Microwave-assisted synthesis and spectroscopic properties of novel pyridine-based fluorescent molecular probes

[EN] Fluorescent molecular probes become interesting analytical tools in determination and labeling of chemical compounds and physical properties such as viscosity and polarity. Currently known fluorescent molecular probes can selectively and regardless of the environment detect only few molecules, and applicability in determination of micro- viscosity and micro-polarity are limited to narrow range and specific condition, therefore design and synthesis of novel molecular probes with extended range of operation are highly needed [1]. Traditional synthesis of 2-amino-4,6-diphenyl-pyridine-3-carbonitrile’s requires two step reaction with long heating time or and toxic solvent. By application of microwave irradiation, reaction time can be firmly shortened with the same or higher efficiency [2]. Derivatives of 2-amino-4,6-diphenyl-pyridine-3-carbonitrile can find application in different fields of science. Depending on the structure of fluorophore, those compounds exhibit high sensitivity to changes in polarity and viscosity of environment, also concentration of specific cations, and pH can be determined by measuring of fluorescence spectrum.The authors are grateful to the Foundation for Polish Science (Warsaw, Poland) - Project REINTEGRATION (Contract No. REINTEGRATION/2016-1/4 – “Synthesis and photochemistry/photophysics studies of the intelligent luminescent molecular sensors for selective detection in biochemistry and chemistry”) for financial support of the FPT research. The authors also acknowledge the support of the PROM programme no. PPI/PRO/2018/1/00013/U/001 which is co-financed by the European Social Fund under the Knowledge Education Development Operational Programme.http://ocs.editorial.upv.es/index.php/AMPERE2019/AMPERE2019Fiedor, P.; Ortyl, J.; Galek, M. (2019). Microwave-assisted synthesis and spectroscopic properties of novel pyridine-based fluorescent molecular probes. Editorial Universitat Politècnica de València. 394-400. https://doi.org/10.4995/AMPERE2019.2019.9829OCS39440

Photochemical study of a new bimolecular photoinitiating system for vat photopolymerization 3D printing techniques under visible light

In this work, we presented a new bimolecular photoinitiating system based on 2-amino-4,6-diphenylpyridine-3-carbonitrile derivatives as visible photosensitizers of diphenyliodonium salt. Real-time FTIR and photo-DSC photopolymerization experiments with a cycloaliphatic epoxide and vinyl monomers showed surprisingly good reactivity of the bimolecular photoinitiating systems under UV-A, as well as under visible light sources. Steady-state photolysis, fluorescence experiments, theoretical calculations of molecular orbitals, and electrochemical analysis demonstrated photo-redox behavior as well as the ability to form initiating species via photo-reduction or photo-oxidation pathways, respectively. Therefore, the 2-amino-4,6-diphenylpyridine-3-carbonitrile derivatives were also investigated as a type II free-radical photoinitiator with amine. It was confirmed that the 2-amino-4,6-diphenylpyridine-3-carbonitrile derivatives, in combination with different types of additives, e.g., amine as a co-initiator or the presence of onium salt, can act as bimolecular photoinitiating systems for cationic, free-radical, and thiol-ene photopolymerization processes by hydrogen abstraction and/or electron transfer reactions stimulated by either near-UV or visible light irradiation. Finally, the 2-amino-4,6-diphenylpyridine-3-carbonitrile derivatives were selected for 3D printing rapid prototyping experiments. Test objects were successfully printed using purely cationic photosensitive resin, created on a 3D printer with a visible LED light source