WFIGR ID=jo7015357n00002> |
2,3,6,7-Tetrabromonaphthalene dianhydride has been synthesized by the bromination of naphthalenedianhydride
with dibromoisocyanuric acid in excellent yield. The condensation of this dianhydride
with2,6-diisopropylaniline yielded the corresponding tetrabromo-substituted naphthalene diimide (NDI),
whichis a versatile precursor for the synthesis of core-tetrafunctionalized NDIs. Nucleophilic substitution oftetrabromo NDI
with alkoxy, alkylthio, and alkylamino nucleophiles afforded a series of core-tetrasubstituted NDI chromophores that complete the series of previously reported di- and trifunctionalizedNDI derivatives. The effects of electronic nature and number of core substituents on the optical andelectrochemical properties of NDIs have been investigated by UV-vis and fluorescence spectroscopyand cyclic voltammetry. The absorption maxima (629-642 nm) of tetraamino NDIs are stronglybathochromically shifted compared to those of other core-functionalized NDIs.
