Studies of structures and properties of polymeric systems containing bis-(hydroxy-arylidene)alkanones as NLO-active chromophores

Yakimansky, Alexander V.; Теньковцев, А. В.; Dudkina, M. M.; Voigt‐Martin, I. G.; Kolb, Ute; Lukoshkin, V. A.; Böhme, Frank

doi:10.1016/s0022-3093(01)01215-7

Cited by 10 publications

(7 citation statements)

References 25 publications

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“…With respect to 3rd order NLO activity the opposite behavior was found as described earlier [12][13][14][15].…”

Section: Discussionmentioning

confidence: 47%

“…We have found [12][13][14][15] that complexes formed by noncovalent interactions between organic dyes and a suitable polymeric carrier exhibit nonlinear optical properties with an efficiency comparable to the response of polythiophenes or polyphenylenevinylenes. This new approach to polymeric NLO active materials seems to be very promising in comparison with the above mentioned alternatives.…”

Section: Introductionmentioning

confidence: 99%

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A spectroscopic study on the dissociation behavior of 4-hydroxybenzylideneacetone type NLO chromophores in the presence of sodium hydroxide

et al. 2006

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“…With respect to 3rd order NLO activity the opposite behavior was found as described earlier [12][13][14][15].…”

Section: Discussionmentioning

confidence: 47%

Section: Introductionmentioning

confidence: 99%

A spectroscopic study on the dissociation behavior of 4-hydroxybenzylideneacetone type NLO chromophores in the presence of sodium hydroxide

et al. 2006

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“…These compounds are used in the construction of different polymers (Yakimansky et al, 2002;Aly et al, 2003), and in the design of crystals with nonlinear optical (Kishore & Kishore, 1993;Kawamata et al, 1995Kawamata et al, , 1996Sarkisov et al, 2005) and fluorescent (Nesterov et al, 2003(Nesterov et al, , 2008 properties. Furthermore, it is well known that they possess a variety of biological activities, such as antiviral (ElSubbagh et al, 2000), antibacterial (Lyrand et al, 1999;Amal Raj et al, 2003) and antiphlogistic activity (Rovnyak et al, 1982).…”

Section: Commentmentioning

confidence: 99%

From small structural modifications to adjustment of structurally dependent properties: 1-methyl-3,5-bis[(E)-2-thienylidene]-4-piperidone and 3,5-bis[(E)-5-bromo-2-thienylidene]-1-methyl-4-piperidone

et al. 2009

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The molecules of the title compounds, C 16 H 15 NOS 2 , (I), and C 16 H 13 Br 2 NOS 2 , (II), are E,E-isomers and consist of an extensive conjugated system, which determines their molecular geometries. Compound (I) crystallizes in the monoclinic space group P2 1 /c. It has one thiophene ring disordered over two positions, with a minor component contribution of 0.100 (3). Compound (II) crystallizes in the noncentrosymmetric orthorhombic space group Pca2 1 with two independent molecules in the unit cell. These molecules are related by a noncrystallographic pseudo-inversion center and possess very similar geometries. The crystal packings of (I) and (II) have a topologically common structural motif, viz. stacks along the b axis, in which the molecules are bound by weak C-HÁ Á ÁO hydrogen bonds. The noncentrosymmetric packing of (II) is governed by attractive intermolecular BrÁ Á ÁBr and BrÁ Á ÁN interactions, which are also responsible for the very high density of (II) (1.861 Mg m À3). CommentCross-conjugated dienones of the bis-arylidenecycloalkanone series and related piperidones have recently attracted considerable attention. These compounds are used in the construction of different polymers (Yakimansky et al., 2002;Aly et al., 2003), and in the design of crystals with nonlinear optical (Kishore & Kishore, 1993;Kawamata et al., 1995Kawamata et al., , 1996Sarkisov et al., 2005) and fluorescent (Nesterov et al., 2003(Nesterov et al., , 2008 properties. Furthermore, it is well known that they possess a variety of biological activities, such as antiviral (ElSubbagh et al., 2000), antibacterial (Lyrand et al., 1999;Amal Raj et al., 2003) and antiphlogistic activity (Rovnyak et al., 1982).Recently, instead of aryl substituents, the use of heterocyclic ligands was suggested, as these are able to bind important metal cations to form diverse coordination associates One purpose of our investigation was to analyze the influence of small structural modifications of the molecules on their structurally dependent properties. It should be noted that these compounds are potential antitumor (anticancer) agents (Dimmock et al., 1992(Dimmock et al., , 1994(Dimmock et al., , 2001, and even small differences in the structures may cause significant changes in their biological activity.Compound (I) crystallizes in the monoclinic space group P2 1 /c. One thiophene ring is disordered over two positions related by a 180 rotation about the C6-C7 bond. The minor component contribution refined to 0.100 (3) (Fig. 1). The molecular structure of (I), showing the atom-numbering scheme. The alternative position of the disordered thiophene ring is drawn with open lines. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.

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“…We reported about aliphatic polyamidines which proved to be strong organic bases. In mixtures with different phenolic group containing chromophores, the formation of ionic complexes was observed. − Because of deprotonation, the chromophores exhibited a bathochromic shift of their longest wavelength absorption band by more than 100 nm. Additionally, third-order nonlinear optical activity was evidenced on solution-cast films.…”

Section: Introductionmentioning

confidence: 99%

Ionic Interactions in Blends of Polyamidines and Proton Donor Terminated Poly(alkylene ether)s

et al. 2005

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4-(Iminomethyl)phenol and 4-(iminomethyl)benzoic acid terminated aliphatic polyethers were obtained by conversion of Jeffamines with respective aromatic aldehydes. Mixtures of these polymers with polyamidines showed improved compatibility or even complete miscibility because of ionic complexes formed between the end groups of the modified polyethers and the basic amidine groups. Depending on composition and molecular weight of the components, blends with two or one glass transitions were obtained. In the case of 4-(iminomethyl)phenol terminated polyethers, deprotonation of the end groups resulted in a distinct change of the UV/vis absorption spectrum. This spectral alteration is discussed with respect to quantification of interactions in polymer blends.

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Studies of structures and properties of polymeric systems containing bis-(hydroxy-arylidene)alkanones as NLO-active chromophores

Cited by 10 publications

References 25 publications

A spectroscopic study on the dissociation behavior of 4-hydroxybenzylideneacetone type NLO chromophores in the presence of sodium hydroxide

A spectroscopic study on the dissociation behavior of 4-hydroxybenzylideneacetone type NLO chromophores in the presence of sodium hydroxide

From small structural modifications to adjustment of structurally dependent properties: 1-methyl-3,5-bis[(E)-2-thienylidene]-4-piperidone and 3,5-bis[(E)-5-bromo-2-thienylidene]-1-methyl-4-piperidone

Ionic Interactions in Blends of Polyamidines and Proton Donor Terminated Poly(alkylene ether)s

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