Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Synthesis and properties of fluorescent 4'-azulenyl-functionalized 2,2':6',2?-terpyridines.

ABSTRACT: 4'-Azulenyl-substituted terpyridines were efficiently synthesized following the Kröhnke methodology via azulenylchalcone intermediates. These azulenyl-containing terpyridines showed fluorescent emission with a fluorescence quantum yield varying from 0.14, in the case of parent terpyridine, to 0.64 when methyl groups are grafted on the azulenyl seven-membered ring. According to the crystal structures and TDDFT calculations, different twisting of the aromatic constituents is responsible for the observed fluorescent behavior. The electrochemical profile contains one-electron oxidation/reduction steps, which can only be explained on the basis of the redox behavior of the azulene unit. The ability of the 4'-azulenyl 2,2':6',2?-terpyridine to bind poisoning metal cations was studied by UV-vis titrations using aqueous solutions of Hg(II) and Cd(II) chlorides as illustrative examples.

SUBMITTER: Ion AE

PROVIDER: S-EPMC5082674 | biostudies-other | 2016

REPOSITORIES: biostudies-other

ACCESS DATA

Json Xml

Publications

Synthesis and properties of fluorescent 4'-azulenyl-functionalized 2,2':6',2″-terpyridines.

Ion Adrian E AE Cristian Liliana L Voicescu Mariana M Bangesh Masroor M Madalan Augustin M AM Bala Daniela D Mihailciuc Constantin C Nica Simona S

Beilstein journal of organic chemistry 20160811

4'-Azulenyl-substituted terpyridines were efficiently synthesized following the Kröhnke methodology via azulenylchalcone intermediates. These azulenyl-containing terpyridines showed fluorescent emission with a fluorescence quantum yield varying from 0.14, in the case of parent terpyridine, to 0.64 when methyl groups are grafted on the azulenyl seven-membered ring. According to the crystal structures and TDDFT calculations, different twisting of the aromatic constituents is responsible for the ob ...[more]

PMID: 27829888

Similar Datasets

Synthesis of dye/fluorescent functionalized dendrons based on cyclotriphosphazene.

Project description:Functionalized phenols based on tyramine were synthesized in order to be selectively grafted on to hexachlorocyclotriphosphazene, affording a variety of functionalized dendrons of type AB(5). The B functions comprised fluorescent groups (dansyl) or dyes (dabsyl), whereas the A function was provided by either an aldehyde or an amine. The characterization of these dendrons is reported. An unexpected behaviour of a fluorescent and water-soluble dendron based on dansyl groups in mixtures of dioxane/water was observed.

| S-EPMC3252861 | biostudies-other

Anthracene functionalized terpyridines - synthesis and properties.

Project description:The synthesis of several symmetrically 4,4''-functionalized 2,2':6',2''-terpyridines is reported. In addition to the biscarboxylic acid 4,4''-tpy(CO₂H)₂ (3), the anthryl esters 4,4''-tpy(CO₂CH₂Anth) ₂(5a) and 4,4''-tpy(CO₂CH₂CH₂OAnth)₂ (5b) were synthesized. Furthermore, both anthryl esters were used to synthesize symmetric iron(II)-bis(terpyridine)complexes 6a-b. Irradiation experiments were carried out with both the free ligands and an iron(II)-complex in order to investigate the photochemistry of the compounds.

| S-EPMC2900913 | biostudies-literature

Pyrene-Functionalized Fluorescent Nanojars: Synthesis, Mass Spectrometric, and Photophysical Studies.

Project description:Nanojars are a class of supramolecular coordination complexes based on pyrazolate, Cu2+, and OH- ions that self-assemble around highly hydrophilic anions and serve as efficient anion binding and extraction agents. In this work, the synthesis, characterization, and photophysical properties of pyrene-functionalized fluorescent nanojars are presented. Three pyrene derivatives, 4-(pyren-1-yl)pyrazole (HL1), 4-(5-(pyren-1-yl)pent-4-yn-1-yl)pyrazole (HL2), and 4-(3-(pyrazol-4-yl)propyl)-1-(pyren-1-yl)-1,2,3-triazole (HL3), and the corresponding nanojars were synthesized and characterized using nuclear magnetic resonance spectroscopy and mass spectrometry. Electronic absorption, steady-state, and time-resolved fluorescence measurements were carried out to understand the interaction between the pyrene fluorophore and copper nanojars. Optical absorption measurements have shown minor ground state interaction between the fluorophore and nanojars. The fluorescence of pyrene is significantly quenched when attached to nanojars, suggesting strong contribution from the paramagnetic Cu2+ ions. Significant static quenching is observed in the case of L1, when pyrene is directly bound to the nanojar, whereas in the case of L2 and L3, when pyrene is attached to the nanojars using flexible tethers, both static and dynamic quenching are observed.

