Self-assembling properties of non-ionic tetraphenylporphyrins and discotic phthalocyanines carrying oligo(ethylene oxide) alkyl or alkoxy units

Kroon, J.M.; Koehorst, R.B.M.; Dijk, M. van; Sanders, Georgine M.; Sudhölter, Ernst J. R.

doi:10.1039/a605328i

Cited by 89 publications

(48 citation statements)

References 39 publications

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“…Phthalocyanine 1a is synthesized as reported earlier [4,20]. The 1-bromo-oligo(ethylene oxide)alkanes 2b and 2c are prepared by dissolving sodium in di-and monoethylene glycol monomethyl ether, respectively, followed by addition of 1,6-dibromohexane.…”

Section: Synthesismentioning

confidence: 99%

“…In many such applications, control over the morphology of the liquid crystal is of interest. Following the discovery of the mesomorphism of porphyrins [2], we became interested in the study of the effects of oligo(ethylene oxide) substituents on the liquid crystalline behavior of porphyrins [3,4]. Apart from the observation that tetraphenylporphyrins carrying oligo(ethylene oxide) groups belong to the rather small class of porphyrins with liquid crystalline phases, the presence of ethylene oxide moieties allows for the solubilization of salts.…”

Section: Introductionmentioning

confidence: 99%

“…Pc molecules with oligo(ethylene oxide) groups directly attached to the aromatic macrocycle display the following interesting properties: 1) formation of hexagonally ordered columnar mesophases such as depicted in Fig. 1 [4], which are of particular interest in photoelectronic device development [9,10], 2) effective complexation to Li cations [11,12] and 3) significantly lowered isotropization temperature with respect to reference compounds with linear alkoxy chains [4]. Analogously, Pcʼs substituted with crown ethers have been studied extensively [13], specifically with regard to their complexation behavior and applicability for electronic and ionic conduction [14][15][16][17].…”

Section: Introductionmentioning

confidence: 99%

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Phthalocyanines with eight oligo(ethylene oxide) alkoxy units: thermotropic phase behavior, aggregate formation and ion complexation with redox-active ions

Piet

Verheij

Zuilhof

2003

J. Porphyrins Phthalocyanines

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The thermotropic phase behavior of phthalocyanines (Pcʼs) with eight oligo(ethylene oxide) alkoxy side chains has been investigated. An increase in the number of ethylene oxide units results in a decrease in the solid-to-mesophase and isotropization temperatures. The investigated compounds display a discotic hexagonally ordered (D ho ) mesophase. The solubilization of LiI/I 2 into the polar side chains of the Pcʼs has been studied both in solution and in spin-coated films, and the effect on the aggregate formation is discussed. At higher temperatures, the Pc -LiI/I 2 complex is not stable and small crystallites are formed. The dark direct current conductivity of these films is reported as a function of LiI/I 2 concentration in the polar side groups of the Pcʼs. The observed decrease in conductivity with increasing salt concentration is related to the morphology of the material.

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Section: Synthesismentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Phthalocyanines with eight oligo(ethylene oxide) alkoxy units: thermotropic phase behavior, aggregate formation and ion complexation with redox-active ions

Piet

Verheij

Zuilhof

2003

J. Porphyrins Phthalocyanines

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“…Interestingly, all showed a strong tendency to align homeotropically on the glass substrate, which may be potentially utilized for pattern applications on distinctly chemically modified surfaces ( Figure 22a-c). 61,62 Unlike 27 and 28, the crystalline phase of 29 was experimentally accessible. Interestingly, the crystalline phase maintained the two-dimensional hexagonal columnar structure similar to its LC phase, as confirmed by the small-angle X-ray scattering data (Figure 22d).…”

Section: Poly(benzyl Ether) Dendron-based Discotic Lc Materials Usingmentioning

confidence: 99%

Spontaneous bulk organization of molecular assemblers based on aliphatic polyether and/or poly(benzyl ether) dendrons

