considerably smaller size may be effectively used for complete structural analysis by electron diffraction combined with simulation methods. When the crystal structure of a given compound is known, its NLO properties may be estimated using quantum-chemical methods for calculation of the molecular nonlinearity tensor and the relationships between its components and the macroscopic coefficients of the crystalline nonlinearity tensor. In the present work, the semiempirical PM-3 method was employed for this aim.

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“…etween the phenyl rings [15]. This lack of coplanarity which originates from the twist between the aryl rings and adjacent olefinic groups is regarded as the result of the repulsive interactions between the hydrogen atoms of the aryl rings and equatorial hydrogen atoms from cyclohexyl ring [e.g., 13].…”

Section: Resultsmentioning

confidence: 99%

Novel Synthesis and Crystal Structures of Two α, α′-bis-Substituted Benzylidene Cyclohexanones: 2,6-Bis-2-nitro(benzylidene)cyclohexanone and 2,6-Bis-4-methyl(benzylidene)cyclohexanone

et al. 2011

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Structures of 2,6-bis(benzylidene)cyclohexanone (III) and 3,5-bis(4-dimethylaminobenzylidene)-1-methyl-4-piperidone (IV)

Cited by 35 publications

References 4 publications

Role of Donor−Acceptor Strengths and Separation on the Two-Photon Absorption Response of Cytotoxic Dyes: A TD-DFT Study

Role of Donor−Acceptor Strengths and Separation on the Two-Photon Absorption Response of Cytotoxic Dyes: A TD-DFT Study

The Use of Structure Analysis Methods in Combination with Semi-empirical Quantum-Chemical Calculations for the Estimation of Quadratic Nonlinear Optical Coefficients of Organic Crystals

Novel Synthesis and Crystal Structures of Two α, α′-bis-Substituted Benzylidene Cyclohexanones: 2,6-Bis-2-nitro(benzylidene)cyclohexanone and 2,6-Bis-4-methyl(benzylidene)cyclohexanone

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