| S-EPMC8656208 | biostudies-literature

Synthesis and Properties of Bridgehead-Functionalized Permethylbicyclo[2.2.2]octasilanes.

Project description:A series of previously unknown bridgehead-functionalized bicyclo[2.2.2]octasilanes, Me3Si-Si8Me12-X, X-Si8Me12-X, and X-Si8Me12-Y [X, Y = -SiMe n Ph3-n (n = 1, 2) (2, 3, 10), -SiMe2Fc (Fc = ferrocenyl) (4, 11, 13, 14), -COR (R = Me, tBu) (6, 7, 12), COOMe (8), COOH (9)], have been prepared by the reaction of the silanides Me3Si-Si8Me12-K+ or K+-Si8Me12-K+ with proper electrophiles and fully characterized. The molecular structures of 2, 3, 4, 6, 8, 9, 10, and 13 as determined by single-crystal X-ray diffraction analysis exhibit a slightly twisted structure of the bicyclooctasilane cage. Endocyclic bond lengths, bond angles, and dihedral angles are not influenced considerably by the substituents attached to the bridgehead silicon atoms. Due to σ(SiSi)/π(aryl) conjugation, a 20-30 nm bathochromic shift of the longest wavelength UV absorption band relative to Me3Si-Si8Me12-SiMe3 (1) is evident in the UV absorption spectra of the phenyl and ferrocenyl derivatives. Otherwise, UV absorption data do not support the assumption of aryl/aryl or aryl/C=O interaction via the σ(SiSi) bicyclooctasilane framework.

| S-EPMC3755819 | biostudies-literature

Synthesis of highly functionalized 2,2'-bipyridines by cyclocondensation of β-ketoenamides - scope and limitations.

Project description:The scope of a flexible route to unsymmetrically functionalized bipyridines is described. Starting from 1,3-diketones 1a-e, the corresponding β-ketoenamines 2a-e were converted into different β-ketoenamides 3a-g by N-acylation with 2-pyridinecarboxylic acid derivatives. These β-ketoenamides were treated with a mixture of TMSOTf and Hünig's base to promote the cyclocondensation to 4-hydroxypyridine derivatives. Their immediate O-nonaflation employing nonafluorobutanesulfonyl fluoride provided the expected 4-nonafloxy-substituted bipyridine derivatives 5a-g in moderate to good overall yields. The bipyridyl nonaflates are excellent precursors for palladium-catalyzed reactions as demonstrated by representative Suzuki and Sonogashira couplings. Thus, a library of specifically substituted bipyridine derivatives was generated, showing the versatility of the simple 1,3-diketone-based approach to this important class of ligands.

| S-EPMC4979911 | biostudies-literature

Synthesis and Fluorescent Properties of Novel Isoquinoline Derivatives.

Project description:Isoquinoline derivatives have attracted great interest for their wide biological and fluorescent properties. In the current study, we focused on the synthesis of a series of novel isoquinoline derivatives substituted at position 3 of the heteroaromatic ring. Compounds were obtained in a Goldberg-Ullmann-type coupling reaction with appropriate amides in the presence of copper(I) iodide, N,N-dimethylethylenediamine (DMEDA), and potassium carbonate. The structures of novel isoquinolines were confirmed by IR, NMR, and elemental analysis, as well as X-ray crystallography. In the course of our research work, the visible fluorescence of this class of compounds was observed. The above findings prompted us to investigate the optical properties of the selected compounds.

| S-EPMC6891638 | biostudies-literature

Novel Fluorescent Azacyanine Compounds: Improved Synthesis and Optical Properties.

