Premium
Synthesis and characterization of new derivatives of azulene, including experimental and theoretical studies of electronic and spectroscopic behavior
Author(s) -
Förster Sebastian,
Hahn Torsten,
Loose Claudia,
Röder Christian,
Liebing Simon,
Seichter Wilhelm,
Eißmann Frank,
Kortus Jens,
Weber Edwin
Publication year - 2012
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.2934
Subject(s) - azulene , chemistry , cyclic voltammetry , density functional theory , computational chemistry , conjugated system , raman spectroscopy , combinatorial chemistry , photochemistry , organic chemistry , electrochemistry , polymer , physics , electrode , optics
Four new azulene derivatives featuring two π‐conjugated and sulfur terminated rigid side arms in the 1,3‐positions of the azulene core were designed, synthesized, and characterized. The syntheses were carried out on the basis of a palladium cross‐coupling procedure in the key reaction step. The crystal structures of the target compound 3 and of the intermediate compounds 7 and 9 have been studied. Supporting density functional theory calculations reveal insights into the electronic properties of the particular azulenes. The comparison of measured UV–Vis, infrared, and Raman data to calculated values allowed assignment of major spectral features to the particular structural differences of the new compounds and comparison to plain azulene. Cyclic voltammetry measurements were performed showing the redox characteristics of the new azulene derivatives. Copyright © 2012 John Wiley & Sons, Ltd.