Synthesis of thiophene-fused heptalenes by cycloaddition of azulenothiophenes with dimethyl acetylenedicarboxylate

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.

Gold(I)‐Catalyzed Intramolecular 7‐endo‐dig Cyclization of Triene‐Yne Systems: New Access towards Azulenothiophenes

“…A potential use of our target molecules for further investigations and utilizations as organic materials seems reasonable and UV/Vis spectra and cyclic voltammograms were already recorded. Further studies might also address the potential transformation of the obtained azulenothiophenes towards heptalene derivatives, [31] which would also have impact for the field of organic materials.…”

Gold(I)‐katalysierte Intramolekulare 7‐endo‐dig Zyklisierung von Trien‐In‐Systemen: Neuer Zugang zu Azulenothiophenen

“…Weitere elektronische Untersuchungen unserer Zielmoleküle für die Nutzungen als organische Materialien erscheint sinnvoll, wobei UV/Vis-Spektren und Cyclovoltammogramme bereits aufgenommen wurden. Weitere Studien könnten sich auch mit der möglichen Umwandlung der erhaltenen Azulenothiophene in Heptalenderivate befassen, [31] was auch Auswirkungen auf den Bereich organischer Materialien hätte.…”