Project description:Benzothiazoles are known to possess a number of biological activities and therefore are considered to be an important scaffold in the design and synthesis of pharmacophores. In this study, an improved synthesis method for novel fluorescent benzothiazole-based cyclic azacyanine (CAC) dyes bearing different electron-donating/withdrawing groups on their scaffold is presented. The improved method enabled us to increase the synthesis yield for the previously reported CACs. More importantly, it allowed us to synthesize new CAC dyes that were not synthesizable with the previously reported method. The synthesized dyes were characterized by 1H and 13C NMR spectroscopy, elemental analysis, and mass spectrometry and their optical (absorption and fluorescence) properties were investigated. All of the synthesized CACs were found to be displaying strong absorption within the range of 387-407 nm. The spectral shifts observed in the absorption and fluorescence measurements suggested that the spectroscopic and optical properties of CACs can be directly modulated by the nature of the electron-donating/withdrawing substituents. The fluorescence quantum yields (QYs) of the unsubstituted (parent CAC) and substituted CACs were also measured and compared. The fluorescence QY of CACs with electron-donating substituents (methoxy or ethoxy) was found to be at least four times higher than that of the parent CAC with no substitutions.

| S-EPMC7495752 | biostudies-literature

Bio-Derived Fluorescent Carbon Dots: Synthesis, Properties and Applications.

Project description:The transformation of biowaste into products with added value offers a lucrative role in nation-building. The current work describes the synthesis of highly water-soluble, luminous carbon quantum dots (CQDs) in the size range of 5-10 nm from discarded rice straw. The small spherical CQDs that were formed had outstanding optical and luminescent qualities as well as good photostabilities. By performing quantitative multi-assay tests that included antioxidant activities, in vitro stability and colloidal assay investigations as a function of different CQD concentrations, the biocompatibility of CQDs was evaluated. To clearly visualize the type of surface defects and emissive states in produced CQDs, excitation-dependent fluorescence emission experiments have also been carried out. The "waste-to-wealth" strategy that has been devised is a successful step toward the quick and accurate detection of Cu2+ ion in aqueous conditions. The fluorescence-quenching behavior has specified the concentration dependency of the developed sensor in the range of 50 μM to 10 nM, with detection limit value of 0.31 nM. The main advantage of the current research is that it offers a more environmentally friendly, economically viable and scaled-up synthesis of toxicologically screened CQDs for the quick fluorescence detection of Cu2+ ions and opens up new possibilities in wastewater management.

| S-EPMC9416149 | biostudies-literature

Facile One-Pot Synthesis of Functionalized Quinoline-Fused Fluorescent Dihydro/Spiro-quinazolinone Derivatives.

Project description:A facile and efficient method has been developed for the synthesis of quinoline-fused fluorescent dihydro/spiro-quinazolinones. A plausible mechanism involving an acid-mediated enaminone intermediate is provided. The reaction proceeded using p-toluene sulfonic acid as a green promoter. The methodology was successful in synthesizing various quinoline-appended spiro-quinazolinones 4a-o. The synthetic utility of compounds 4a-o was demonstrated by synthesizing compounds 6a-d via Suzuki coupling as a key reaction. Significantly, the π-π* electronic transition of compounds 4c and 4k showed a blue shift. The molar extinction coefficient (ε), Stoke's shift (Δu̅), and quantum yield (Φf)c were calculated for these derivatives (4c and 4k).

| S-EPMC9219092 | biostudies-literature

Synthesis and properties of sulfur-functionalized triarylmethylium, acridinium and triangulenium dyes.

Project description:Triangulenium dyes functionalized with one, two or three ethylthiol functionalities were synthesized and their optical properties were studied. The sulfur functionalities were introduced by aromatic nucleophilic substitution of methoxy groups in triarylmethylium cations with ethanethiol followed by partial or full ring closure of the ortho positions with nitrogen or oxygen bridges leading to sulfur-functionalized acridinium, xanthenium or triangulenium dyes. For all the dye classes the sulfur functionalities are found to lead to intensely absorbing dyes in the visible range (470 to 515 nm), quite similar to known analogous dye systems with dialkylamino donor groups in place of the ethylthiol substituents. For the triangulenium derivatives significant fluorescence was observed (?f = 0.1 to ?f = 0.3).

| S-EPMC6753677 | 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