Browse
Submit Data
Databases
API
Help

Dataset Information

46 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Self-sorted Oligophenylvinylene and Perylene Bisimide Hydrogels.

ABSTRACT: We describe two component hydrogels with networks composed of self-sorted fibres. The component gelators are based on 1,4-distyrylbenzene (OPV3) and perylene bisimide (PBI) units. Self-sorted gels can be formed by a slow decrease in pH, which leads to sequential assembly. We demonstrate self-sorting by NMR, rheology and small angle X-ray scattering (SAXS). Photoconductive xerogels can be prepared by drying these gels. The wavelength response of the xerogel is different to that of the PBI alone.

SUBMITTER: Castilla AM

PROVIDER: S-EPMC5566499 | biostudies-literature | 2017 Aug

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Self-sorted Oligophenylvinylene and Perylene Bisimide Hydrogels.

Castilla Ana M AM Draper Emily R ER Nolan Michael C MC Brasnett Christopher C Seddon Annela A Mears Laura L E LLE Cowieson Nathan N Adams Dave J DJ

Scientific reports 20170821 1

We describe two component hydrogels with networks composed of self-sorted fibres. The component gelators are based on 1,4-distyrylbenzene (OPV3) and perylene bisimide (PBI) units. Self-sorted gels can be formed by a slow decrease in pH, which leads to sequential assembly. We demonstrate self-sorting by NMR, rheology and small angle X-ray scattering (SAXS). Photoconductive xerogels can be prepared by drying these gels. The wavelength response of the xerogel is different to that of the PBI alone. ...[more]

PMID: 28827598

Similar Datasets

Mechanoresponsive Self-Assembled Perylene Bisimide Films.

Project description:In this work, self-assembled amino-acid appended perylene bisimides (PBIs) have been studied that when processed into thin films change their resistivity in response to being bent. The PBIs assemble into structures in water and form thin films upon drying. These normally delicate thin films can be tolerant to bending, depending on the aggregates they form. Furthermore, the films then reversibly change their resistivity in response to this mechanical stimulus. This change is proportional to the degree of bending of the film giving them the potential to be used quantitatively to measure mechanical movement, such as in wearable devices.

| S-EPMC7522684 | biostudies-literature

Perylene bisimide hydrogels and lyotropic liquid crystals with temperature-responsive color change.

Project description:The self-assembly of perylene bisimide (PBI) dyes bearing oligo ethylene glycol (OEG) units in water affords responsive functional nanostructures characterized by their lower critical solution temperature (LCST). Tuning of the LCST is realized by a supramolecular approach that relies on two structurally closely related PBI-OEG molecules. The two PBIs socially co-assemble in water and the resulting nanostructures exhibit a single LCST in between the transition temperatures of the aggregates formed by single components. This permits to precisely tune the transition from a hydrogel to a lyotropic liquid crystal state at temperatures between 26 and 51 °C by adjusting the molar fraction of the two PBIs. Owing to concomitant changes in PBI-PBI interactions this phase transition affords a pronounced color change with "fluorescence-on" response that can be utilized as a smart temperature sensory system.

| S-EPMC5356028 | biostudies-literature

Organic Acid Regulated Self-Assembly and Photophysical Properties of Perylene Bisimide Derivatives.

Project description:In this work, perylene bisimide derivatives (PBI-1 and PBI-2) with tertiary amine groups were designed and synthesized. To control the final morphologies and properties of their aggregates, seven kinds of organic acids were used to alter the self-assembly environment. The influence of organic acids on the morphology of the aggregates was investigated. Photophysical properties of the aggregates were markedly affected by the kind and concentration of the organic acid. The thermal and gas sensitivities of the PBI-1 aggregates were studied with the use of UV-visible spectroscopy and digital imaging. The shift of the UV-visible spectra varied with time, temperature, acid type and acid concentration. Furthermore, PBI-1 aggregates showed a red-to-blue color change after addition of seven organic acids, whereas the color of the PBI-2 aggregates remained red. These changes of morphologies, photophysical properties and their thermal and gas sensitivities make these aggregates potentially useful in the fields of optoelectronics or sensors.

| S-EPMC7178315 | biostudies-literature

Synthesis and Photocontrolled Supramolecular Self-Assembly of Azobenzene-Functionalized Perylene Bisimide Derivatives.

