<i>p</i>-Phenylenediacrylic acid dimethyl ester (<i>p</i>PDAMe), a photopolymerizable crystal

Ueno, Kenzo; Nakanishi, Hiroshi; Hasegawa, Miki; Sasada, Yoshio

doi:10.1107/s056774087800730x

Cited by 23 publications

(9 citation statements)

References 6 publications

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“…This CdO‚‚‚π interaction between these two groups in 1 is shown pictorially in Figure 5. 11,14 Although similar interactions between the carboxylate carbonyl group and the phenyl ring have been observed before, [11][12][13][14] this was documented by Addadi and Lahav for the first time in 1979. 11 Later, Moorthy et al interpreted the solid state photochemical reactivity of some coumarin derivatives in terms of CdO‚‚‚π interactions.…”

supporting

confidence: 56%

“…A close examination of the interactions between the carboxylate group and the phenyl ring edge in 1 reveals that they are aligned almost parallel and separated by 3.352 Å (C9A···C5) in 1 and 3.650 Å (C9A···C5) in 2 . This CO···π interaction between these two groups in 1 is shown pictorially in Figure . , Although similar interactions between the carboxylate carbonyl group and the phenyl ring have been observed before, − this was documented by Addadi and Lahav for the first time in 1979 . Later, Moorthy et al interpreted the solid state photochemical reactivity of some coumarin derivatives in terms of CO···π interactions .…”

mentioning

confidence: 81%

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Influence of the CO···π Interaction on the Thermal Dehydration Behavior of [Cu₂(sgly)₂(H₂O)]·1H₂O

Yang

Ranford

et al. 2004

Crystal Growth & Design

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The hydrogen-bonding pattern present in [Cu 2 (sgly) 2 (H 2 O)]‚H 2 O [1; H 2 sgly ) N-(2-hydroxybenzyl)glycine] has been found to be very similar to that observed in [Cu 2 (sala) 2 (H 2 O)] (2), which undergoes solid state transformation from a hydrogen-bonded one-dimensional helical coordination polymeric structure to a three-dimensional (3D) coordination polymeric network structure with chiral channels, after losing all of the water molecules below 110 °C. However, 1 fails to undergo such a transformation when dehydrated thermally. Furthermore, the intermolecular hydrogen bonds in 1 are weaker than those found in 2. A detailed crystal structure analysis of 1 reveals that the presence of the CdO‚‚‚π intermolecular interaction between a carboxylate carbonyl group and a phenyl ring appears to be responsible for the weakening of hydrogen bonds, thermal dehydration behavior, preventing the formation of new Cu-O bonds and, hence, the 3D coordination polymeric network structure.

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supporting

confidence: 56%

mentioning

confidence: 81%

Influence of the CO···π Interaction on the Thermal Dehydration Behavior of [Cu₂(sgly)₂(H₂O)]·1H₂O

Yang

Ranford

et al. 2004

Crystal Growth & Design

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“…An electrostatic 'the crystal packing of 2 interaction has been supposed to operate between the electron deficient phenyl group and the electron rich oxygen atom of the carbonyl group. 21 In the light of the above reports, the hypothesis that the derivatives S 9 effectively employ, in the centrosymmetric arrangement, the C=O 7c interaction, besides the potential n n interactions appears reasonable. The efficient formation of centrosymmetric anti-HT photodimers from all the derivatives clearly indicates a-type packing mode.…”

Section: Resultsmentioning

confidence: 92%

Studies in crystal engineering: structure–reactivity correlations of substituted styrylcoumarins and related systems

Moorthy¹,

Samant²,

Venkatesan³

1994

J. Chem. Soc., Perkin Trans. 2

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The solid state photochemical behaviour of 7hydroxy-4-styrylcoumarin 1 and several of its derivatives and analogues has been investigated. All the compounds with the exception of 7-methoxy-4-styrylcoumarin 2 are photolabile and yield anti-HT dimers. It has been observed that chloro substitution in the systems studied does not lead to the expected P-packing mode. The photobehaviour of I and 2 has been correlated with their crystal structures. Reasons for x-packing have been examined. The systematics in the arrangement of the carbonyl group and phenyl group of the close neighbours in the crystals of 1 , 2 and a few other cases are presented.Ever since the geometrical criteria for facile [2 + 21 photocycloaddition in the solid state were established, extensive studies have been pursued to preorganize the reactants in the solid state in a predetermined fashion. However, interest has largely been focused on rationalization of the reactivity of pstructures in which the reactive partners are related by a mirror symmetry or design t h e r e ~f . ~-~ An analysis of N-packed structures characterized by a molecular organization with adjacent molecules related by a centre-of-symmetry with centreto-centre to distance of ca. 4.0 8, has not been a subject of detailed examination.Photodimerization of coumarins in the solid state have been widely investigated in our lab~ratories.~ More often than not, the photodimer obtained is mirror symmetric, implying the 13-type packing of the precursor monomers. It was observed that 4-styrylcoumarin endowed with two potentially reactive double bonds crystallizes as photoreactive N-packed dimorphs. It was considered worthwhile examining the packing modes and photobehaviour of a few derivatives and analogues of 4styrylcoumarin. We report herein the correlation between crystal structures and the photobehaviour of 7-hydroxy-4styrylcoumarin 1 and 7-methoxy-4-styrylcoumarin 2 and the photochemical results of several of their analogues and derivatives.Paper 4/00428K

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“…The layers are further extended by C-HÁ Á ÁO hydrogen bonds to form a 3D framework. It must be remarked that an unusual contact between a carboxylate C@O group of the HL and the p system of the pyridine ring is observed, which is responsible for strengthening of the 3D assem- , which is similar to that in the compounds reported recently [18][19][20][21][22][23]. A closer inspection of the structure reveals that the C-HÁ Á Áp and C-HÁ Á ÁO interactions provide an extra source of stability (Fig.…”

mentioning

confidence: 72%

Synthesis, crystal structure and properties of Zn(II) and Cd(II) complexes with 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)nicotinic acid ligand

Yin

et al. 2010

Inorganic Chemistry Communications

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p-Phenylenediacrylic acid dimethyl ester (pPDAMe), a photopolymerizable crystal

Cited by 23 publications

References 6 publications

Influence of the CO···π Interaction on the Thermal Dehydration Behavior of [Cu₂(sgly)₂(H₂O)]·1H₂O

Influence of the CO···π Interaction on the Thermal Dehydration Behavior of [Cu₂(sgly)₂(H₂O)]·1H₂O

Studies in crystal engineering: structure–reactivity correlations of substituted styrylcoumarins and related systems

Synthesis, crystal structure and properties of Zn(II) and Cd(II) complexes with 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)nicotinic acid ligand

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p-Phenylenediacrylic acid dimethyl ester (pPDAMe), a photopolymerizable crystal

Cited by 23 publications

References 6 publications

Influence of the CO···π Interaction on the Thermal Dehydration Behavior of [Cu2(sgly)2(H2O)]·1H2O

Influence of the CO···π Interaction on the Thermal Dehydration Behavior of [Cu2(sgly)2(H2O)]·1H2O

Studies in crystal engineering: structure–reactivity correlations of substituted styrylcoumarins and related systems

Synthesis, crystal structure and properties of Zn(II) and Cd(II) complexes with 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)nicotinic acid ligand

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Influence of the CO···π Interaction on the Thermal Dehydration Behavior of [Cu₂(sgly)₂(H₂O)]·1H₂O

Influence of the CO···π Interaction on the Thermal Dehydration Behavior of [Cu₂(sgly)₂(H₂O)]·1H₂O