Spectral properties and G-quadruplex DNA binding selectivities of a series of unsymmetrical perylene diimides

Polyaromatic Profluorescent Nitroxide Probes with Enhanced Photostability

“…We expected that the increased solubility of the initially formed monoimide over the dianhydride staringm aterial (21) would lead to the rapid formation of the symmetricald iimide, as described previously. Therefore, it wasreasoned that the desired nitroxide/N-octylaryl containing perylene diimides (23) could be accessed (after separation) in one-pot startingw ith am ixture of both aryl amines (Scheme6).…”

“…[9] As the solubility of nitroxide 2 was extremely poor in the majority of organic solvents, it was decided to focuso nt he preparation of unsymmetrical perylened iimides which would incorporate both anitroxide unit and asolubilisingg roup tethered through the covalent imide bonds onto the perylene unit similart ot he approach employed by Nagao. [20] Initial attempts to generate am ononitroxide-containingp erylene diimide involved the stepwise addition of 2,5-di-tert-butylanilinet o3 ,4,9,10-perylenetetracarboxylic dianhydride (21) in the presence of zinc acetate in molten imidazole at 130 8C as am eans to generate the monoanhydridew hich could subsequently be reactedw ith nitroxide 22.U nder these condi-Scheme3.Synthetic route to ethynyl-linkedn aphthalimide-based profluorescent nitroxide 14.…”

Fluorescent macromolecular perylene diimides containing pyrene or indole units in bay positions

“…The fluorescence decay times were taken on a sub-nanosecond pulsed LEDs. Details on the time-resolved measurements were reported elsewhere [22]. Optical density of the solutions which were used in the spectroscopic studies was below 0.1.…”

Synthesis of Alternative Electron Acceptor Compounds

“…The compounds were synthetized according to two methods settled on the basis of literature data [12][13][14][15][16][17]. Specifically, the new protocols proposed have allowed us to isolate the perylene monoimides easily and with good yields conversely to what we have obtained by following exclusively the literature synthetic pathways.…”