Browse
Submit Data
Databases
API
Help

Dataset Information

15 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Drastic Improvement of Air Stability in an n-Type Doped Naphthalene-Diimide Polymer by Thionation.

ABSTRACT: Organic thermoelectrics are attractive for the fabrication of flexible and cost-effective thermoelectric generators (TEGs) for waste heat recovery, in particular by exploiting large-area printing of polymer conductors. Efficient TEGs require both p- and n-type conductors: so far, the air instability of polymer n-type conductors, which typically lose orders of magnitude in electrical conductivity (σ) even for short exposure time to air, has impeded processing under ambient conditions. Here we tackle this problem in a relevant class of electron transporting, naphthalene-diimide copolymers, by substituting the imide oxygen with sulfur. n-type doping of the thionated copolymer gives rise to a higher σ with respect to the non-thionated one, and most importantly, owing to a reduced energy level of the lowest-unoccupied molecular orbital, σ is substantially stable over 16 h of air exposure. This result highlights the effectiveness of chemical tuning to improve air stability of n-type solution-processable polymer conductors and shows a path toward ambient large-area manufacturing of efficient polymer TEGs.

SUBMITTER: Nava D

PROVIDER: S-EPMC6166998 | biostudies-literature |

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

Novel Polyelectrolytes Based on Naphthalene Diimide with Different Counteranions for Cathode Interlayers in Polymer Solar Cells.

Project description:We synthesized novel polyelectrolytes based on naphthalene diimide with quaternary amine featuring hydroxyl groups at the side chain, along with different counteranions (PF-NDIN-Br-OH and PF-NDIN-I-OH) for polymer solar cell (PSC) application as the interlayer. The polyelectrolytes establish a beneficial interface dipole through the ionic moieties and synergistic effects arising from the hydroxyl groups located at the side chain. Incorporating polyelectrolytes as the cathode interlayer resulted in an enhancement of the power conversion efficiency (PCE). The PCE of the device with PF-NDIN-Br-OH increased from 8.96% to 9.51% compared to the ZnO-only device. The best PCE was obtained with the device based on PF-NDIN-I-OH, up to 9.59% resulting from the Jsc enhancement. This outcome implies a correlation between the performance of the device and the synergistic effects observed in polyelectrolytes containing hydroxyl groups in the side chain, along with larger anions when employed in PSCs.

| S-EPMC10779300 | biostudies-literature

Photogenerated charge transfer in Dion-Jacobson type layered perovskite based on naphthalene diimide.

Project description:Incorporating organic semiconducting spacer cations into layered lead halide perovskite structures provides a powerful approach to mitigate the typical strong dielectric and quantum confinement effects by inducing charge-transfer between the organic and inorganic layers. Herein we report the synthesis and characterization of thin films of novel DJ-phase organic-inorganic layered perovskite semiconductors using a naphthalene diimide (NDI) based divalent spacer cation, which is shown to accept photogenerated electrons from the inorganic layer. With alkyl chain lengths of 6 carbons, an NDI-based thin film exhibited electron mobility (based on space charge-limited current for quasi-layered 〈n〉 = 5 material) was found to be as high as 0.03 cm2 V-1 s-1 with no observable trap-filling region suggesting trap passivation by the NDI spacer cation.

| S-EPMC10246667 | biostudies-literature

Electron-to Hole Transport Change Induced by Solvent Vapor Annealing of Naphthalene Diimide Doped with Poly(3-Hexylthiophene).

Project description:Herein we report on fabrication and properties of organic field-effect transistors (OFETs) based on the spray-coated films of N,N'-dioctyl naphthalene diimide (NDIC8) doped with 2.4 wt% of poly (3-hexylthiophene) (P3HT). OFETs with the untreated NDIC8:P3HT films revealed electron conductivity [μe* = 5 × 10-4 cm2×(Vs)-1]. After the annealing in chloroform vapor the NDIC8:P3HT films revealed the hole transport only [μh* = 0.9 × 10-4 cm2×(Vs)-1]. Due to the chemical nature and energy levels, the hole transport was not expected for NDIC8-based system. Polarized optical- and scanning electron microscopies indicated that the solvent vapor annealing of the NDIC8:P3HT films caused a transition of their fine-grained morphology to the network of branched, dendritic crystallites. Grazing incidence wide-angle X-ray scattering studies indicated that the above transition was accompanied by a change in the crystal structure of NDIC8. The isotropic crystal structure of NDIC8 in the untreated film was identical to the known crystal structure of the bulk NDIC8. After the solvent annealing the crystal structure of NDIC8 changed to a not-yet-reported polymorph, that, unlike in the untreated film, was partially oriented with respect to the OFET substrate.

| S-EPMC8375403 | biostudies-literature

Redox-sensitive reversible self-assembly of amino acid-naphthalene diimide conjugates.

