The influence of ultrasound on porphyrin-based metallogel formation: efficient control of H- and J-type aggregations

Cho, Youngje; Lee, Ji Ha; Jaworski, Justyn; Park, Sunhong; Lee, Shim Sung; Jung, Jong Hwa

doi:10.1039/c1nj20781d

Cited by 24 publications

(24 citation statements)

References 24 publications

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“…34 The Fe-C bond lengths of the ferrocene groups and Pd-N bond lengths for the calculated structures were comparable to X-ray determined values (see ESI). 35,36 The large bulky ferrocene groups in PdTFcP distort the porphyrin ring which is evident from the calculated dihedral angles. Minimised structures were also calculated for the radical anion (doublet state) and dianion (singlet state) species.…”

Section: Computational and Mechanistic Considerationsmentioning

confidence: 94%

The ferrocene effect: enhanced electrocatalytic hydrogen production using meso-tetraferrocenyl porphyrin palladium(ii) and copper(ii) complexes

et al. 2015

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Copper(ii) and palladium(ii) meso-tetraferrocenylporphyrins ( and ) were employed as catalysts for electrochemical proton reduction in DMF using trifluoroacetic acid (TFA) or triethylamine hydrochloride (TEAHCl) as acids. Gas analysis under electrocatalytic conditions at a glassy carbon working electrode confirmed the product as H2. showed catalytic behavior for both TFA and TEAHCl, whereas only TFA worked for . The performance of the two compounds for electrocatalytic hydrogen generation was compared to the analogous copper(ii) and palladium(ii) meso-tetraphenylporphyrins ( and ) under identical conditions. The presence of the ferrocence groups on the porphyrin favourably shift the overpotential to a less negative value by around 200 mV and increases the catalytic rate of hydrogen production in DMF/TFA by an order of magnitude to 6 × 10(3) s(-1). Moreover, while is fully inactive in a DMF/TEAHCl mixture, the ferrocene subunits activate the catalyst. Spectroelectrochemistry experiments and DFT calculations were consistent with a catalytic process proceeding via the phlorin anion.

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Section: Computational and Mechanistic Considerationsmentioning

confidence: 94%

The ferrocene effect: enhanced electrocatalytic hydrogen production using meso-tetraferrocenyl porphyrin palladium(ii) and copper(ii) complexes

et al. 2015

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“…Sonogelation of quinacridone derivatives functionalized with urea12d or cholesterol12e,f moieties have been demonstrated by Zhang, Wang, and co‐workers. Moreover, Jung et al., have observed that sonication could modulate the aggregation as well as gelation properties of a porphyrin–palladium(II) complex 12g…”

Section: Introductionmentioning

confidence: 99%

Ultrasound Stimulated Nucleation and Growth of a Dye Assembly into Extended Gel Nanostructures

Malicka

Sandeep

Monti

et al. 2013

Chemistry A European J

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A squaraine dye functionalized with a bulky trialkoxy phenyl moiety through a flexible diamide linkage (GA-SQ) capable of undergoing self-assembly has been synthesized and fully characterized. Rapid cooling of a hot solution of GA-SQ to 0 °C results in self-assembled precipitates consisting of two types of nanostructures, rings and ill-defined short fibers. The application of ultrasound modifies the conditions for the supersaturation-mediated nucleation, generating only one kind of nuclei and prompting the formation of crystalline fibrous structures, inducing gelation of solvent molecules. The unique self-assembling behavior of GA-SQ under ultrasound stimulus has been investigated in detail by using absorption, emission, FT-IR, XRD, SEM, AFM and TEM techniques. These studies reveal a nucleation growth mechanism of the self-assembled material, an aspect rarely scrutinized in the area of sonication-induced gelation. Furthermore, in order to probe the effects of nanoscale substrates on the sonication-induced self-assembly, a minuscule amount of single-walled carbon nanotubes was added, which leads to acceleration of the self-assembly through a heterogeneous nucleation process that ultimately affords a supramolecular gel with nanotape-like morphology. This study demonstrates that self-assembly of functional dyes can be judiciously manipulated by an external stimulus and can be further controlled by the addition of carbon nanotubes.

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“…For example, Ajayaghosh and Praveen found that OPV derivatives terminated with one or more hydroxyl groups give gels with Jaggregate structures, whereas derivatives terminated with cholesteryl esters produce H-aggregate materials. 226 The balance between H-and J-aggregation may be influenced by environmental changes, such as exposure to heating or sonication, 227 variation in the solvent [228][229][230] or addition of a strongly binding additive. 231 According to Würthner et al, 210 the synthetic route is particularly important when aggregation is governed by non-directional van der Waals interactions, as in the stacking of pseudoisocyanine dyes.…”

Section: Optical Responsesmentioning

confidence: 99%

“…15). 227 The reverse process, conversion from J-to H-aggregates, can be induced through subsequent sonication of the sol. Switching between phases is associated with changes in both colour and fluorescence: the thermally generated metallogel is green and exhibits the non-emissivity typical of H-aggregates, whereas the J-aggregate is red and more strongly fluorescent than both the original gel and the dissolved monomer.…”

Section: Optical Responsesmentioning

confidence: 99%

Gels with sense: supramolecular materials that respond to heat, light and sound

2016

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. (2016) 'Gels with sense : supramolecular materials that respond to heat, light and sound.', Chemical society reviews., 45 (23). pp. 6546-6596. Further information on publisher's website:https://doi.org/10.1039/C6CS00435KPublisher's copyright statement:Additional information: Use policyThe full-text may be used and/or reproduced, and given to third parties in any format or medium, without prior permission or charge, for personal research or study, educational, or not-for-prot purposes provided that:• a full bibliographic reference is made to the original source • a link is made to the metadata record in DRO • the full-text is not changed in any way The full-text must not be sold in any format or medium without the formal permission of the copyright holders.Please consult the full DRO policy for further details. Advances in the field of supramolecular chemistry have made it possible, in many situations, to reliably engineer soft materials to address a specific technological problem. Particularly exciting are "smart" gels that undergo reversible physical changes on exposure to remote, non-invasive environmental stimuli. This review explores the development of gels which are transformed by heat, light and ultrasound, as well as other mechanical inputs, applied voltages and magnetic fields. Focusing on small-molecule gelators, but with reference to organic polymers and metal-organic systems, we examine how the structures of gelator assemblies influence the physical and chemical mechanisms leading to thermo-, photo-and mechano-switchable behaviour. In addition, we evaluate how the unique and versatile properties of smart materials may be exploited in a wide range of applications, including catalysis, crystal growth, ion sensing, drug delivery, data storage and biomaterial replacement.

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The influence of ultrasound on porphyrin-based metallogel formation: efficient control of H- and J-type aggregations

Cited by 24 publications

References 24 publications

The ferrocene effect: enhanced electrocatalytic hydrogen production using meso-tetraferrocenyl porphyrin palladium(ii) and copper(ii) complexes

The ferrocene effect: enhanced electrocatalytic hydrogen production using meso-tetraferrocenyl porphyrin palladium(ii) and copper(ii) complexes

Ultrasound Stimulated Nucleation and Growth of a Dye Assembly into Extended Gel Nanostructures

Gels with sense: supramolecular materials that respond to heat, light and sound

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