Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 72, Issue 21, Pages 8070-8075Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo7015357
Keywords
-
Categories
Ask authors/readers for more resources
[GRAPHICS] 2,3,6,7-Tetrabromonaphthalene dianhydride has been synthesized by the bromination of naphthalene dianhydride with dibromoisocyanuric acid in excellent yield. The condensation of this dianhydride with 2,6-diisopropylaniline yielded the corresponding tetrabromo-substituted naphthalene diimide (NDI), which is a versatile precursor for the synthesis of core-tetrafunctionalized NDIs. Nucleophilic substitution of tetrabromo NDI with alkoxy, alkylthio, and alkylamino nucleophiles afforded a series of core-tetrasubstituted NDI chromophores that complete the series of previously reported di- and trifunctionalized NDI derivatives. The effects of electronic nature and number of core substituents on the optical and electrochemical properties of NDIs have been investigated by UV-vis and fluorescence spectroscopy and cyclic voltammetry. The absorption maxima (629-642 nm) of tetraamino NDIs are strongly bathochromically shifted compared to those of other core-functionalized NDIs.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available