Browse
Submit Data
Databases
API
Help

Dataset Information

28 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Organogels Fabricated from Self-Assembled Nanotubes Containing Core Substituted Perylene Diimide Derivative.

ABSTRACT: Perylene-based organogels are well-known for their applications as sensors and optoelectronic materials. Among them, core-substituted perylene diimide-based organogels are rarely explored. Herein, the hierarchical self-assembly mechanism of a newly synthesized, amide-linked core-substituted perylene diimide derivative, which formed organogels in organic solvents like toluene and methyl cyclohexane (MCH), is discussed. These organogels are composed of one-dimensional molecular aggregates like nanofibers and nanotubes. Organogels composed of nanofibers are very frequent. On the contrary, for the first time, we have encountered a perylene diimide-based organogel consisting of self-assembled nanotubes. The molecular interactions, molecular packing, and rheological properties of this organogel are also discussed.

SUBMITTER: Moharana P

PROVIDER: S-EPMC9245106 | biostudies-literature |

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

Simple Perylene Diimide Cyclohexane Derivative With Combined CPL and TPA Properties.

Project description:In this work we describe the linear and non-linear (chiro)optical properties of an enantiopure bis-perylenediimide (PDI) cyclohexane derivative. This compound exhibits upconversion based on a two-photon absorption (TPA) process with a cross-section value of 70 GM together with emission of circularly polarized luminescence (CPL), showing a glum in the range of 10-3. This simple structure represents one of the scarce examples of purely organic compounds combining both TPA and CPL responses, together with large values of molar absorptivity and fluorescence quantum yield with emission in the 500-600 nm. Self-assembly induced by introduction of a poor solvent allows for a spectacular shift of the emission into the near-infrared (NIR, 650-750 nm) by formation of well-defined rotationally displaced dimers. Therefore, we are here presenting a versatile platform whose optical properties can be simply tuned by self-assembly or by functionalization of the electron-deficient aromatic core of PDIs.

| S-EPMC7186504 | biostudies-literature

Synthesis and Self-Assembly of Bay-Substituted Perylene Diimide Gemini-Type Surfactants as Off-On Fluorescent Probes for Lipid Bilayers.

Project description:Interest in bay-substituted perylene-3,4:9,10-tetracarboxylic diimides (PDIs) for solution-based applications is growing due to their improved solubility and altered optical and electronic properties compared to unsubstituted PDIs. Synthetic routes to 1,12-bay-substituted PDIs have been very demanding due to issues with steric hindrance and poor regioselectivity. Here we report a simple one-step regioselective and high yielding synthesis of a 1,12-dihydroxylated PDI derivative that can subsequently be alkylated in a straightforward fashion to produce nonplanar 1,12-dialkoxy PDIs. These PDIs show a large Stokes shift, which is specifically useful for bioimaging applications. A particular cationic PDI gemini-type surfactant has been developed that forms nonfluorescent self-assembled particles in water ("off state"), which exerts a high fluorescence upon incorporation into lipophilic bilayers ("on state"). Therefore, this probe is appealing as a highly sensitive fluorescent labelling marker with a low background signal for imaging artificial and cellular membranes.

| S-EPMC6001554 | biostudies-literature

Electron Acceptors With a Truxene Core and Perylene Diimide Branches for Organic Solar Cells: The Effect of Ring-Fusion.

Project description:In this work, a star-shaped planar acceptor named FTr-3PDI was synthesized via ring-fusion between truxene core and three bay-linked perylene diimide (PDI) branches. Compared to the unfused non-planar acceptor Tr-3PDI, FTr-3PDI exhibits better structural rigidity and planarity, as well as more effective conjugation between truxene core and PDI branches. As a result, FTr-3PDI shows up-shifted energy levels, enhanced light absorption coefficient, increased electron mobility, and more favorable phase separation morphology in bulk-heterojunction (BHJ) blend films as compared to Tr-3PDI. Consequently, FTr-3PDI afforded higher power conversion efficiency (PCE) in BHJ solar cells when blended with a polymer donor PTB7-Th. This work demonstrates that ring-fusion is a promising molecular design strategy to combine the merits of truxene and PDI for non-fullerene acceptors used in organic solar cells.

| S-EPMC6131300 | biostudies-literature

An ambient stable core-substituted perylene bisimide dianion: isolation and single crystal structure analysis.

Project description:Here we report the first example of an isolable, ambient stable perylene bisimide (PBI) dianion which was synthesized by catalytic reduction of a highly electron deficient PBI derivative. The remarkable stability of this unprecedented dianion in air for months facilitated its complete characterization by different methods, including single crystal X-ray analysis. Furthermore, solvent dependent cyclic and square wave voltammetry studies revealed that the formation of PBI dianions is preferred in more polar solvents, whereas the generation of PBI radical anions should be favoured in less polar solvents.

| S-EPMC5501005 | biostudies-literature

Perylene Diimide as a Precise Graphene-like Superoxide Dismutase Mimetic.

