Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Monosulfonicpillar[5]arene: Synthesis, Characterization, and Complexation with Tetraphenylethene for Aggregation-Induced Emission.

ABSTRACT: A pillar[5]arene derivative with a hydrophilic sulfonic group, i.e., monosulfonicpillar[5]arene (MSP5), has been successfully synthesized for the first time, which exhibited strong binding affinity towards alcohol analogs. Significantly, fluorescent supramolecular ensemble was fabricated from the supramolecular complexation of MSP5 and a neutral guest with tetraphenylethene core. Enhanced fluorescent emission of this system can be detected both in dilute solution and the solid state, and its temperature and competitive guest multi-responsive properties suggest its promising application as a chemical sensor towards alcohol analogs, ethylenediamine, and temperature variations.

SUBMITTER: Jin XY

PROVIDER: S-EPMC5838235 | biostudies-other | 2018 Mar

REPOSITORIES: biostudies-other

ACCESS DATA

Json Xml

Publications

Monosulfonicpillar[5]arene: Synthesis, Characterization, and Complexation with Tetraphenylethene for Aggregation-Induced Emission.

Jin Xiao-Yu XY Song Nan N Wang Xu X Wang Chun-Yu CY Wang Yan Y Yang Ying-Wei YW

Scientific reports 20180305 1

A pillar[5]arene derivative with a hydrophilic sulfonic group, i.e., monosulfonicpillar[5]arene (MSP5), has been successfully synthesized for the first time, which exhibited strong binding affinity towards alcohol analogs. Significantly, fluorescent supramolecular ensemble was fabricated from the supramolecular complexation of MSP5 and a neutral guest with tetraphenylethene core. Enhanced fluorescent emission of this system can be detected both in dilute solution and the solid state, and its tem ...[more]

PMID: 29507324

Similar Datasets

Synthesis, characterization, aggregation-induced emission, solvatochromism and mechanochromism of fluorinated benzothiadiazole bonded to tetraphenylethenes.

Project description:Compounds consisting of unsubstituted, monofluoro and difluoro substituted benzothiadiazole bonded to two tetraphenylethenes were successfully prepared by palladium catalyzed Suzuki-Miyaura cross-coupling reaction of their corresponding co-monomers. All compounds exhibited aggregation-induced emission characteristics when the water fraction was higher than 60% in the THF/water mixtures. The emission maximum for the three compounds was blue-shifted when the water content reached 90% compared to that in THF solution. The intensity of emission maximum of difluorinated benzothiadiazole linked with two tetraphenylethenes was 2.5 times higher in 90% water compared to those in THF solution. Surprisingly, two liquid crystal phases with two distinct emission colors were observed only for the compound containing difluorinated benzothiadiazole bonded to two tetraphenylethene. All compounds showed remarkable solvatochromic properties in selected solvents with different polarities. The powder XRD results and mechanochromism of the compounds suggested that the solid state structures can change from one form to another by grinding, fuming or annealing processes.

| S-EPMC9079628 | biostudies-literature

Synthesis of Novel Biocompatible Thienopyrimidine Chromophores with Aggregation-Induced Emission Sensitive to Molecular Aggregation.

Project description:Biocompatible luminogens with aggregation-induced emission (AIE) have several applications in the biology field, such as in detecting biomacromolecules bioprobes and in bio-imaging. Due to their bioactivities and light-emitting properties, many heterocyclic compounds are good candidates for such applications. However, heterocyclic π-conjugated systems with AIE behavior remain rare as strong intermolecular π-π interactions usually quench their emission. In this work, new thienopyrimidine heterocyclic compounds were synthesized and their structures were verified by elemental analysis and Fourier transform infrared (FT-IR), 1H nuclear magnetic resonance (NMR), and 13C NMR spectra. The photophysical properties of some compounds were investigated in the solution and solid states. Density functional theory calculations were also performed to confirm the observed photophysical properties of the compounds. The studied dyes displayed AIE properties with spectral shapes related to the aggregate structure and a quantum yield up to 10.8%. The emission efficiency of the powder is attributed to the incorporation of multiply rotatable and twisted aryl groups to the fused heterocyclic moieties. The dyes also showed high thermal stability and potent antimicrobial activities against numerous bacterial and fungal strains. Additionally, the cytotoxicity of the new compounds was evaluated against the Caco-2 cell line, and molecular docking was used to investigate the binding conformation of the most effective compound with the MNK2 enzyme. Therefore, the presented structures may potentially be used for bioapplications.

