The Crystal Structure of Phenylmalondialdehyde at -162 degrees C.

Semmingsen, Dag; Sydnes, Leiv Kr.; Wennerström, Olof; Jensen, R. B.; Schroll, Gustav; Williams, D. H.; Pilotti, Anne‐Marie

doi:10.3891/acta.chem.scand.31b-0114

Cited by 28 publications

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“…In this work, we focus on 1-cyclobutene-1,2-dicarboxylic acid (CBDC, C 6 H 6 O 4 ) [12] and 2-phenylmalondialdehyde (PhMDA, C 9 H 8 O 2 ) [13]. Initial x-ray diffraction studies of CBDC [12] and PhMDA [13] were performed only at room temperature for CBDC and at T =111 K for PhMDA.…”

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confidence: 99%

“…Initial x-ray diffraction studies of CBDC [12] and PhMDA [13] were performed only at room temperature for CBDC and at T =111 K for PhMDA. It was only recently that new measurements were extended to low temperature for CBDC and to room temperature for PhMDA, [14] showing that both compounds are ferroelectric with Curie temperatures above 400 and 363 K respectively.…”

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confidence: 99%

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Polar distortions in hydrogen-bonded organic ferroelectrics

et al. 2011

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Although ferroelectric compounds containing hydrogen bonds were among the first to be discovered, organic ferroelectrics are relatively rare. The discovery of high polarization at room temperature in croconic acid [Nature 463, 789 (2010)] has led to a renewed interest in organic ferroelectrics. We present an ab-initio study of two ferroelectric organic molecular crystals, 1-cyclobutene-1,2-dicarboxylic acid (CBDC) and 2-phenylmalondialdehyde (PhMDA). By using a distortion-mode analysis we shed light on the microscopic mechanisms contributing to the polarization, which we find to be as large as 14.3 and 7.0 µC/cm 2 for CBDC and PhMDA respectively. These results suggest that it may be fruitful to search among known but poorly characterized organic compounds for organic ferroelectrics with enhanced polar properties suitable for device applications.

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Polar distortions in hydrogen-bonded organic ferroelectrics

et al. 2011

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“…The moderate hydrogen bond is mainly the electrostatic interaction, this kind of hydrogen bond allow the movement of the proton along the hydrogen bond to realize polarization reversal, also can introduce a high polarization. Recently, some organic ferroelectrics 25 of chains via moderate hydrogen bonds, such as 2-phenylmalondialdehyde (PhMDA) 26 and cyclobutene-1,2-dicarboxylic acid (CBDC), 27 are discovered. [24][25][26] The polarization and the polarization reversal of these organic ferroelectrics are also from the contribution of the hydrogen bonds.…”

Section: B Polarization Reversalmentioning

confidence: 99%

“…Recently, some organic ferroelectrics 25 of chains via moderate hydrogen bonds, such as 2-phenylmalondialdehyde (PhMDA) 26 and cyclobutene-1,2-dicarboxylic acid (CBDC), 27 are discovered. [24][25][26] The polarization and the polarization reversal of these organic ferroelectrics are also from the contribution of the hydrogen bonds. 12 Moderate hydrogen bond is a very important clue to find new organic ferroelectrics.…”

Section: B Polarization Reversalmentioning

confidence: 99%

Ferroelectric mechanism of croconic acid: A first-principles and Monte Carlo study

Cai

Luo

Zhu

et al. 2013

The Journal of Chemical Physics

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The ferroelectric mechanism of croconic acid in terms of the electronic structure and the molecular structure was studied by first principles using the density functional theory with the generalized gradient approximation. The spontaneous polarization (Ps) was simulated by the Berry phase method. It is found that the large polarization originates from charge transfer due to the strong "push-pull" effect of electron-releasing and -withdrawing groups along the hydrogen bond. According to the characteristics of polarization of croconic acid, we constructed a one-dimensional ferroelectric Hamiltonian model to describe the ferroelectric properties of croconic acid. Based on the Hamiltonian model, the thermal properties of the ferroelectricity of croconic acid were studied by Monte Carlo method. The simulated Curie temperature is 756 K, and the spontaneous polarization keeps well temperature range stability up to 400 K. These results are in good agreement with the experimental data.

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“…OH 0 Keto-enol tautomerism is a well known feature in fl-diketone derivatives and their molecular and crystal structures have been investigated (Engebretson & Rundle, 1964;Semmingsen, 1977). The C (8) 7) dihedral angles, the four C atoms and 0(3) are inferred to be almost on the same plane.…”

Section: Commentmentioning

confidence: 99%