Synthesis, characterization and properties of shape-persistent macrocycles.
Phulwale B. V.
Department of Chemistry, Faculty of Science, Masaryk University, Kamenice 5, 625 00 BrnoBohunice,
Czech Republic.
Abstract
A conjugated, non-conjugated and donor-acceptor shape-persistent macrocycles have been made
up of from planar poly-aromatic building blocks, such as phenanthrenes and carbazoles, along with
acetylene, butadiynylene, thienylene, diethynylbenzene and bulky 1,3diethynylbicyclo[1.1.1]pentane
as linkers. Structure and properties of the macrocycles, such as
self-association in solution, optical and electrochemical properties were studied in a comparative
manner with respect to the effects of different size and shape of the macrocycles, and character
and length of their side chains. In a donor-acceptor macrocycles, an intermolecular charge-transfer
(ICT) interaction observed and was proven by observation of the solvatochromism. Further, the
effect of conjugated diethynylbenzene macrocycles and non-conjugated bulky 1,3diethynylbicyclo[1.1.1]pentane
on their properties were studied by various spectroscopic technics.
Phenanthrylene Macrocycles D-A Macrocycles
400 600 800
0.0
0.3
0.6
0.9
Abs(AU)
/ nm
CHCl3
DCM
THF
Toluene
Benzene
Dioxane
3a