The photophysical characterisation of novel 3,9-dialkyloxy- and diacyloxyperylenes

Abstract

The fundamental photophysical properties of three symmetrically substituted 3,9-perylene analogues were examined in a diverse range of solvents. All three compounds exhibited solvent-dependent fluorescence quantum yield, which was lower than that of perylene or its diimides. Whilst the absence of a large excited state dipole moment suggests that there is no preferential charge accumulation in one side of the molecules, the data suggest that intramolecular electron transfer occurs and that such an event causes additional photochemical mechanisms in chlorinated compounds where the fluorescence quantum yield is lower than in all other solvents and the values of the fluorescence decay change significantly. The dyes could be an interesting new class of fluorescence tags for labeling biomolecules and as dyes for organic photovoltaic materials.

Claisen rearrangement route to novel electron-rich perylene dyes

“…Product 5b exhibited the expected spectroscopic signals including UV/vis profile with the typical perylene absorbance pattern. 8 These findings establish a pathway for novel, electron-rich diallyldihydroxyperylene and its diester. 10 The products support potential sites for ligation or chemical modification en route to novel photoactive materials, which are under investigation in our laboratory and those of collaborators.…”

“…The former requires the preparation of acylated octahydroperylene intermediate 4b en route to 5b to avoid phenolic oxidation to quinones. 5,8 In the present work, we examined feasibility of both synthetic avenues to 5.…”

“…Novel product 5a and its ether (R = alkyl) derivatives are predicted to be easily elaborated to perylenes that are electronically activated toward photoemission. 8 Conversion from known 2d to 5b was planned via Claisen rearrangement followed by oxidation (Route A) or the reverse sequence (Route B). The former requires the preparation of acylated octahydroperylene intermediate 4b en route to 5b to avoid phenolic oxidation to quinones.…”

Combined Use of Optical Spectroscopy and Computational Methods to Study the Binding and the Photoinduced Conformational Modification of Proteins When NMR and X-Ray Structural Determinations Are Not an Option

“…are aromatic such as flavins, phenyls, carotenoids, etc. In our own experience, we have focused on two classes so far: porphyrins and perylenes (Fernandez et al, 2009;Fernandez et al, 2008;Fuini et al, 2011). A common characteristic of these ligands is that docking to proteins modifies their absorption and emission spectra.…”

Eaton’s Reagent‐Mediated Domino π‐Cationic Arylations of Aromatic Carboxylic Acids to Iasi‐Red Polymethoxylated Polycyclic Aromatic Hydrocarbons: Products with Unprecedented Biological Activities as Tubulin Polymerization Inhibitors

“…Certain examples of these products are used as dendritic polymers, [4] liquid-crystalline materials, [5] and electronic organic devices [6] including deep-blue organic light-emitting diodes (OLEDs), [7] fluorescent tags for labeling biomolecules, [8] and red-emitting electroluminescent materials. [9] On the other hand and in contrast to OH-PAHs, no examples of natural bioactive alkoxy-PAHs bearing one skeleton among PAHs family can be found in the literature.…”