Project description:Azobenzene (Azo) units were successfully introduced into perylene bisimide (PBI) structures in order to realize the photocontrolling of the morphology of the supramolecular assembly of PBI by a photoisomerization process. A total of three Azo-functionalized perylene bisimide derivatives (PBI1, PBI2, and PBI3) with different alkyl chain lengths were designed and synthesized by imidization of 3,4,9,10-perylene tetracarboxylic dianhydride with the corresponding amines. The structures of these compounds were characterized by proton nuclear magnetic resonance (1H NMR) and matrix-assisted laser desorption ionization time-of-flight mass spectrometry (MALDI-TOF-MS). The photoisomerization behaviors of Azo units in PBIs were investigated using ultraviolet-visible (UV-VIS) absorption spectroscopy, which were obviously effected by solvents and the alkyl chain length. Furthermore, the photoisomerization of Azo units has the obviously regulatory effect on the morphology of supramolecular assembly of PBIs, especially for the medium-length alkyl chain-linked Azo-functionalized PBI derivative (PBI2). This research realized the photocontrolling of the morphology of the supramolecular assembly of PBI derivatives by photoisomerization of Azo units.

| S-EPMC6681406 | biostudies-literature

Self-Sorting Supramolecular Polymerization: Helical and Lamellar Aggregates of Tetra-Bay-Acyloxy Perylene Bisimide.

Project description:A new perylene bisimide (PBI), with a fluorescence quantum yield up to unity, self-assembles into two polymorphic supramolecular polymers. This PBI bears four solubilizing acyloxy substituents at the bay positions and is unsubstituted at the imide position, thereby allowing hydrogen-bond-directed self-assembly in nonpolar solvents. The formation of the polymorphs is controlled by the cooling rate of hot monomer solutions. They show distinctive absorption profiles and morphologies and can be isolated in different polymorphic liquid-crystalline states. The interchromophoric arrangement causing the spectral features was elucidated, revealing the formation of columnar and lamellar phases, which are formed by either homo- or heterochiral self-assembly, respectively, of the atropoenantiomeric PBIs. Kinetic studies reveal a narcissistic self-sorting process upon fast cooling, and that the transformation into the heterochiral (racemic) sheetlike self-assemblies proceeds by dissociation via the monomeric state.

| S-EPMC7540443 | biostudies-literature

Tandem reactions in self-sorted catalytic molecular hydrogels.

Project description:By equipping mutually incompatible carboxylic acid and proline catalytic groups with different self-assembling motives we have achieved self-sorting of the resulting catalytic gelators, namely SucVal8 and ProValDoc, into different supramolecular fibers, thus preventing the acidic and basic catalytic groups from interfering with each other. The resulting spatial separation of the incompatible catalytic functions is found to be essential to achieve one-pot deacetalization-aldol tandem reactions with up to 85% efficiency and 90% enantioselectivity. On the contrary, when SucVal8 was co-assembled with a structurally similar catalytically active hydrogelator (ProVal8), self-sorting was precluded and no tandem catalysis was observed.

| S-EPMC6021788 | biostudies-other

Hydrogen-bonded perylene bisimide J-aggregate aqua material.

Project description:A new twelvefold methoxy-triethyleneglycol-jacketed tetraphenoxy-perylene bisimide (MEG-PBI) amphiphile was synthesized that self-assembles into two types of supramolecular aggregates in water: red-coloured aggregates of low order and with weak exciton coupling among the PBIs and blue-coloured strongly coupled J-aggregates consisting of a highly ordered hydrogen-bonded triple helix of PBIs. At room temperature this PBI is miscible with water at any proportions which enables the development of robust dye aggregates in solution, in hydrogel states and in lyotropic liquid crystalline states. In the presence of 60-95 wt% water, self-standing coloured hydrogels exhibit colour changes from red to blue accompanied by a fluorescence light-up in the far-red region upon heating in the range of 30-50 °C. This phenomenon is triggered by an entropically driven temperature-induced hydrogen-bond-directed slipped stacking arrangement of the MEG-PBI chromophores within structurally well-defined J-aggregates. This versatile aqua material is the first example of a stable PBI J-aggregate in water. We anticipate that this study will open a new avenue for the development of biocompatible functional materials based on self-assembled dyes and inspire the construction of other hydrogen-bonded supramolecular materials in the highly competitive solvent water.

| S-EPMC6124903 | biostudies-other

Globular Aggregates Stemming from the Self-Assembly of an Amphiphilic N-Annulated Perylene Bisimide in Aqueous Media.

