Browse
Submit Data
Databases
API
Help

Dataset Information

11 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Synthesis and Thermal, Photophysical, Electrochemical Properties of 3,3-di[3-Arylcarbazol-9-ylmethyl]oxetane Derivatives.

ABSTRACT: Novel oxetane-functionalized derivatives were synthesized to find the impact of carbazole substituents, such as 1-naphtyl, 9-ethylcarbazole and 4-(diphenylamino)phenyl, on their thermal, photophysical and electrochemical properties. Additionally, to obtain the optimized ground-state geometry and distribution of the frontier molecular orbital energy levels, density functional theory (DFT) calculations were used. Thermal investigations showed that the obtained compounds are highly thermally stable up to 360 °C, as molecular glasses with glass transition temperatures in the range of 142-165 °C. UV-Vis and photoluminescence studies were performed in solvents of differing in polarity, in the solid state as a thin film on glass substrate, and in powders, and were supported by DFT calculations. They emitted radiation both in solution and in film with photoluminescence quantum yield from 4% to 87%. Cyclic voltammetry measurements revealed that the materials undergo an oxidation process. Next, the synthesized molecules were tested as hole transporting materials (HTM) in perovskite solar cells with the structure FTO/b-TiO₂/m-TiO₂/perovskite/HTM/Au, and photovoltaic parameters were compared with the reference device without the oxetane derivatives.

SUBMITTER: Korzec M

PROVIDER: S-EPMC8509391 | biostudies-literature |

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

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

α- and β-Substituted Metal-Free Phthalocyanines: Synthesis, Photophysical and Electrochemical Properties.

Project description:Two novel phthalonitrile derivatives, bearing two hexyloxy groups and a benzodioxin (or a naphthodioxin) annulated ring, along with their corresponding metal-free phthalocyanines (H2Pc) were prepared. FT-IR, mass, electronic absorption, 1H NMR, and 13C NMR spectroscopy were employed for the characterization of all compounds. The effect of hexadeca substituents on the photophysical properties of metal-free Pcs was investigated. Photophysical properties of H2Pc were studied in tetrahydrofuran (THF). Fluorescent quantum yields of phthalocyanines (Pcs) were calculated and compared with the unsubstituted phthalocyanine. 1,4-Benzoquinone effectively quenched the fluorescence of these compounds in THF. Cyclic and square wave voltammetry methods were applied to metal-free phthalocyanines and Pc-centered oxidation and reduction processes were obtained.

| S-EPMC7024180 | biostudies-literature

Highly Emissive 9-Borafluorene Derivatives: Synthesis, Photophysical Properties and Device Fabrication.

Project description:A series of 9-borafluorene derivatives, functionalised with electron-donating groups, have been prepared. Some of these 9-borafluorene compounds exhibit strong yellowish emission in solution and in the solid state with relatively high quantum yields (up to 73.6 % for FMesB-Cz as a neat film). The results suggest that the highly twisted donor groups suppress charge transfer, but the intrinsic photophysical properties of the 9-borafluorene systems remain. The new compounds showed enhanced stability towards the atmosphere, and exhibited excellent thermal stability, revealing their potential for application in materials science. Organic light-emitting diode (OLED) devices were fabricated with two of the highly emissive compounds, and they exhibited strong yellow-greenish electroluminescence, with a maximum luminance intensity of >22 000 cd m-2 . These are the first two examples of 9-borafluorene derivatives being used as light-emitting materials in OLED devices, and they have enabled us to achieve a balance between maintaining their intrinsic properties while improving their stability.

| S-EPMC8048904 | biostudies-literature

Synthesis and photophysical properties of novel benzophospholo[3,2-b]indole derivatives.

Project description:The parent benzophospholo[3,2-b]indole was prepared by the reaction of dichlorophenylphosphine with a dilithium intermediate, which was prepared in two steps from 2-ethynyl-N,N-dimethylaniline. Using the obtained benzophosphole-fused indole as a common starting material, simple modifications were carried out at the phosphorus center of the phosphole, synthesizing various functionalized analogs. The X-ray structure analysis of trivalent phosphole and phosphine oxide showed that the fused tetracyclic moieties are planar. The benzophosphole-fused indoles, such as phosphine oxide, phospholium salt, and borane complex, exhibited strong photoluminescence in dichloromethane (Φ = 67-75%).

| S-EPMC5687007 | biostudies-literature

Highly Luminescent 4H-1,2,4-Triazole Derivatives: Synthesis, Molecular Structure and Photophysical Properties.

Project description:An alternative approach to the Suzuki cross-coupling reaction is used to synthesize a series of new luminophores based on 4-alkyl-4H-1,2,4-triazole cores conjugated via 1,4-phenylene linker to fused-bicyclic and tricyclic aromatic, or heteroaromatic arrangements. The described methodology allows one to conduct the coupling reaction with the use of commercially available boronic acids in the presence of conventional solvents or ionic liquids and produced excellent yields. It was found that the use of ultrasounds or microwaves significantly accelerates the reaction. The obtained compounds exhibited high luminescent properties and a large quantum yield of emitted photons. The X-ray molecular structures of three highly conjugated 4H-1,2,4-triazole representatives are also presented.

| S-EPMC7764194 | biostudies-literature

Synthesis and Photophysical Properties of Fluorescent 6-Aryl-D-π-A Coumarin Derivatives.

