Synthesis, metal ion binding, and photochromic properties of benzo- and naphthopyrans annelated by crown ether moieties

• Published in: Tetrahedron Vol. 68; no. 38; pp. 7873 - 7883
• Main Authors: Paramonov, Sergey V., Lokshin, Vladimir, Smolentsev, Artem B., Glebov, Evgeni M., Korolev, Valeri V., Basok, Stepan S., Lysenko, Konstantin A., Delbaere, Stéphanie, Fedorova, Olga A.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 23.09.2012; Elsevier
• Subjects: Baeyer–Villiger oxidation; Binding; Binding constants determination; Chemical Physics; Chemical Sciences; Chemistry; Chemistry, Organic; Chromenes; Complex formation; Construction; Crown ether; Crown ethers; Ethers; Host–guest complexes; Organic chemistry; Phenols; Photochromism; Physical Sciences; Physics; Science & Technology; Synthesis; Tetrahedrons; Chromenes; Host–guest complexes; Synthesis; Baeyer–Villiger oxidation; Photochromism; Crown ether; Binding constants determination; Baeyer-Villiger oxidation; BEHAVIOR; STABILITY-CONSTANTS; CHROMENE; Host-guest complexes; MEMORIES; ALPHA-CHYMOTRYPSIN; COMPLEXATION; DERIVATIVES
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2012.07.029

Combining a photochromic chromene with a crown ether moiety results in systems in which photochromism and ionophoric properties could significantly influence each other. In this paper, we report the synthesis of several chromenes annelated by 15(18)-crown-5(6) ethers. The approach involves the building of the photochromic fragment upon the initial crown ether via phenols. The two main routes for chromene preparation are discussed. The complex formation of the synthesized photochromic crown-containing naphthopyran with magnesium(II) and barium(II) cations was studied. The kinetic behavior of the colored form of the compound is affected by complex formation. [Display omitted]