jo9b00468_si_002.cif (823.6 kB)
1,3-Diylideneisoindolines: Synthesis, Structure, Redox, and Optical Properties
dataset
posted on 2019-04-25, 00:00 authored by Yuriy
V. Zatsikha, Briana R. Schrage, Julia Meyer, Victor N. Nemykin, Christopher J. ZieglerDiiminoisoindoline
(DII) is a crucial reagent for the synthesis
of phthalocyanine as well as related macrocycles and chelates such
as hemiporphyrazine and bis(iminopyridyl)isoindoline. In this report,
we present the synthesis and characterization of four 1,3-diylideneisoindolines
prepared via the reaction of several organic CH acids and DII. These
orange or red compounds exhibit intense π → π*
transitions in the UV–visible region. The redox properties
and electronic structures of all new compounds were investigated using
cyclic voltammetry and density functional theory (DFT). The observed
electrochemistry and UV–visible transitions are in good agreement
with the DFT and time-dependent DFT calculations, which indicate that
the HOMO is largely centered at the OC–C–CO
fragments, and the lowest unoccupied molecular orbital is more extended
onto the isoindoline unit.