Project description:Peptide and low molecular weight amino acid-based materials that self-assemble in response to environmental triggers are highly desirable candidates in forming functional materials with tunable biophysical properties. In this paper, we explore redox-sensitive self-assembly of cationic phenylalanine derivatives conjugated to naphthalene diimide (NDI). Self-assembly of the cationic Phe-NDI conjugates into nanofibrils was induced in aqueous solvent at high ionic strength. Under reducing conditions, these self-assembled Phe-NDI conjugate fibrils underwent a morphological change to non-fibril aggregates. Upon reoxidation, the initially observed fibrils were reformed. The study herein provides an interesting strategy to effect reversible switching of the structure of supramolecular materials that can be applied to the development of sophisticated stimulus-responsive materials.

| S-EPMC5665789 | biostudies-literature

Anion-Controlled Architecture and Photochromism of Naphthalene Diimide-Based Coordination Polymers.

Project description:Three new cadmium coordination polymers, namely [Cd(NO₃)₂(DPNDI)(CH₃OH)]·CH₃OH (1), [Cd(SCN)₂(DPNDI)] (2), and [Cd(DPNDI)₂(DMF)₂]·2ClO₄ (3) (DPNDI = N,N-di(4-pyridyl)-1,4,5,8-naphthalene diimide, DMF = N,N-dimethylformamide) have been synthesized by reactions of DPNDI with Cd(NO₃)₂, Cd(SCN)₂, and Cd(ClO₄)₂, respectively. Compound 1 is a one-dimensional coordination polymer with strong lone pair-π interactions between the coordinated NO₃- anions and the imide ring of DPNDI; while 2 is a two-dimensional network with a (4, 4) net topology. In the case of 3, due to the presence of uncoordinated perchlorate counter ions, it exhibits a non-interpenetrated square-grid coordination polymer containing one-dimensional rhomboid channels. The structural diversity in these compounds is attributed to different coordination abilities and geometries of counter anions. Due to the presence of electron-deficient NDI moiety, the photochromic behavior of these compounds was studied. Interestingly, only compounds 1 and 3 exhibit color changes under light irradiation. The influence of the anions on the photochromism process of the NDI-based materials has been discussed.

| S-EPMC6415121 | biostudies-literature

Highly Planarized Naphthalene Diimide-Bifuran Copolymers with Unexpected Charge Transport Performance.

Project description:The synthesis, characterization, and charge transport performance of novel copolymers PNDIFu2 made from alternating naphthalene diimide (NDI) and bifuran (Fu2) units are reported. Usage of potentially biomass-derived Fu2 as alternating repeat unit enables flattened polymer backbones due to reduced steric interactions between the imide oxygens and Fu2 units, as seen by density functional theory (DFT) calculations and UV-vis spectroscopy. Aggregation of PNDIFu2 in solution is enhanced if compared to the analogous NDI-bithiophene (T2) copolymers PNDIT2, occurring in all solvents and temperatures probed. PNDIFu2 features a smaller π-π stacking distance of 0.35 nm compared to 0.39 nm seen for PNDIT2. Alignment of aggregates in films is achieved by using off-center spin coating, whereby PNDIFu2 exhibits a stronger dichroic ratio and transport anisotropy in field-effect transistors (FET) compared to PNDIT2, with an overall good electron mobility of 0.21 cm2/(V s). Despite an enhanced backbone planarity, the smaller π-π stacking and the enhanced charge transport anisotropy, the electron mobility of PNDIFu2 is about three times lower compared to PNDIT2. Density functional theory calculations suggest that charge transport in PNDIFu2 is limited by enhanced polaron localization compared to PNDIT2.

| S-EPMC5584907 | biostudies-literature

Conjoint use of Naphthalene Diimide and Fullerene Derivatives to Generate Organic Semiconductors for n-type Organic Thin Film Transistors.

