Chiral Perylene Materials by Ionic Self-Assembly

Echue, Geraldine; Hamley, Ian W.; Lloyd‐Jones, Guy C.; Faul, Charl F. J.

doi:10.1021/acs.langmuir.6b02201

Cited by 23 publications

(62 citation statements)

References 61 publications

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“…Supramolecular soft materials − consisting of organic π-conjugated molecules − are attracting enormous interest due to their successful applications in organic electronics. The interesting photophysical properties, high π-acidity, and redox behavior of naphthalene diimide (NDI) make it an excellent candidate for various applications. − Moreover, this moiety offers better solubility, and it is relatively easier to synthesize compared to its higher analogues such as perylene, terrylene, and quaterrylenes.…”

Section: Introductionmentioning

confidence: 99%

Luminescent Naphthalene Diimide-Based Peptide in Aqueous Medium and in Solid State: Rewritable Fluorescent Color Code

et al. 2018

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This study convincingly demonstrates a unique example of the self-assembly of a naphthalene diimide (NDI)-appended peptide into a fluorescent J-aggregate in aqueous media. Moreover, this aggregated species shows a remarkable yellow fluorescence in solid state, an unusual phenomenon for NDI-based compounds. The aggregated species has been characterized using transmission electron microscopy (TEM), Fourier-transform infrared spectroscopy, X-ray diffraction, time-correlated single proton counting (TCSPC), UV–vis, and photoluminescence studies. TEM images reveal cross-linked nanofibrillar morphology of this aggregated species in water (pH 7.4). TCSPC study clearly indicates that the aggregated species in water has a higher average lifetime compared to that of the non-aggregated species. Interestingly, this NDI-based peptide shows H + ion concentration-dependent change in the emission property in water. The fluorescence output is erased completely in the presence of an alkali, and it reappears in the presence of an acid, indicating its erasing and rewritable property. This indicates its probable use in authentication tools for security purposes as a rewritable fluorescence color code. This NDI-appended peptide-based molecule can be used for encryption of information due to erasing and rewritable property of the molecule in the aggregated state in aqueous medium.

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Section: Introductionmentioning

confidence: 99%

Luminescent Naphthalene Diimide-Based Peptide in Aqueous Medium and in Solid State: Rewritable Fluorescent Color Code

et al. 2018

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“…'Ionic self-assembly', described as the cooperative assembly of charged surfactants and oppositely charged building blocks, is a well-established method for the creation of functional materials. [48][49][50] Of particular interest is the cooperative electrostatic surfactant binding to oppositely charged polyelectrolytes. [51][52] N-acyl-amino acid chiral anionic surfactants (which feature a tetrahedral chiral carbon center at a position adjacent to the anionic carboxylate functional group, Fig.…”

Section: Introductionmentioning

confidence: 99%

Chiral Transmission to Cationic Polycobaltocenes over Multiple Length Scales Using Anionic Surfactants

Musgrave¹,

Choi²,

Harniman³

et al. 2018

J. Am. Chem. Soc.

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Chiral polymers are ubiquitous in nature, and the self-assembly of chiral materials is a field of widespread interest. In this paper, we describe the formation of chiral metallopolymers based on poly(cobaltoceniumethylene) ([PCE] ), which have been prepared through oxidation of poly(cobaltocenylethylene) (PCE) in the presence of enantiopure N-acyl-amino-acid-derived anionic surfactants, such as N-palmitoyl-l-alanine (C-l-Ala) and N-palmitoyl-d-alanine (C-d-Ala). It is postulated that the resulting metallopolymer complexes [PCE][C-l/d-Ala] contain close ionic contacts, and exhibit chirality through the axially chiral ethylenic CH-CH bridges, leading to interaction of the chromophoric [CoCp] units through chiral space. The steric influence of the long palmitoyl (C) surfactant tail is key for the transmission of chirality to the polymer, and results in a brushlike amphiphilic macromolecular structure that also affords solubility in polar organic solvents (e.g., EtOH, THF). Upon dialysis of these solutions into water, the hydrophobic palmitoyl surfactant substituents aggregate and the complex assembles into superhelical ribbons with identifiable "handedness", indicating the transmission of chirality from the molecular surfactant to the micrometer length scale, via the macromolecular complex.

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“…The chirality of the designed PPA is investigated by circular dichroism (CD) spectroscopy which exhibits signals in CD spectra (Figure a) and a strong bisignate Cotton effect ,. PPA shows positive maximum at 541, 371 nm and negative maximum at 462 nm.…”

Section: Resultsmentioning

confidence: 99%

Optoelectronic Properties of Supramolecular Aggregates of Phenylalanine Conjugated Perylene Bisimide

2018

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Perylene derivatives exhibit good optoelectronic properties and in order to augment it, the self‐assembly of phenyl alanine conjugated with perylene bisimide (PBI) would be a good motif because of excellent self‐organizing power of both the components. So we have synthesized N, N’‐di((S)‐1‐carboxylphenylalanine)‐3,4:9,10‐ perylenetetracarboxyl bisimide (PPA) and have studied its self‐organization in different organic solvents. Microscopic images reveal the formation of vesicles cast from chloroform. There is a gradual change in color from green to yellow to orange to red under UV light with increasing PPA concentration. The emission maximum for the lowest energy peak gradually increases with increase in PPA concentration and the emission intensity shows a maximum at a 4–8 mM concentration due to variation of self‐aggregation nature. Fluorescence of PPA in other solvents also varies in a similar fashion indicating dynamic nature of the self‐assembly with concentration. The current voltage (I−V) property of the dried ensemble from chloroform exhibit negative differential resistance with rectification property indicating co‐existence of holes and electrons. On application of electric field the holes and electrons of the system become recombined generating luminescence, which peak position and intensity vary with increasing applied voltage.

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Chiral Perylene Materials by Ionic Self-Assembly

Cited by 23 publications

References 61 publications

Luminescent Naphthalene Diimide-Based Peptide in Aqueous Medium and in Solid State: Rewritable Fluorescent Color Code

Luminescent Naphthalene Diimide-Based Peptide in Aqueous Medium and in Solid State: Rewritable Fluorescent Color Code

Chiral Transmission to Cationic Polycobaltocenes over Multiple Length Scales Using Anionic Surfactants

Optoelectronic Properties of Supramolecular Aggregates of Phenylalanine Conjugated Perylene Bisimide

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