Abstract
Heptalene has a fused structure of two cycloheptatrienes which is one of the non-aromatic bicyclic molecules with a 12π-electronic structure. We report herein the synthesis of thiophene-fused heptalene derivatives from the corresponding azulenothiophenes via cycloaddition reaction with dimethyl acetylenedicarboxylate. Their structure was clarified by single-crystal X-ray structural analysis. The electronic properties of the thiophene-fused heptalenes obtained by this study were characterized by UV/Vis and fluorescence spectroscopy measurements. The electrochemical features of these derivatives were also examined by voltammetry and spectroelectrochemical experiments.
Highlights
Heptalene has a fused structure of two cycloheptatrienes which is one of the non-aromatic bicyclic molecules with a 12π-electronic structure
In addition to the above synthetic procedures, preparation of the heptalene skeleton is established by using the reaction of azulene derivatives with dimethyl acetylenedicarboxylate (DMAD)
There are few examples of the synthesis of heptalenes by the reaction of ring-fused azulene derivatives with DMAD, and the properties of the ring-fused heptalene derivatives have hardly been evaluated, a number of azulene derivatives may become a promising precursor for the heptalene synthesis
Summary
Heptalene has a fused structure of two cycloheptatrienes which is one of the non-aromatic bicyclic molecules with a 12π-electronic structure. The reaction of benzo[a]azulene with DMAD gives benzene-fused heptalene derivative 2b, which is demonstrated by Yasunami et al.[5]. We have reported the synthesis, optical and electrochemical properties of azulenothiophene derivatives[23,26,27,28] that become good precursors for the thiophene-fused
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
