Photoinitiated Rearrangements of 3-Phenylnorbornadiene with conjugated Substituents in 2-Position

Norbornadiene–quadricyclane as an abiotic system for the storage of solar energy

“…We have studied the spectral and photochemical features of 3-phenylnorbornadiene-2-carboxamides 24. 66,67 Compounds 24 are characterised by absorption in the region 280 ± 305 nm (Table 3) and l ae = 375 ± 435 nm. 66,67 Irradiation with light with a wavelength corresponding to the long-wave absorption maximum (l irr = 313 nm) results in their isomerisation to give quadricyclanes 25 with high quantum yields.…”

“…66,67 Compounds 24 are characterised by absorption in the region 280 ± 305 nm (Table 3) and l ae = 375 ± 435 nm. 66,67 Irradiation with light with a wavelength corresponding to the long-wave absorption maximum (l irr = 313 nm) results in their isomerisation to give quadricyclanes 25 with high quantum yields. Electron-withdrawing substituents in the N-phenyl ring increase the F value in comparison with non-substituted 3-phenyl-2-(N-phenylcarbamoyl)norbornadiene 24a, whereas electron-donor substituents decrease this Since the triplet mechanism of isomerisation of norbornadiene into quadricyclane can occur with high quantum yields in the presence of aromatic ketones, we studied norbornadienes 26 with one of the C=C bonds involved in the conjugation chain of the Ph7C=C7C=X fragment (Table 4).…”

“…(Table 5). 67,69,71,72 By varying the electron-donating and electron-withdrawing substituents at the C=C double bond in norbornadienes 28, it became possible to shift the values of l max to 500 nm and l ae to 620 nm. Heterogeneous catalysis with Mo(VI) oxide described above proved to be efficient for the reverse reaction of the majority of quadricyclanes 29.…”

“…We have studied the photochemical properties of 2-benzooxazolyl and 2-benzoimidazolyl derivatives of 3-phenylnorbornadiene 33a,b. 67,69,80 The benzooxazole derivative 33a is characterised by l ae = 550 nm, but the 33a ? 34a rearrangement occurs irreversibly.…”

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.…”