A straightforward
method for the synthesis of a series of hitherto
unknown 1-azapyrenes is reported, which relies on a combination of
Pd-catalyzed cross-coupling reactions with Brønsted acid-mediated
cycloisomerization reactions. The methodology is highly modular and
allows an efficient synthesis of various substituted products in high
yields. The structural, electrochemical, and photophysical properties
of 1-azapyrenes have been studied by ultraviolet–visible (UV–vis)
and fluorescence spectroscopies, cyclic voltammetry, and density functional
theory (DFT) calculations.
A new and convenient synthesis of aryl-substituted naphtho[2,1-a]azulenes by the combination of Suzuki–Miyaura,
Sonogashira, and cycloisomerization reactions is reported. The methodology
was applied to the synthesis of hitherto unknown azuleno[1,2-h]quinolines, cyclohepta[1,2]indeno[4,5-b]thiophenes, and cyclohepta[1,2]indeno[4,5-c]thiophenes.
The impact of different fused-heterocyclic rings on the photophysical
and electrochemical properties of these azulene derivatives was studied
by experimental and theoretical methods and hence provides a rationale
for the preparation of novel azulene derivatives with improved properties
for application as organic materials.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.