Krzysztof R. Idzik

Charged States of 1,3,5-Triazine Molecules as Models for Star-shaped Molecular Architecture: A DFT and Spectroelectrochemcial Study

The density functional theory calculations of molecular structure and spectroscopic and electronic properties of charged states in four triazine-heteroaryl star-shaped compounds are presented. The molecules end-capped with different heteroaryl groups, i.e., thiophene (TTT1), furan (TFT2), 3,4-ethylenedioxythienyl (TET3), and thiazole (TSNT4), were studied by electrochemical and in situ ESR/UV-vis-NIR spectroelectrochemical techniques in tetrahydrofuran/(TBA)BF(4). The charged states of monomers were created by cathodic reduction and the stability of generated anion radicals was characterized in detail both experimentally and theoretically. The TET3 molecule resulted in a star-shaped hyperbranched polymer formed anodically which in turn can be reversibly oxidized up to the tetracation. The nature and charge distribution of charge carriers at each redox state in the as-prepared polymer was clarified by calculations for the model (TET3)(3) trimer structure.

Synthesis and Optical Properties of Various Thienyl Derivatives of Pyrene

A series of various thienyl derivatives of pyrene were synthesized by Stille cross-coupling procedure. Their structures were characterized by 1H NMR, 13C NMR and elemental analysis. The spectroscopic characteristics were investigated by UV–vis absorption and fluorescence spectra. Based on quantum chemical calculations, the energy levels of investigated molecules with respect to the pyrene molecule were also discussed.

A New Route to Light Emitting Organic Materials Based on Triazine Derivatives

Novel light-emitting organic materials comprising conjugated oligomers chemically attached via a flexible spacer to an electron–or hole-conducting core were synthesized by Stille cross-coupling methodology and designed for tunable charge injection and optical properties. The hyperbranched structures have been characterized by 1H NMR, 13C NMR, and UV-VIS spectroscopy. The obtained structures show good stability in common organic solvents such as CHCl3, toluene, and CH2Cl2 and exhibit excellent thermal stability. A preliminary electroluminescence properties were also investigated. This class of materials will help to balance charge injection and transport and to spread out the charge recombination zone, thereby significantly improving the device efficiency and lifetime of unpolarized and polarized OLEDs.

On the Electrochemistry and Spectroelectrochemistry of Small Model Star‐Shaped Compounds: 1,3,5‐Triaryl‐1‐Methoxybenzenes and 2,4,6‐Triaryl‐1,3,5‐Trimethoxybenzenes

Model structures of 1,3,5-triarylbenzenes with a substituted benzene core linked to thienyl or 3,4-ethylenedioxythienyl (EDOT) terminal groups are studied by electrochemical and in situ ESR/UV/Vis/NIR spectroelectrochemical techniques. Oxidative polymerization of the monomers results in C-C coupling of the thiophene moieties in the 5-position, forming dimeric structures with bithiophene linkers as the first step. Both the doubly charged protonated dimer and the new dimer formed after proton release are studied in detail for 2,4,6-tris[2-(3,4-ethylenedioxythienyl)]-1-methoxybenzene. Quite high stability of the doubly charged σ dimer formed on oxidation with unusual redox behavior at the electrode is observed. Density functional calculations of the molecular structure as well as spectroscopic and electronic properties of charged states in 1,3,5-triarylbenzene derivatives in the monomeric, dimeric, and oligomeric form are presented. The complex spectroelectrochemical response of a thin solid film formed on the electrode surface upon potentiodynamic polymerization indicates the existence of different charge states of oligomeric structures within the solid matrix.

