Human serum albumin as vehicle for the solubilization of perylene diimides in aqueous solutions.

The chemical, physical and photophysical properties of perylene diimides have attracted substantial attention for the potential applications in diverse fields ranging from advanced materials to biomedical applications. Some applications require the diimides to be in aqueous environment where they tend to dissolve poorly. We investigated the use of human serum albumin as a vehicle to increase the aqueous exposure of monomeric perylene diimides.

Characterization of novel perylene diimides containing aromatic amino acid side chains.

Perylene diimide derivatives have attracted initial interest as industrial dyes. Recently, much attention has been focused on their strong π-π stacks resulting from the large PDI aromatic core. These PDI stacks have distinct optical properties, and provide informative models that could mimic light-harvesting systems and initial charge transfer typical of photosynthetic systems.

Simultaneous solid phase extraction and derivatization of aliphatic primary amines prior to separation and UV-absorbance detection.

To overcome the problem of poor sensitivity of capillary electrophoresis-UV absorbance for the detection of aliphatic amines, a solid phase extraction and derivatization scheme was developed. This work demonstrates successful coupling of amines to a chromophore immobilized on a solid phase and subsequent cleavage and analysis. Although the analysis of many types of amines is relevant for myriad applications, this paper focuses on the derivatization and separation of amines with environmental relevance.

Interaction of human serum albumin with novel 3,9-disubstituted perylenes.

Human serum albumin (HSA) has been used as a model for the binding of a number of different ligands, including polyaromatic hydrocarbons, to proteins. In this case we have investigated the interaction of HSA with a novel set of perylene derivatives. Di-substituted perylene analogues have been synthesized as potentially useful organic photovoltaic materials.

The photophysical Characterisation of Novel 3,9-Dialkyloxy- and Diacyloxyperylenes.

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.

4,10-Diall-yloxy-1,2,3,6b,7,8,9,12b-octa-hydro-perylene.

In the title compound, C(26)H(28)O(2), the central atoms are coplanar, with the -CH(2)-CH(2)- links of the cyclo-hexene groups lying to either side of the plane and with the diall-yloxy residues twisted out of this plane [C-C-O-C torsion angles = 16.6 (3) and -13.9 (3)°].

Tandem Friedel-Crafts annulation to novel perylene analogues.

Novel dialkyloxy- and dihydroxyoctahydroperylenes are regioselectively available via a new tandem Friedel-Crafts alkylation of tetrahydronaphthalene precursors followed by oxidative aromatization. Heating of 5-alkyloxy-1-tetralol with p-toluenesulfonic acid in sulfolane gave the corresponding octahydroperylenes in moderate yields. Studies with Lewis acids and tetralin-1,5-diol in acetonitrile at room temperature provided the 4,10-dihydroxy analogue cleanly, albeit in reduced yields.