Cho

2012

Polym J

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This paper reviews our recent research with regard to bulk self-assemblers based on well-defined branched building blocks. Branched molecules/polymers have been known to show different physical properties from conventional linear-shaped polymers. As well as thermal and solution properties, structural modification into branched building blocks also has a significant influence on self-assembling behavior in the bulk states, including solid and liquid crystalline (LC) phases. As a branched component, dendrons/dendrimers with well-defined structures can be ideal candidates for the construction of advanced self-assemblers. Recently, we worked on new assembling systems such as dendron-coils, block codendrimers and discotic LC molecules. In the design, we used aliphatic polyether dendrons in most cases and poly(benzyl ether) dendrons in part. Their bulk assembling and thermal properties were found to be distinct from conventional linear block copolymers and they were dependent upon their chain architectures. To self-assemble into ordered nanostructures, the hybrid assembers were designed to have incompatible blocks, for example, hydrophilic and hydrophobic parts. Furthermore, in some cases an ionic complexation was carried out to maximize the immiscibility between the two different blocks. This review describes the molecular manipulations to engineer the nanoassemblies in bulk and also the ionic transportation properties depending on the assembling morphology.

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“…According to the molecular (in wavenumber, ∆ν) for an aggregate consisting of N exciton model proposed by Kasha, [10Ϫ12] the blue shift from monomers with respect to the monomer absorption is the monomer band is indicative of linear chromophore ag-given by [16] gregation with their transition moments parallel to each other and ordered perpendicular to the stacking direction (so-called H aggregates). [13] The wavelength shift depends, among others, on the mutual orientations and distance, and on the aggregation number of the chromophores. The obin which µ is the magnitude of the transition dipole moment, r is the centre-to-centre distance between the dipoles served blue shift of the fluoroazobenzoxy units results from the parallel aggregation of the fluoroazobenzoxy chromo-and α is the angle between the chromophore long axes and the chromophore centre-to-centre line.…”

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confidence: 99%

Interactions between Chromophore-Labelled Ammonium Surfactants and Hydrophobically Modified Polyelectrolytes

Nieuwkerk¹,

Kan²,

Koudijs³

et al. 1999

Eur. J. Org. Chem.

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The interaction of poly(maleic acid‐co‐alkyl vinyl ether)s and poly(sulfonylethyl maleic acid monoamide‐co‐alkyl vinyl ether)s with and without (cyanobiphenylyl)oxy chromophores with N‐[ω‐(substituted azobenzoxy)alkyl]‐N,N‐dimethyl‐N‐hydroxyethylammonium bromide surfactants has been studied by UV spectroscopy. The azobenzene unit is functionalized at the 4′‐position with a cyano or fluoro substituent and is connected to the surfactant headgroup via a decyl or dodecyl spacer. Upon addition of surfactants to poly(maleic acid‐co‐butyl vinyl ether) the absorption maxima (λmax) of the azobenzene chromophores immediately show their maximum blue shift. This indicates cooperative binding of surfactant to this polymer, and the formation of micelle‐like aggregates surrounded by polyelectrolyte is assumed. Upon addition of the surfactants to the other polyelectrolytes λmax values of the azobenzoxy chromophores gradually shift to lower values indicating a lower cooperativity of surfactant binding. This is attributed to the formation of microdomains by the polyelectrolytes themselves. For these systems the formation of mixed micelles is assumed. The compactness of the microdomains of the maleic acid copolymers is influenced by the pH and binding with surfactants is also influenced by pH. The sulfonylethyl maleic acid monoamide copolymers show no pH dependence in binding above neutral pH. For these polyelectrolytes the cooperativity also becomes less with a longer spacer between backbone and chromophore. Upon elongation of the surfactant spacer or changing the end group from a cyano to the more hydrophobic fluoro substituent a lower λmaxis observed for the chromophores upon initial binding to the polyelectrolytes indicating more cooperative binding. When surfactants and polyelectrolytes are both labelled with chromophores, binding proceeds noncooperatively and the formation of mixed micelles is assumed.

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Self-assembling properties of non-ionic tetraphenylporphyrins and discotic phthalocyanines carrying oligo(ethylene oxide) alkyl or alkoxy units

Cited by 89 publications

References 39 publications

Phthalocyanines with eight oligo(ethylene oxide) alkoxy units: thermotropic phase behavior, aggregate formation and ion complexation with redox-active ions

Phthalocyanines with eight oligo(ethylene oxide) alkoxy units: thermotropic phase behavior, aggregate formation and ion complexation with redox-active ions

Spontaneous bulk organization of molecular assemblers based on aliphatic polyether and/or poly(benzyl ether) dendrons

Interactions between Chromophore-Labelled Ammonium Surfactants and Hydrophobically Modified Polyelectrolytes

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