Efficient Synthesis of Readily Water-Soluble Amides Containing Sulfonic Groups

Abstract A series of various readily water-soluble amides were synthesized by different procedures. These compounds are useful chemical tracers for assessing the cooling progress in a georeservoir during geothermal power plant operation. Acylation of primary amines was carried out by basically employing the Schotten–Baumann method. As a second method a single-phase solvent system consisting of ethyl acetate as an organic solvent and triethylamine as a catalyst was used. Products were characterized by 1H NMR and 13C NMR. [Supplementary materials are available for this article. Go to the publishers online edition of Synthetic Communications® for the following free supplemental resource(s): Full experimental and spectral details.] GRAPHICAL ABSTRACT

Efficient synthesis and reaction kinetics of readily water soluble esters containing sulfonic groups.

A series of various readily water soluble esters were synthesized by a very efficient procedure. These compounds can be useful as thermosensitive tracers for studying the cooling progress in a low enthalpy georeservoir exploitable by double flash geothermal power plant systems. The kinetics of their hydrolysis was investigated. Acylation of primary alcohols or phenols was carried out by a method based on a single-phase solvent system consisting of ethyl acetate acting as an organic solvent and triethylamine acting as a catalyst. Products were characterized by 1H-NMR, and 13C-NMR.

Synthesis and sensing properties of a new carbazole fluorosensor for detection of abacavir

An abacavir-targeted fluorosensor based on the carbazole moiety has been synthesised and characterised. Recognition of abacavir is by base pairing between a uracil moiety present in the fluorosensor and the guanine moiety of abacavir. The fluorosensor exhibits five-fold quenching in the presence of 50 μM abacavir. Its sensitivity to abacavir is superior to that of other reverse transcriptase inhibitors: zidovudine, lamivudine and didanosine. Due to its high sensitivity, this fluorosensor has the potential to be used in multi-analyte array-based detection platforms as well as in microfluidics systems.

Efficient Synthesis of Readily Water-Soluble Sulfonic Acid Carbamates

A series of various readily water-soluble carbamates were synthesized with good yields. These compounds are useful chemical tracers for assessing the cooling progress in a georeservoir during geothermal power plant operation. Acylation of primary amines was carried out as well as using a solution of sodium bicarbonate and without the presence of salt. Products were characterized by 1H-NMR and 13C-NMR. Purity was confirmed through elemental analysis.

Synthesis by Stille Cross-Coupling Procedure and Electrochemical Characterization of Branched Polymers Based on Substituted 1,3,5-Triarylbenzenes

A series of various substituted 1,3,5-triarylbenzenes, 2,4,6-triaryl-1-phenoles, 1,3,5-triaryl-1-methoxybenzenes and 2,4,6-triaryl-1,3,5-trimethoxybenzenes were synthesized by a Stille cross-coupling procedure. Their structures were confirmed by 1H NMR, 13C NMR, and elemental analysis. Containing thienyl, furyl and EDOT groups polymers obtained in the process of electropolymerization could be carefully considered as a building material in a wide range of organic-electronic devices. We compare properties of monomers and related polymers depending on aryls moieties and their influence of hydroxyl and methoxyl groups attached to the central benzene core.

Molecular Recognition of the Antiretroviral Drug Abacavir: Towards the Development of a Novel Carbazole-Based Fluorosensor

Due to their optical and electro-conductive attributes, carbazole derivatives are interesting materials for a large range of biosensor applications. In this study, we present the synthesis routes and fluorescence evaluation of newly designed carbazole fluorosensors that, by modification with uracil, have a special affinity for antiretroviral drugs via either Watson–Crick or Hoogsteen base pairing. To an N-octylcarbazole-uracil compound, four different groups were attached, namely thiophene, furane, ethylenedioxythiophene, and another uracil; yielding four different derivatives. Photophysical properties of these newly obtained derivatives are described, as are their interactions with the reverse transcriptase inhibitors such as abacavir, zidovudine, lamivudine and didanosine. The influence of each analyte on biosensor fluorescence was assessed on the basis of the Stern–Volmer equation and represented by Stern–Volmer constants. Consequently we have demonstrated that these structures based on carbazole, with a uracil group, may be successfully incorporated into alternative carbazole derivatives to form biosensors for the molecular recognition of antiretroviral drugs.