7265-22-7Relevant academic research and scientific papers
Synthesis of Symmetric Binuclear 5,6-Dihydro-1,2,4,5-tetrazinium Perchlorates
Asfandeev, A. Yu.,Burtasov, A. A.,Idris, T. D.,Kostryukov, S. G.,Kozlov, A. Sh.,Krasnov, D. A.,Petrov, P. S.,Tezikova, V. S.
, p. 614 - 620 (2021/06/02)
Abstract: A series of 3,3′-(1,4-phenylene)bis(1-4-R-phenyl)-5-phenyl-5,6-dihydro-1,2,4,5-tetrazinium) perchlorates (R = H, Me, Cl, OMe, CN, NO2) were obtained as a result of a three-stage synthesis from terephthalic aldehyde. The synthesis of tetrazinium salts was carried out by reaction of the corresponding formazans with formalin in the presence of perchloric acid in dioxane. Formazans and tetrazinium perchlorates were isolated in individual state and characterized by elemental analysis, IR, UV, 1H, and 13C NMR spectroscopy data. The process of electrochemical reduction of tetrazinium perchlorates was studied using the method of cyclic voltammetry (CV). It has been shown that these compounds are perspective precursors of symmetric biradical systems based on verdazyl radicals.
Synthesis and characterization of conjugated/cross-conjugated benzene-bridged boron difluoride formazanate dimers
Barbon, Stephanie M.,Price, Jacquelyn T.,Yogarajah, Umesh,Gilroy, Joe B.
, p. 56316 - 56324 (2015/07/15)
One of the most common strategies for the production of molecular materials with optical properties in the far-red/near-IR regions of the electromagnetic spectrum is their incorporation into dimeric architectures. In this paper, we describe the synthesis and characterization (1H, 11B, 13C and 19F NMR spectroscopy, IR and UV-vis absorption and emission spectroscopy, mass spectrometry and X-ray crystallography) of the first examples of boron difluoride (BF2) formazanate dimers. Specifically, the properties of meta- and para-substituted benzene-bridged dimers p-10 and m-10 were compared to closely related boron difluoride triphenyl formazanate complex 11 in order to assess the effect of electronic conjugation and cross conjugation on their light absorption/emission and electrochemical properties. While the properties of cross-conjugated dimer m-10 did not differ significantly from those of monomer 11, conjugated dimer p-10 exhibited red-shifted absorption and emission maxima and was easier to reduce electrochemically to its bis radical anion and bis dianion form compared to monomer 11. Both dimers are weakly emissive in the far-red/near-IR and exhibited large Stokes shifts (>110 nm, 3318 cm-1). Unlike a closely related para-substituted benzene-bridged boron dipyrromethene (BODIPY) dimer, the emission quantum yields measured for the BF2 formazanate dimers exceeded those observed for monomeric analogues.
