Synthesis And Study On The Properties Of 2,2- Bis(substituted Phenoxy) Benzo(1,3)dioxole Derivatives

Sixteen 2,2-bis(substituted phenoxy)benzo[1,3]dioxole derivatives were additionally systhesized. They were differentified in three series of products accoding to the positions of substituents in phenoxy groups: 7 p-position products (including: Et, t-Bu, F, Cl, Br, CN and COMe), 5 m-position ones (CN, Cl, Me, OMe, NO2) and 4 o-position ones (CN, Cl, Me, OMe), and they were delibratively confirmed by 1H NMR,13C NMR,UV-vis,m.p. and HR-MS methods. Two crystals of these 2,2-bis(substituted phenoxy) benzodioxole[1,3] derivatives were also obtained by the solution method. we observed that some performance parameters (such as UV-vis spectroscopy parameters) of the total 15 target compounds have well related to the excited-state substituent constant of the substitutents in phenoxys. Through comparing the dihedral angle of two phenoxy in the six the crystal data of 2,2-Bis(substituted phenoxy)-benzo[1,3]dioxole derivatives, we observed that the molecular conformation of these compounds have close relationship to their electronic effect of substituents in the phenoxys, that is, the substituent electronic effect can be impacted by the change of the molecular structure through the ortho-carbonate-type structure, but with few exceptions. The reasonable explanation were afforded for corresponding results in the paper.