Oxadisilole-fused 9-aminoacridines and 12-aminobenzo[b]acridines have been synthesized by the nucleophilic addition and 1,5-hydrogen shift reaction of arynes with 2-aminobenzonitriles in good yield at room temperature. Dioxatrisilole-fused 9-aminoacridines have also been obtained. The photophysical, redox, and thermal properties of these compounds have been determined. The oxadisilole-fused 9-aminoacridines show potential for use as blue emitters for OLED applications, because of their high fluorescence quantum yields and good thermal stabilities. The proposed mechanism was also studied. Theoretical calculations on the HOMO and LUMO values of these compounds were performned.

Oxadisilole-fused 1H-benzo[f]- and 1H-naphtho[2,3-f]indazoles have been synthesized by the 1,3-dipolar cycloaddition reactions of benzo- or naphtho-oxabicycloalkenes with nitrile imines generated in situ from N-arylhydrazonoyl chlorides followed by deoxygenation and aromatization. The photophysical, redox and thermal properties of these compounds have been characterized. Some of the indazoles show potential as deep-blue emitters for OLED applications as a result of their high fluorescence quantum yields and good thermal stabilities.

Oxadisilole-fused benzisoxazoles or naphthisoxazoles were obtained through 1,3-dipolar cycloaddition of arynes with nitrile oxides in good yields at room temperature. Key to the procedure is the simultaneous in situ generation of reactive nitrile oxides from arenecarbohydroximoyl chlorides and aryne reactants from benzobis(oxadisilole) or 2,3-naphthoxadisilole. One oxadisilole-fused benzisoxazole is a new precursor of a benzyne formed by a phenyliodination/fluoride-induced elimination protocol. By using this benzyne, cycloadducts were synthesized in good yields. The de-oxadisilole reaction of some of the oxadisilole-fused benzisoxazoles could be easily conducted with a 1.0 M solution of tetrabutylammonium fluoride in THF at room temperature.

The fluorine-containing trans-1,2-cyclopropane derivatives 4ba–4dd were synthesized from the fluorine-containing electron-deficient alkenes 3a–3d with semistabilized arsonium ylides 2b–2d, in biphasic system of dichloromethane-50% aqueous sodium hydroxide, generated in situ from the corresponding arsonium salts 1b–1d at room temperature in good yields with high stereoselectivity. The structure of fluorine-containing trans-1,2-cyclopropane derivatives were also studied.