| S-EPMC7689934 | biostudies-literature

Barbituric Acid Based Fluorogens: Synthesis, Aggregation-Induced Emission, and Protein Fibril Detection.

Project description:Fluorescent dyes, especially those emitting in the long wavelength region, are excellent candidates in the area of bioassay and bioimaging. In this work, we report a series of simple organic fluorescent dyes consisting of electron-donating aniline groups and electron-withdrawing barbituric acid groups. These dyes are very easy to construct while emitting strongly in the red region in their solid state. The photophysical properties of these dyes, such as solvatochromism and aggregation-induced emission, are systematically characterized. Afterward, the structure-property relationships of these barbituric acid based fluorogens are discussed. Finally, we demonstrate their potential applications for protein amyloid fibril detection.

| S-EPMC6982923 | biostudies-literature

Biological Synthesis and Process Monitoring of an Aggregation-Induced Emission Luminogen-Based Fluorescent Polymer.

Project description:As the most abundant and renewable biopolymer on earth, cellulose can be functionalized for various advanced applications by chemical modification. In addition, fluorescent polymers with aggregation-induced emission (AIE) are generally prepared using chemical approaches, and the biosynthesis of AIE-active polymers are rarely investigated. Herein, fluorescent cellulose was successfully synthesized by bacterial fermentation, where glucosamine-modified AIE luminogen was incorporated into cellulose to achieve AIE-active biopolymers. Excitingly, real-time visualization of the synthetic process was realized, which is crucial for investigating the process of bacterial fermentation. The biosynthesized cellulose exhibited better performance with uniform fluorescence distribution and high stability, compared with that prepared by physical absorption. Additionally, fluorescent mats were fabricated by electrospinning of AIE-active cellulose, demonstrating its great potential applications in flexible display and tissue engineering.

| S-EPMC9516714 | biostudies-literature

Aggregation-Induced Emission (AIE), Life and Health.

Project description:Light has profoundly impacted modern medicine and healthcare, with numerous luminescent agents and imaging techniques currently being used to assess health and treat diseases. As an emerging concept in luminescence, aggregation-induced emission (AIE) has shown great potential in biological applications due to its advantages in terms of brightness, biocompatibility, photostability, and positive correlation with concentration. This review provides a comprehensive summary of AIE luminogens applied in imaging of biological structure and dynamic physiological processes, disease diagnosis and treatment, and detection and monitoring of specific analytes, followed by representative works. Discussions on critical issues and perspectives on future directions are also included. This review aims to stimulate the interest of researchers from different fields, including chemistry, biology, materials science, medicine, etc., thus promoting the development of AIE in the fields of life and health.

| S-EPMC10416578 | biostudies-literature

Aggregation induced emission by pyridinium-pyridinium interactions.

Project description:Non-covalent intermolecular interactions between pyridinium subunits in a crystal-state are an efficient means to accomplish aggregation induced emission and avoid aggregation caused quenching.

| S-EPMC9059268 | biostudies-literature

Synthesis of new fluorescent molecules having an aggregation-induced emission property derived from 4-fluoroisoxazoles.

Project description:Fluorescent molecules based on a fluorinated isoxazole scaffold were synthesized and investigated for their photochemical properties. The introduction of a fluorine substituent into 3,5-diarylisoxazoles led to an increase of fluorescence intensity and exhibited a redshift in the emission intensity. ?-Fluorinated boron ketoiminates (F-BKIs) were also synthesized via a ring-opening reaction of 4-fluoroisoxazoles and exhibited highly fluorescent luminescence and aggregation-induced emission (AIE), showing promise as a new fluorophore.

| S-EPMC7323617 | biostudies-literature

Synthesis, aggregation induced emission and through space conjugation of triphenylvinylphenyl substituted [2.2]paracyclophane-1,9-diene.

