10.1016/S0040-4039(00)84435-4
The research aimed to develop new electron donors by synthesizing three 3,4-dichalcogen-bridged fluoranthenes, with the donor strength increasing in the order of the chalcogen triad: sulfur, selenium, and tellurium. The study focused on polycyclic aromatic compounds with peri-dichalcogen bridges, which are known for their electron-donating properties. The researchers synthesized fluorantheno[3,4-cdl-1,2-dithiole], -diselenole, and -ditellurole, using a multistage pathway starting with acenaphthene and involving various chemical reactions such as chlorination, dehydrogenation, bromination, and Diels-Alder reactions. The synthesized compounds were characterized by elemental and spectroscopic analyses, and their electronic spectra and cyclic voltammetry results indicated an enhanced electronic interaction between the fluoranthene and the heavy chalcogen, which strengthened the donor character.
10.1021/jo00206a017
The study investigates the synthesis and spectroscopic properties of a series of para-substituted Se-phenyl selenobenzoates. The researchers synthesized eleven compounds, including NO2, CN, C(O)CH3, C(O)OCH2CH3, F, Cl, Br, CH3, OCH3, and N(CH3)2 as substituents. The primary goal was to systematically evaluate the 77Se and 13C NMR chemical shifts, coupling constants, and infrared carbonyl absorption frequencies of these compounds. The study found that mesomeric substituents strongly interact with the aromatic ring, and the SeC(0)Ph moiety is electron-deficient relative to the substituted benzene. The results provide valuable data for understanding the electronic effects of various substituents on selenol esters, which is crucial for further applications in biomolecular studies involving selenium.