An effective method for synthesizing thiophene-containing fluorophores
Chemists from Ural Federal University (UrFU, Ekaterinburg) have suggested a new technique for synthesizing thiophene derivatives and studied their fluorescent properties experimentally as well as theoretically. Many organic compounds containing thiophene rings exhibit a significant pharmacological activity.
Thanks to their unusual electronic nature and low aromaticity, thiophenes are an ideal molecule for synthesizing photoactive polymers, liquid crystals, and organic dyes for solar cells. The researchers described their discovery on the pages of the Chemistry - An Asian Journal.
A research group from the UrFU Institute of Chemical Engineering, in collaboration with an Italian scientist (Scuola Normale Superiore, Pisa; present affiliation, Nazarbaev University, Astana, Kazakhstan), has published the results of a joint research, showing a new, convenient, and effective two-step procedure for producing new thiophene derivatives from simple and easy to obtain starting materials.
They have determined the features of the mechanism of this reaction using quantum mechanical calculations to compute the reaction thermodynamic parameters, as well as to compare the electronic structure of active centers, to plot the structure of intermediate substances, and to investigate their intramolecular interactions.
The proposed method is promising due to its safe reaction conditions, suggesting that this protocol may provide a valid alternative to previously reported protocols, which are tedious, time consuming, and result in poor yields using dangerous harsh conditions. Moreover, the new procedure can be used to synthetize libraries of new thiophene derivatives, whose structures will include new combinations of substituents, depending on the requirements of specific applications.
The compounds obtained possess important photophysical properties, in particular fluorescence (the emission of light by a substance that has absorbed light or other electromagnetic radiation). Molecules and materials with fluorescent properties are of great interest to the field of organic photonics, when creating luminescent (OLEDs and displays, luminescent probes and labels) and photovoltaic devices (photodetectors, color-sensitized solar cells).
State-of-the-art quantum mechanical methods were used to interpret the experimental results and study the characteristics of the ground and excited states of these new compounds. Due to their photophysical properties and sensitivity to the environment, these synthesized compounds may found applications in many areas, especially in biology, because of their structural similarity with biologically active thiophenes.
The article published in the Chemistry - An Asian Journal is the fourth paper published in 2017 by the team of chemists from UrFU and dedicated to new heterocyclic fluorophores. Previously, they developed a procedure for synthesizing 2-aryl-1,2,3-triazoles, as well as discovered and studied their fluorescent properties. In addition, they have proposed a new technique for the synthesis of 4,5-dihydro-1,2,4-triazoles and showed that such qualities as accessibility, synthetic simplicity, stability and high sensitivity to the microenvironment make these compounds a convenient platform for creating new sensors.
The editorial staff of the European Journal of Organic Chemistry noted the subsequent article about synthesis and fluorescent properties of di- and trisubstituted thiazoles as very important. In each publication, new and original substances are presented, which also have unusual optical properties in solution, solid crystalline state, or suspension (nanoparticles).
Based on the results obtained, the researchers prepare to proceed to designing, synthesizing and investigating the fluorescent properties of compounds that are promising candidates for practical use in biology or medicine.
"Our work would not be possible without the funding we received under the UrFU development program and the competitiveness enhancement program (UrFU is a participant in the 5-100 Project). In conference on organic chemistry, we met the theoretical physicist Enrico Benassi, who became an important member of our team. In order to measure the fluorescence spectra and determine the optical characteristics of synthesized compounds, we had to travel to other institutes in Russia and even to the Nankai University (China).
Concrete and effective results appeared only when our institute has purchased new high quality equipment (a UV spectrophotometer and two Japanese fluorimeters). Thanks to this equipment, our studies have reached the world-level quality and importance of the problems being solved in them, and we have managed to produce publications with high impact factor", - says the lead author of the articles, Dr. Nataliya Belskaya, Doctor of Chemistry.
Marina Sannikova | EurekAlert!
Scientists uncover the role of a protein in production & survival of myelin-forming cells
19.07.2018 | Advanced Science Research Center, GC/CUNY
NYSCF researchers develop novel bioengineering technique for personalized bone grafts
18.07.2018 | New York Stem Cell Foundation
A new manufacturing technique uses a process similar to newspaper printing to form smoother and more flexible metals for making ultrafast electronic devices.
The low-cost process, developed by Purdue University researchers, combines tools already used in industry for manufacturing metals on a large scale, but uses...
For the first time ever, scientists have determined the cosmic origin of highest-energy neutrinos. A research group led by IceCube scientist Elisa Resconi, spokesperson of the Collaborative Research Center SFB1258 at the Technical University of Munich (TUM), provides an important piece of evidence that the particles detected by the IceCube neutrino telescope at the South Pole originate from a galaxy four billion light-years away from Earth.
To rule out other origins with certainty, the team led by neutrino physicist Elisa Resconi from the Technical University of Munich and multi-wavelength...
For the first time a team of researchers have discovered two different phases of magnetic skyrmions in a single material. Physicists of the Technical Universities of Munich and Dresden and the University of Cologne can now better study and understand the properties of these magnetic structures, which are important for both basic research and applications.
Whirlpools are an everyday experience in a bath tub: When the water is drained a circular vortex is formed. Typically, such whirls are rather stable. Similar...
Physicists working with Roland Wester at the University of Innsbruck have investigated if and how chemical reactions can be influenced by targeted vibrational excitation of the reactants. They were able to demonstrate that excitation with a laser beam does not affect the efficiency of a chemical exchange reaction and that the excited molecular group acts only as a spectator in the reaction.
A frequently used reaction in organic chemistry is nucleophilic substitution. It plays, for example, an important role in in the synthesis of new chemical...
Optical spectroscopy allows investigating the energy structure and dynamic properties of complex quantum systems. Researchers from the University of Würzburg present two new approaches of coherent two-dimensional spectroscopy.
"Put an excitation into the system and observe how it evolves." According to physicist Professor Tobias Brixner, this is the credo of optical spectroscopy....
13.07.2018 | Event News
12.07.2018 | Event News
03.07.2018 | Event News
20.07.2018 | Power and Electrical Engineering
20.07.2018 | Information Technology
20.07.2018 | Materials Sciences