Project description:A series of 6-aryl coumarin dyes were synthesized in satisfactory yields by Pd-catalyzed Suzuki cross-coupling reactions with a panel of boronic acids and coumarin bromides. Photophysical studies highlighted a large Stoke shift and interesting fluorescence quantum yield for these compounds. Optical properties were also investigated with the aid of quantum chemical calculations. The treatment of selected coumarin dyes with increasing amounts of trifluoroacetic acid showed that their fluorescence can be strongly influenced by pH (fluorescence quenching at high acid concentrations), while the addition of Fe3+ and Al3+ metal ions allowed to highlight dichotomous behavior with the corresponding reduction in fluorescence with the increase of [Fe3+] or [Al3+]. Finally, biological assays and fluorescence microscopy imaging investigations indicated that these compounds can be used as potential biomarkers in living and fixed cells.

| S-EPMC8675031 | biostudies-literature

Poly[(arylene ethynylene)-<i>alt</i>-(arylene vinylene)]s Based on Anthanthrone and Its Derivatives: Synthesis and Photophysical, Electrochemical, Electroluminescent, and Photovoltaic Properties.

Project description:Anthanthrone and its derivatives are large polycyclic aromatic compounds (PACs) that pose a number of challenges for incorporation into the structure of soluble conjugated polymers. For the first time, this group of PACs was employed as the building blocks for the synthesis of copolymers (P1-P5) based on poly[(arylene ethynylene)-alt-(arylene vinylene)]s backbone (-Ph-C≡C-Anth-C≡C-Ph-CH=CH-Ph-CH=CH-) n . During the synthesis of P1-P5, different alkyloxy side chains were incorporated in order to tune the properties of the polymers. Of the copolymer series only P1 (containing anthanthrone and branched 2-ethylhexyloxy side chains on phenylenes), P2 and P3 (for which the anthanthrones containing carbonyl groups were converted to anthanthrene containing alkyloxy substituents) were soluble. The photophysical, electrochemical, electroluminescent and photovoltaic properties of P1-P3 are reported, compared and discussed with respect to the effects of side chains.

| S-EPMC5688416 | biostudies-literature

Synthesis of 3,3'-di-O-methyl ardimerin and exploration of its DNA binding properties.

Project description:The 3,3'-di-O-methyl derivative (15) of the bis-C-aryl glycoside natural product ardimerin (1) has been synthesized in 11 steps from 2,3,4,6-tetrabenzylglucose (2) and 1,2,3-trimethoxybenzene (3). Key steps in the synthesis involve a Lewis acid mediated Friedel-Crafts type glycosylation and a Yamaguchi lactonization under Yonemitsu conditions. 3,3'-Di-O-methyl ardimerin aggregates in aqueous solutions at concentrations greater than 1 μM, and both UV and fluorescence binding studies indicate that 15 has a low affinity for duplex DNA.

| S-EPMC4067242 | biostudies-literature

Facile Synthesis and Evaluation of Electron Transport and Photophysical Properties of Photoluminescent PDI Derivatives.

Project description:Perylenediimides (PDIs) have emerged as potential materials for optoelectronic applications. In the current work, four PDI derivatives, substituted at imide nitrogen with 2,6-diisopropyl phenyl, 2-nitrophenyl, diphenylmethylene, and pentafluorophenyl groups, have been synthesized from perylene 3,4,9,10-tetracarboxylic dianhydride using a facile imidization synthesis process. PDI derivatives have been spectroscopically characterized for their structure and optical properties. Temperature-variable absorption and emission spectroscopy study confirmed the H-aggregation property. H-aggregation along with strong emission suggests the slipped π-π stacking of PDI molecules. Electrochemical analysis was performed for their redox behavior and calculation of lowest unoccupied molecular orbital and highest occupied molecular orbital energy levels. Scanning electron microscopy showed the formation of ordered structures. The PDI derivatives showed excellent electron conductivity without doping and 5-10× higher electron mobility than that of state-of-the-art fullerene acceptor phenyl-C61-butyric acid methyl ester (PC61BM). Finally, the charge generation and charge transfer phenomenon was studied by transient absorption spectroscopy (TAS). TAS showed ultrafast charge transfer from the poly(3-hexyl)thiophene (P3HT) donor polymer to PDI and formation of long-lived charge-separated states similar to fullerene derivative PC61BM/P3HT blends. Such PDI derivatives with excellent solubility and photophysical and electronic properties are potential n-type materials to be used in organic electronic devices.

| S-EPMC6881832 | biostudies-literature

Synthesis, Photophysical and Electronic Properties of New Red-to-NIR Emitting Donor-Acceptor Pyrene Derivatives.

Project description:We synthesized new pyrene derivatives with strong bis(para-methoxyphenyl)amine donors at the 2,7-positions and n-azaacene acceptors at the K-region of pyrene. The compounds possess a strong intramolecular charge transfer, leading to unusual properties such as emission in the red to NIR region (700?nm), which has not been reported before for monomeric pyrenes. Detailed photophysical studies reveal very long intrinsic lifetimes of >100?ns for the new compounds, which is typical for 2,7-substituted pyrenes but not for K-region substituted pyrenes. The incorporation of strong donors and acceptors leads to very low reduction and oxidation potentials, and spectroelectrochemical studies show that the compounds are on the borderline between localized Robin-Day class-II and delocalized Robin-Day class-III species.

| S-EPMC6973242 | 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