Synthesis, Structural, and Optical Properties of Azuleno[1,2-<i>c</i>]pyran-1-ones: Bronsted Acid-Mediated Cyclization of 2-Azulenylalkynes
Taku Shoji, Nichika Sasahara, Atom Hamasaki, Shigeki Mori, Tetsuo Okujima, Ryuta Sekiguchi, Shunji Ito
Abstract
Pyrones and their aromatic ring-fused derivatives have gained significant attention due to their diverse biological activities and potential as foundational frameworks for advanced materials. In this paper, we describe a proficient approach for the preparation of azuleno[1,2- c ]pyran-1-ones, which are difficult to produce by using conventional methods. The synthesis was achieved through Bro̷nsted acid-mediated cyclization of 2-azulenylalkynes. The structural and optical properties of azuleno[1,2- c ]pyran-1-ones were characterized by single-crystal X-ray analysis, NMR, UV/vis, and fluorescence spectroscopies. Under acidic conditions, these compounds displayed notable spectral alterations and emission, distinct from their spectra in neutral medium. These results suggest that azuleno[1,2- c ]pyran-1-ones hold great potential for applications in organic electronic materials and fluorescent pH sensors.