The Dipole Moments and Molecular Structures of Croconic Acid and Dimethyl Croconate

Washino, Masamitsu; Yamada, Kiyoyuki; Kurita, Yukio

doi:10.1246/bcsj.31.552

Cited by 10 publications

(5 citation statements)

References 4 publications

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“…They are 9.27 and 9.24 Debye from the experimental multipole model refinement and for the refinement of theoretical structure factors respectively. Both agree very well with the experimental value of 9–10 Debye obtained in solution 29. Another important result is the direction of the dipole moment within the crystal.…”

Section: Topological Analysis Of the Charge Densitysupporting

confidence: 89%

Charge Density Analysis of an Organic Ferroelectric. Croconic Acid: an Experimental and Theoretical Study

Zhurov

Pinkerton

2013

Zeitschrift anorg allge chemie

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The charge density in the high density (ρ = 1.912 g·cm -3 ) organic ferroelectric, croconic acid, was determined from low temperature (20 K) X-ray diffraction data, and DFT theoretical calculations. The high density was associated with strong intermolecular interaction IntroductionThe recent discovery of the ferroelectric properties of croconic acid (4,5-dihydroxy-4-cyclopentene-1,2,3-trione, C 5 H 2 O 5 ) crystals [1] has solicited new interest in this high density (ρ = 1.912 g·cm -3 ) organic compound, both in applications and research science. For example, a successful attempt has recently been made to deposit thin films of croconic acid using Matrix-assisted pulsed laser deposition (MAPLE). [2] Additional density functional theoretical calculations, [3,4] X-ray photoelectron spectroscopy combined with ab initio methods, [5] as well as studies by NQR and NMR spectroscopy [6] reflect the increasing attraction of this compound in the last two years. Although croconic acid has been known since 1825, when it was discovered by L. Gmelin [7] who named it "croconic" due to its yellow color, and despite being used as a colorant and for preparation of various dyes for a long time, the publication of its crystal structure first appeared in 2001. [8] This work was followed by further structural studies on the monovalent [Li + , K + , Na + , Rb + , Cs + , (NH 4 ) + ] cation salts and croconic acid itself [9] to understand the nature of hydrogenbond interactions and packing forces in such crystals. Nevertheless, the investigation of the charge density distribution in the croconic acid crystal has not been reported.In this paper we present an extensive study of the electron density distribution and its derivatives to gain insight into the high density and ferroelectric properties of this compound. Three different methods were applied and the results compared with each other: data obtained from a precise X-ray diffraction * Prof. Dr. A. A. Pinkerton Fax: +1-419-530-4033 E-Mail: A.Pinkerton@utoledo.edu [a]1969 energies. The spontaneous polarization is correlated with the derived molecular dipole moment (9.3 Debye). Improvements in multipole refinement protocols are described. Limitations in the multipole model with respect to heteronuclear bond properties are discussed.

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Section: Topological Analysis Of the Charge Densitysupporting

confidence: 89%

Charge Density Analysis of an Organic Ferroelectric. Croconic Acid: an Experimental and Theoretical Study

Zhurov

Pinkerton

2013

Zeitschrift anorg allge chemie

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“…A single croconic acid molecule is electrically polar with a dipole moment of 7-7.5 D (1 D = 3.336 Â 10 À30 C m). 96,97 The dipole moment is due to the electronegativity difference between the two hydrogen and oxygen atoms present in the hydroxyl groups attached to the CQC unit. Furthermore, the relative orientations of the H atoms in the hydroxyl group define the isomeric forms with distinct dipole moments.…”

Section: Structure Of An Individual Croconic Acid Moleculementioning

confidence: 99%

Organic ferroelectric croconic acid: a concise survey from bulk single crystals to thin films

Mohapatra¹,

Cherifi‐Hertel²,

Kumar³

et al. 2022

J. Mater. Chem. C

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“…In the present work, TGS crystals doped with CA molecules, which have a large dipole moment d ~(9-10) Debye [36], were grown. The temperature dependences of the permittivity of a TGS:CA crystal grown from a solution with a weight content of 98:2 components are shown in Figure 11b.…”

Section: Photoluminescencementioning

confidence: 99%

“…The anion exhibits aromaticity, stabilized by electron delocalization of π electrons around the ring. The CA molecule is characterized by a flat topology and a large value of the electric dipole moment (~9 Debye [36]). Due to its relatively small size (~0.5 nm), it can be incorporated into various crystal structures and affect the structural, optical and dielectric properties of the host substance.…”

Section: Introductionmentioning

confidence: 99%

Croconic Acid Doped Triglycine Sulfate: Crystal Structure, UV-Vis, FTIR, Raman, Photoluminescence Spectroscopy, and Dielectric Properties

et al. 2022

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Triglycine sulfate (TGS) single crystals doped with croconic acid (CA) were grown by evaporation from aqueous solutions. X-ray diffraction analysis shows a slight reduction in unit cell volume in TGS:CA compared to pure TGS crystals. The polarized Raman and near-infrared absorption spectra show that the positions of most lines resulting from inter- and intramolecular vibrations are in good agreement with those in spectra of undoped TGS crystals. The inclusion of CA in TGS is confirmed by the presence of bands characteristic of CA in the infrared-Fourier transform spectra. The ultraviolet-visible absorption spectra of TGS:CA are characterized by the presence of additional absorption bands (compared to the spectra of pure TGS) located in the transparent region of pure TGS. In the photon energy region 1.6–3.6 eV, a strong “green” luminescence band is present in TGS:CA upon excitation at λ = 325 nm. The position of the emission band depends on the wavelength of the exciting light. Doping of TGS with CA causes pinning of domain walls, which is accompanied by a decrease in amplitude and frequency dispersion of the dielectric anomaly at the phase transition, a decrease in the switchable polarization and an increase in the coercive field of hysteresis loops.

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The Dipole Moments and Molecular Structures of Croconic Acid and Dimethyl Croconate

Cited by 10 publications

References 4 publications

Charge Density Analysis of an Organic Ferroelectric. Croconic Acid: an Experimental and Theoretical Study

Charge Density Analysis of an Organic Ferroelectric. Croconic Acid: an Experimental and Theoretical Study

Organic ferroelectric croconic acid: a concise survey from bulk single crystals to thin films

Croconic Acid Doped Triglycine Sulfate: Crystal Structure, UV-Vis, FTIR, Raman, Photoluminescence Spectroscopy, and Dielectric Properties

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