Project description:4-Bromo substituted [2.2]paracyclophane-1,9-diene was synthesized from the corresponding dithia[3.3]paracyclophane in three steps through benzyne Steven rearrangement, oxidation, and a thermal elimination reaction. 4-Triphenylvinylphenyl substituted [2.2]paracyclophane-1,9-diene was successfully prepared by the Suzuki-Miyaura cross-coupling reaction of 4-bromo substituted [2.2]paracyclophane-1,9-diene and 4,4,5,5-tetramethyl-2-(4-(1,2,2-triphenylvinyl)phenyl)-1,3,2-dioxaborolane using Pd(OAc)2 as a catalyst, S-Phos as a ligand and K3PO4 as a base. The structures of bromo substituted [2.2] paracyclophane-1,9-diene and triphenylvinylphenyl substituted [2.2]paracyclophane-1,9-diene were fully characterized by 1H NMR spectroscopy and X-ray crystallography. 4-Triphenylvinylphenyl substituted [2.2]paracyclophane-1,9-diene exhibited aggregation-induced emission characteristics when the water fraction was higher than 80% in the THF/water mixtures. 4-Triphenylvinylphenyl substituted [2.2]paracyclophane-1,9-diene displays much higher fluorescence when the water fraction is 90% compared to that of model compounds due to both through bond and through space conjugation. To the best for our knowledge, we are the first to synthesize triphenylvinylphenyl substituted [2.2]paracyclophane-1,9-diene with aggregation-induced emission characteristics.

| S-EPMC9080709 | biostudies-literature

Aggregation-induced emission and aggregation-promoted photochromism of bis(diphenylmethylene)dihydroacenes.

Project description:Reported herein is a new class of pure polycyclic hydrocarbon molecules, designed through a novel aggregation-induced emission (AIE) strategy, with unexpected photochromic properties. The restriction of intramolecular motion was found as a comprehensive mechanism for the AIE effect. The photochromism mechanism study revealed that the photocyclization reaction of cis-stilbene, the molecular conformation in the single crystal and the tetracene backbone should contribute to the unique photo behavior. In particular, the fast responsive, photo-reversible and thermo-irreversible photochromic effect facilitated in the solid state opens a new field of aggregation-promoted photochromism.

| S-EPMC5500900 | biostudies-literature

Fluorescent Bis-Calix[4]arene-Carbazole Conjugates: Synthesis and Inclusion Complexation Studies with Fullerenes C60 and C70.

Project description:Supramolecular chemistry has become a central theme in chemical and biological sciences over the last decades. Supramolecular structures are being increasingly used in biomedical applications, particularly in devices requiring specific stimuli-responsiveness. Fullerenes, and supramolecular assemblies thereof, have gained great visibility in biomedical sciences and engineering. Sensitive and selective methods are required for the study of their inclusion in complexes in various application fields. With this in mind, two new fluorescent bis-calix[4]arene-carbazole conjugates (4 and 5) have been designed. Herein, their synthesis and ability to behave as specific hosts for fullerenes C60 and C70 is described. The optical properties of the novel compounds and their complexes with C60 and C70 were thoroughly studied by UV-Vis and steady-state and time-resolved fluorescence spectroscopies. The association constants (Ka) for the complexation of C60 and C70 by 4 and 5 were determined by fluorescence techniques. A higher stability was found for the C70@4 supramolecule (Ka = 5.6 × 104 M-1; ΔG = -6.48 kcal/mol). Evidence for the formation of true inclusion complexes between the host 4 and C60/C70 was obtained from NMR spectroscopy performed at low temperatures. The experimental findings were fully corroborated by density functional theory (DFT) models performed on the host-guest assemblies (C60@4 and C70@4).

| S-EPMC8399125 | 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