Fulgimides

Photochromic 1-benzofurylfulgides with modulated fluorescence

“…Its formation is caused by the substantial overlap of the absorption bands related to the S0→S1 transition of the initial ringopened form O and the S0→S2 transition of the photoinduced isomer C (Table 1). [12][13][14][15] The subsequent irradiation of colored solutions of 1a-c with visible light (λirr = 546 nm) leads to their photodecoloration due to the reverse ring-opening photoreaction C → E/Z-O (Fig. 1, curve 3).…”

“…The most thoroughly studied classes of organic photochromic compounds are represented by spiropyrans and spirooxazines, 8,9 azobenzenes, 10 dihetarylethenes, 11 fulgides and fulgimides. 12,13 Fulgides, the compounds with the structural skeleton of bismethylenesuccinic anhydride and an aromatic or heterocyclic substituent linked to a methylene group, are susceptible to the light-induced hexatriene-cyclohexadiene rearrangement of their ground state colourless ring-opened forms to give coloured ring-closed isomers possessing high fatigue resistance, thermal and photostability capable to display fluorescent, chemosensor and complexing properties. [14][15][16] These isomeric forms do not interconvert in dark and have markedly different physical chemical characteristics, which makes fulgides to be promising candidates for the use in high capacity three-dimensional multilayer optical memory devices.…”

Synthesis and highly efficient light-induced rearrangements of diphenylmethylene(2-benzo[b]thienyl)fulgides and fulgimides

“…Photochromic compounds are of considerable interest as molecular switches, elements of optical memory and molecular logic devices [1][2][3][4]. Fulgides and fulgimides possessing excellent thermal and photochemical stability, structurally modulated fluorescent properties and high quantum efficiencies of their light-induced pericyclic rearrangements constitute one of the most prospective and amply studied photochromic families [5][6][7][8][9][10][11][12]. A general approach to the synthesis of fulgides is based on a Stobbe condensation [13] of aromatic or heterocyclic aldehydes or ketones with methylene succinates followed by subse- quent hydrolysis and dehydration processes.…”

Synthesis, photo- and ionochromic properties of indolyl(thienyl)maleimides with phenanthroline receptor

“…Photochromic compounds that switch between isomeric states under irradiation with light of a certain wavelength are extensively studied. [1][2][3][4][5][6][7] Spirocyclic compounds, [8][9][10] fulgides and fulgimides, [11][12][13] dihetarylethenes, 14,15 photochromic heterocyclic ketoenamines 16,17 and norbornadienes 18,19 are of particular interest due to their potential industrial applications, including design of materials for molecular electronics, rewritable optical memory, photo optical commutation, organic displays, photo-pharmacology, biological data visualization, chemo-and biosensors. Chemical modification of photochromic molecules with ionochromic substituents opens new possibilities to create of photo controllable chemosensors in which the coordination and release of ions is modulated with light of different wavelengths.…”