Project description:Herein, we describe the synthesis of highly emissive amphiphilic N-annulated PBI 1 decorated with oligo ethylene glycol (OEG) side chains. These polar side chains allow the straightforward solubility of 1 in solvents of different polarity such as water, iPrOH, dioxane, or chloroform. Compound 1 self-assembles in aqueous media by π-stacking of the aromatic units and van der Waals interactions, favored by the hydrophobic effect. The hypo- and hypsochromic effect observed in the UV-Vis spectra of 1 in water in comparison to chloroform is diagnostic of H-type aggregation. Solvent denaturation experiments allow deriving the free Gibbs energy for the self-assembly process in aqueous media and the factor m that is indicative of the influence exerted by a good solvent in the stability of the final aggregates. The ability of compound 1 to self-assemble in water yields globular aggregates that have been visualized by TEM imaging.

| S-EPMC8228590 | biostudies-literature

Green Perylene Bisimide Dyes: Synthesis, Photophysical and Electrochemical Properties.

Project description:Three asymmetric amino-substituted perylene bisimide dyes with different n-alkyl chain lengths (n = 6, 12, or 18), 1-(N,N-dialkylamino)perylene bisimides (1a-1c), were synthesized under mild condition in high yields and were characterized by ¹H NMR, ¹³C NMR (nuclear magnetic resonance), HRMS (High Resolution Mass Spectrometer), UV-Vis and fluorescence spectra, as well as cyclic voltammetry (CV). These molecules show intense green color in both solution and solid state and are highly soluble in dichloromethane and even in nonpolar solvents, such as hexane. The shapes of the absorption spectra of 1a-1c in solid state and in solution were found to be virtually the same, indicating that the long alkyl chains could efficiently prevent aggregation. They exhibit a unique charge transfer emission in the near-infrared region, of which the peak wavelengths show strong solvatochromism. The dipole moments of the compounds have been estimated using the Lippert-Mataga equation, and upon excitation, they show larger dipole moment changes than that of 1-aminoperylene bisimide (2). Furthermore, all of the compounds exhibit two quasi-reversible one-electron oxidations and two quasi-reversible one-electron reductions in dichloromethane at modest potentials. Complementary density functional theory (DFT) calculations performed on these dyes are reported in order to rationalize their molecular structures and electronic properties.

| S-EPMC5456190 | biostudies-other

New fluorescent perylene bisimide indicators--a platform for broadband pH optodes.

Project description:Asymmetric perylene bisimide (PBI) dyes are prepared and are shown to be suitable for the preparation of fluorescence chemosensors for pH. They carry one amino-functional substituent which introduces pH sensitivity via photoinduced electron transfer (PET) while the other one increases solubility. The luminescence quantum yields for the new indicators exceed 75% in the protonated form. The new indicators are non-covalently entrapped in polyurethane hydrogel D4 and poly(hydroxyalkylmethacrylates). Several PET functions including aliphatic and aromatic amino groups were successfully used to tune the dynamic range of the sensor. Because of their virtually identical spectral properties, various PBIs with selected PET functions can easily be integrated into a single sensor with enlarged dynamic range (over 4 pH units). PBIs with two different substitution patterns in the bay position are investigated and possess variable spectral properties. Compared with their tetrachloro analogues, tetra-tert-butyl-substituted PBIs yield more long-wave excitable sensors which feature excellent photostability. Cross-sensitivity to ionic strength was found to be negligible. The practical applicability of the sensors may be compromised by the long response times (especially in case of tetra-tert-butyl-substituted PBIs).

| S-EPMC3100492 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data