Project description:Here we show that the active portion of a graphitic nanoparticle can be mimicked by a perylene diimide (PDI) to explain the otherwise elusive biological and electrocatalytic activity of the nanoparticle construct. Development of molecular analogues that mimic the antioxidant properties of oxidized graphenes, in this case the poly(ethylene glycolated) hydrophilic carbon clusters (PEG-HCCs), will afford important insights into the highly efficient activity of PEG-HCCs and their graphitic analogues. PEGylated perylene diimides (PEGn-PDI) serve as well-defined molecular analogues of PEG-HCCs and oxidized graphenes in general, and their antioxidant and superoxide dismutase-like (SOD-like) properties were studied. PEGn-PDIs have two reversible reduction peaks, which are more positive than the oxidation peak of superoxide (O2•-). This is similar to the reduction peak of the HCCs. Thus, as with PEG-HCCs, PEGn-PDIs are also strong single-electron oxidants of O2•-. Furthermore, reduced PEGn-PDI, PEGn-PDI•-, in the presence of protons, was shown to reduce O2•- to H2O2 to complete the catalytic cycle in this SOD analogue. The kinetics of the conversion of O2•- to O2 and H2O2 by PEG8-PDI was measured using freeze-trap EPR experiments to provide a turnover number of 133 s-1; the similarity in kinetics further supports that PEG8-PDI is a true SOD mimetic. Finally, PDIs can be used as catalysts in the electrochemical oxygen reduction reaction in water, which proceeds by a two-electron process with the production of H2O2, mimicking graphene oxide nanoparticles that are otherwise difficult to study spectroscopically.

| S-EPMC5333640 | biostudies-literature

Thionated Perylene Diimide-Phenothiazine Dyad: Synthesis, Structure, and Electrochemical Studies.

Project description:Perylene diimides (PDIs) are promising candidates for n-type semiconductor materials and, thus, for use in organic electronics. Thionation of the imide moiety provides an efficient strategy to control the donor-acceptor gap of these types of compounds, although the degree and selectivity of thionation can be hard to achieve. Through the design of a sterically encumbered PDI-phenothiazine dyad, a previously unattained geminal thionation pattern has been realized, providing the first example of a perylene-monoimide-monothioimide. The electrochemical and solid-state structural properties of this uniquely thionated dyad are reported and compared to those of the nonthionated parent molecule. It is found that thionation enhances the electron affinity of the PDI core, affecting electrochemical and spectroelectochemcial behavior of the dyad without significantly affecting the solid-state packing of the molecules.

| S-EPMC6644668 | biostudies-literature

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

Synthesis and Optoelectronic Characterization of Perylene Diimide-Quinoline Based Small Molecules.

Project description:Perylene diimide (PDI) is one of the most studied functional dyes due to their structural versatility and fine tuning of the materials properties. Core substituted PDIs are prominent n-type semiconductor materials that could be used as non-fullerene acceptors in organic photovoltaics. Herein, we develop versatile organic building blocks based on PDI by decorating the PDI core with quinoline groups. Styryl and hydroxy phenyl mono and difunctionalized molecules were prepared using mono-nitro and dibromo bay substituted PDIs by Suzuki coupling with the respective boronic acid derivatives. A novel methodology using nitro-PDI under Suzuki coupling conditions as an electrophile partner was successfully tested. Furthermore, the PDI derivatives were used for the synthesis of soluble, electron accepting small molecules combining PDI with weak electron withdrawing quinoline derivatives. The new molecules presented wide absorbance in the visible spectrum from 450 to almost 700 nm while their LUMO levels and their energy levels are in the range of -3.8 to -4.2 eV.

| S-EPMC6930630 | biostudies-literature

Photophysics of Perylene Diimide Dianions and Their Application in Photoredox Catalysis.

Project description:The two-electron reduced forms of perylene diimides (PDIs) are luminescent closed-shell species whose photochemical properties seem underexplored. Our proof-of-concept study demonstrates that straightforward (single) excitation of PDI dianions with green photons provides an excited state that is similarly or more reducing than the much shorter-lived excited states of PDI radical monoanions, which are typically accessible after biphotonic excitation with blue photons. Thermodynamically demanding photocatalytic reductive dehalogenations and reductive C-O bond cleavage reactions of lignin model compounds have been performed using sodium dithionite acts as a reductant, either in aqueous solution or in biphasic water-acetonitrile mixtures in the presence of a phase transfer reagent. Our work illustrates the concept of multi-electron reduction of a photocatalyst by a sacrificial reagent prior to irradiation with low-energy photons as a means of generating very reactive excited states.

| S-EPMC9299816 | biostudies-literature

Crystallization Control of <i>N,N'</i>-Dioctyl Perylene Diimide by Amphiphilic Block Copolymers Containing poly(3-Hexylthiophene) and Polyethylene Glycol.

Project description:The preparation of micron- to nanometer-sized functional materials with well-defined shapes and packing is a key process to their applications. There are many ways to control the crystal growth of organic semiconductors. Adding polymer additives has been proven a robust strategy to optimize semiconductor crystal structure and the corresponding optoelectronic properties. We have found that poly(3-hexylthiophene) (P3HT) can effectively regulate the crystallization behavior of N,N'-dioctyl perylene diimide (C8PDI). In this study, we combined P3HT and polyethylene glycol (PEG) to amphiphilic block copolymers and studied the crystallization modification effect of these block copolymers. It is found that the crystallization modification effect of the block copolymers is retained and gradually enhanced with P3HT content. The length of C8PDI crystals were well controlled from 2 to 0.4 μm, and the width from 210 to 35 nm. On the other hand, due to the water solubility of PEG block, crystalline PEG-b-P3HT/C8PDI micelles in water were successfully prepared, and this water phase colloid could be stable for more than 2 weeks, which provides a new way to prepare pollution-free aqueous organic semiconductor inks for printing electronic devices.

| S-EPMC8222538 | 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