Self-assembly of taper-shaped monoesters of oligo(ethylene oxide) with 3,4,5-tris(p-dodecyloxybenzyloxy)benzoic acid and of their polymethacrylates into tubular supramolecular architectures displaying a columnar mesophase

Percéc, Virgil; Heck, J.; Tomazos, Dimitris; Falkenberg, Frederick; Blackwell, Helen E.; Ungar, Goran

doi:10.1039/p19930002799

Cited by 192 publications

(168 citation statements)

References 20 publications

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“…The PXRD analysis revealed that 1O was converted to 1O Li (T iso ¼ 120°C) by forming chelation complexes in the TEG moieties ( Supplementary Fig. 7) 35,36 . The interlayer distance was ARTICLE extended from 34.2 Å in 1O to 60.1 Å in 1O Li ; this change could be ascribed to the cancellation of the molecular tilt owing to the loss of the interdigitation of the TEG moieties upon chelation with the salt (Fig.…”

Section: Molecular Designmentioning

confidence: 99%

Design amphiphilic dipolar π-systems for stimuli-responsive luminescent materials using metastable states

et al. 2014

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p-Conjugated compounds that exhibit tunable luminescence in the solid state under external mechanical stimuli have potential applications in sensors and imaging devices. However, no rational designs have been proposed that impart these mechano-responsive luminescent properties to p-conjugated compounds. Here we demonstrate a strategy for mechanoresponsive luminescent materials by imparting amphiphilic and dipolar characteristics to a luminescent p-conjugated system. The oligo(p-phenylenevinylene) luminophore with a didodecylamino group at one end and a tri(ethylene glycol) ester group at the other end yields segregated solid structures by separately aggregating its hydrophobic and hydrophilic moieties. The segregated structures force the molecules to align in the same direction, thereby generating a conflict between the side-chain aggregation and dipolar stabilization of the p-system. Consequently, these metastable solid structures can be transformed through mechanical stimulation to a more stable structure, from a p-p stacked aggregate to a liquid crystal and further to a crystalline phase with variable luminescence.

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Section: Molecular Designmentioning

confidence: 99%

Design amphiphilic dipolar π-systems for stimuli-responsive luminescent materials using metastable states

et al. 2014

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“…Figures 13d and 14 illustrate the proposed different mehanisms of the self-assembly of cylindrically shaped tubular suprmoleclar architectures presented in this paper [18,20,22]. Figure 13d illustrates the semicolumns of n+ t-AG-DA2 which form cylinders that pack into a hexagonal lattice generating a ODh mesophase.…”

Section: Endo-receptors Based On H-bondin"mentioning

confidence: 89%

“…All compounds form an enantiotropic Oh mesophase which was characterized by a combination of x-ray scattering, thermal optical polarized microscopy, and DSC experiments. 18 The mechanism of formation and stabilization of the self-assembled supramolecular columns is similar for both 12-ABG. nEO-OH and 12-ABG-nEO-PMA but provides access to a systematic investigation of the difference between the two systems as n is varied.…”

Section: Fiue7mentioning

confidence: 92%

“…Molecular models were constructed for all compounds to provide explanations for these observations in phase behavior and column diameter [18,19]. Figure 7c illustrates a model of a cross-section of the cylinder formed by 12-ABG-nEO-OH with the alkyl tails and the flexible oligooxyethylene spacer melted so that the radius of the model is equivalent to the value determined by x-ray scattering experiments.…”

Section: Fiue7mentioning

confidence: 99%

“…The effect of the LiOTf on the phase behavior of the resulted complex is shown in Figure 8 for the compounds 12.ABG-nEO-OH [18,19] with n = 1 to 4 and for the model compound 12-ABG-3EO-OCH 3 [18]. Figure 8a displays representative DSC traces of 12-ABG-3EO-OH with increasing the amount of LiOTf.…”

Section: Fiue7mentioning

confidence: 99%

See 2 more Smart Citations

Molecular Recognition Directed Self-Assembly of Supramolecular Liquid Crystals

Percéc

Heck

Johansson

et al. 1994

Molecular Crystals and Liquid Crystals Science and Technology.

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A second columnar liquid crystalline phase formed by polymers with highly tapered side chains

Чвалун

Blackwell²,

Cho

et al. 1999

Acta Polym.

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Previous work has shown that polymethacrylates with highly tapered side groups, such as poly{2-{2-[2-(2-methacryloyloxyethoxy)-ethoxy]ethoxy}ethyl-3,4,5-tris-(p-dodecyloxy-benzyloxy)benzoate} (H12-ABG-4EO-PMA), form columnar hexagonal (Col h , previously designated v h ) liquid crystalline structures. The small angle X-ray data for drawn fibers of H12-ABG-4EO-PMA, and also those of its hydroxy-terminated monomer precursor and decyloxy-homologue, contain several weak equatorial Bragg reflections in addition to those characteristic of the Col h phase. The intensities of these extra reflections decline progressively on heating and disappear before the temperature of the Col h -to-isotropic transition is reached. It is proposed that the as-drawn fibers contain a second phase, which is probably a columnar liquid crystalline structure in view of the decreases in the observed d-spacings with increasing temperature. The additional reflections are indexed by a two dimensional monoclinic lattice, which probably contains columns with elliptical cross-section. The lower symmetry is consistent with the formation of a tilted columnar phase analogous to those formed by certain low molecular weight discotic materials.

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Self-assembly of taper-shaped monoesters of oligo(ethylene oxide) with 3,4,5-tris(p-dodecyloxybenzyloxy)benzoic acid and of their polymethacrylates into tubular supramolecular architectures displaying a columnar mesophase

Cited by 192 publications

References 20 publications

Design amphiphilic dipolar π-systems for stimuli-responsive luminescent materials using metastable states

Design amphiphilic dipolar π-systems for stimuli-responsive luminescent materials using metastable states

Molecular Recognition Directed Self-Assembly of Supramolecular Liquid Crystals

A second columnar liquid crystalline phase formed by polymers with highly tapered side chains

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