BORON PHOTOCHEMISTRY XIV. THE DIMESITYLBORYL GROUP AS AN AUXOCHROME IN DYES: THE SYNTHESIS OF para-SUBSTITUTED DIMESITYLBORYLPHENYLAZONAPHTHOL DYES

Article abstract of DOI:10.1016/S0022-328X(00)83994-7

The dimesitylboryl group is a new auxochrome.This group was evaluated by comparison of 4--1-naphthol (III) with 4--1-naphthol (IV) and of the substituted N-<5-hydroxy-8-(4-dimesitylborylphenylazo)naphthyl>-1,3-benzenedisulfonamide (VIIIa) with N-<5-hydroxy-8-(4-nitrophenylazo)naphthyl>-1,3-benzenedisulfonamide (VIIIb).The syntheses of 5-hydroxy-8-(4-dimesitylborylphenylazo)-1-naphthyl amine (IX) and α-<3-(4-dimesitylborylphenylazo)-4-hydroxynaphthoxy>propionic acid (X) are reported.The visible spectra of the dimesitylboryl-containing dyes and those of the nitro analogs were similar in shape.The spectral shifts of the dimesitylboryl compounds are as great as those of the corresponding nitro analogs.However, the boryl-substituted dyes required a nondonor medium for alkalinity-induced spectral shifts.As an auxochrome the dimesitylboryl group is roughly equivalent to a nitro group.