Project description:In this paper, we described the design, synthesis, and characterization of two novel naphthalene diimide (NDI) core-based targets modified with terminal fullerene (C60 ) yield - so called S4 and S5, in which NDI bearing 1 and 2 molecules of C60 , respectively. The absorption, electrochemical and thin-film transistor characteristics of the newly developed targets were investigated in detail. Both S4 and S5 displayed broad absorption in the 450-500 nm region, owing to the effect of conjugation due to fullerene functionalities. The electrochemical measurement suggested that the HOMO and the LUMO energy levels can be altered with the number of C60 units. Both S4 and S5 were employed as organic semiconductor materials in n-channel transistors. The thin film transistor based on S4 exhibited superior electron mobility (μe) values ranging from 1.20×10-4 to 3.58×10-4 cm2 V-1 s-1 with a current on-off ratio varying from 102 to 103 in comparison with the performance of S5 based transistor, which exhibited μe ranging from 8.33×10-5 to 2.03×10-4 cm2 V-1 s-1 depending on channel lengths.

| S-EPMC8015730 | biostudies-literature

Mechanism of the antiproliferative activity of some naphthalene diimide G-quadruplex ligands.

Project description:G-quadruplexes are higher-order nucleic acid structures that can form in G-rich telomeres and promoter regions of oncogenes. Telomeric quadruplex stabilization by small molecules can lead to telomere uncapping, followed by DNA damage response and senescence, as well as chromosomal fusions leading to deregulation of mitosis, followed by apoptosis and downregulation of oncogene expression. We report here on investigations into the mechanism of action of tetra-substituted naphthalene diimide ligands on the basis of cell biologic data together with a National Cancer Institute COMPARE study. We conclude that four principal mechanisms of action are implicated for these compounds: 1) telomere uncapping with subsequent DNA damage response and senescence; 2) inhibition of transcription/translation of oncogenes; 3) genomic instability through telomeric DNA end fusions, resulting in mitotic catastrophe and apoptosis; and 4) induction of chromosomal instability by telomere aggregate formation.

| S-EPMC3558810 | biostudies-literature

Enhanced Li<sup>+</sup> charge storage in naphthalene diimide/vanadium pentoxide intercalates.

Project description:N,N'-Bis(4-aminophenyl)-1,4,5,8-naphthalene diimide (NDI-ph) was intercalated into lamellar vanadium pentoxide (V2O5) in different amounts to prepare hybrid intercalates. The presence of the imide supports the material's ability to form lithium salts with the structural stabilization of the oxide matrix. This effect is remarkable in charge/discharge cycles in terms of Li+ uptake and discharge by the lamellar intercalates, as we could double the ion uptake capacity (1.27 Li+ per V2O5 unit vs. 0.66 for pure V2O5), enhance the chemical reversibility and double the specific charge capacity (188 mA h g-1 vs. 98 mA h g-1 for pure V2O5) with very small amounts of this imide. This is the first paper dealing with naphthalene diimide intercalates in vanadium pentoxide xerogel for Li+ storage.

| S-EPMC9081847 | biostudies-literature

Naphthalene diimide bis-guanidinio-carbonyl-pyrrole as a pH-switchable threading DNA intercalator.

Project description:A novel naphthalene diimde analogue (NDI) equipped at the imide positions with two guanidinio-carbonyl-pyrrole (GCP) pendant arms interacted significantly stronger with ds-DNA at pH 5 than at pH 7, due to reversible protonation of the GCP arms. This was consequence of a pH-switchable threading intercalation into ds-DNAs only at pH 5, while at neutral conditions (pH 7) NDI-GCP2 switched to the DNA minor groove binding. Intriguingly, NDI-GCP2 was at both pH values studied bound to the ds-RNA major groove, still showing a higher affinity and thermal denaturation effect at pH 5 due to GCP protonation. At excess over the DNA/RNA conjugate NDI-GCP2 showed also aggregation along the ds-polynucleotide and AFM and DLS demonstrated that NDI-GCP2 has pronounced ds-DNA condensation ability.

| S-EPMC7492691 | 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