Abstract:
A series of soluble aryloxy-substituted tetraphenylethylenes (A-D) were synthesized by a reaction of p-chlorophenol, phenol, p-methylphenol or p- methoxyphenol with tetrakis(4-bromophenyl)ethylene in excellent overall
yields. Preliminary electrochemical studies showed that these molecules
undergo reversible oxidation and form stable cation radical salt. Furthermore, a plot of oxidation potentials of A-D against the Hammett
constants of aryloxy substituents showed a linear dependence and thus
establishing effective electronic coupling of the aryloxy substituents with tetraphenylethylene (TPE) core. A similar strategy was then employed for
the preparation of two generations using phloroglucinol as branching
of TPE-core dendrimers (G1 and G2) units. The branching units in these
dendrimers showed effective electronic coupling with the TPE core in the preliminary electrochemical studies. Efforts are underway to prepare higher generation dendrimers G3 and G4.
