Jacek Doskocz

Practical synthesis of bis-substituted tetrazines with two pendant 2-pyrrolyl or 2-thienyl groups, precursors of new conjugated polymers

Abstract Novel linear oligoheterocycles based on substituted tetrazines are described. The desired compounds have been accomplished by a variation of the original Pinner [Ann. Chem., 297 (1897) 221] synthesis in which the aromatic nitrile reacted with hydrazine in an aqueous solution to give bis(pyrrolyl)tetrazines or bis(phenyl)tetrazines. The bis(phenyl)tetrazines reacted with 3,4-ethylenedioxy-2-(trimethyltin)thiophene or 2-(trimethyltin)thiophene in the presence of Pd(PPh3)2Cl2 or Pd(PPh3)4 as catalyst to give the desired compounds. Quantum-chemical calculations were performed to assess the usefulness of the synthesized compounds for electropolymerization. Studies have indicated qualitative difference between bis-pyrrole tetrazine and bis-phenyl tetrazines regarding the electronic density rearrangement due to the loss of an electron.

CONVENIENT SYNTHESIS AND PHYSICOCHEMICAL PROFILE OF NEW DERIVATIVES OF PYRIMIDINE

A synthesis of linear oligoheterocycles based on the substituted pyrimidines are described. The desired compounds have been accomplished by the variation of the original Pinner synthesis in which the aliphatic nitrile reacted with hydrogen chloride to give imino ester. These compound reacted with ammonia gas to give amidine. Chalcones in reaction with amidines give bis(phenyl)pyrimidines. The bis(phenyl)pyrimidines reacted with 3,4- ethylenedioxy-2-trimethyltinthiophene or 2-trimethyltinthiophene in the presence of Pd(PPh3)2Cl2 or Pd(PPh3)4 as catalyst to give designed compounds. In this work are presented also some electrochemical measurements using Langmuir - Blodgett technique in mono- and binary systems.

Functionalized Phenothiazine and Carbazole Chromophores: Synthesis and Characterization

Synthesis, characterization, and photophysical properties for a few optical chromophores are reported. Phenothiazine and carbazole units played an important role to contribute high electron donability and connect the resonance pathway via conjugate effect in the cyclized ring besides the aromatic ring. Theoretical calculations and an absorption spectroscopic study gave useful information about the energy states and structures of chromophores.