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PubMed2000

Hierarchical self-organization of perylene bisimide--melamine assemblies to fluorescent mesoscopic superstructures.

A series of three perylene tetracarboxylic acid bisimide dyes 3a-c bearing phenoxy substituents at the four bay positions of the perylene core were synthesized and their complexation behavior to complementary ditopic dialkyl melamines 8a-c was investigated. Binding constants and Gibbs binding energies for the hydrogen bonds between the imide and the complementary melamine moiety have been determined in several solvents by NMR and UV/Vis titration experiments with monotopic model compounds 5 and 9. The effects of the solvent polarity and specific solvent-solute interactions on the degree of polymerization of (3 x 8)n are discussed, and a general formula to estimate the chain length of [AA-BB]n nylon-type supramolecular polymers is derived. In addition to the formation of a hydrogen-bonded supramolecular chain. pi-pi interactions were observed for perylene bisimide-melamine assemblies 3b x 8b and 3b x 8c in aliphatic solvents. The orthogonal nature of hydrogen bonding and pi-pi interactions leads to three-dimensional growth yielding large-sized aggregates already in dilute solution. On suitable substrates, densely intertwined networks of nano- to mesoscopic strands are formed which have been investigated by electron microscopy, confocal fluorescence microscopy and optical polarization microscopy. The high fluorescence and excellent photostability of these superstructures is promising for future studies on energy migration and artificial light harvesting at the nano- and mesoscopic length scale.

Chlorophyll↗
PubMed2004

Towards highly fluorescent and water-soluble perylene dyes.

A systematic approach towards highly fluorescent, water-soluble perylene-3,4:9,10-tetracarboxylic acid diimide chromophores is presented. Water solubility was introduced first through the attachment of four hydrophilic substituents onto the bay region of the perylene dye. Positively and negatively charged groups were then applied to the chromophore, and their number and their distance from the aromatic scaffold were systematically varied. To suppress aggregation, the chromophore was further isolated within a dendritic shell. Such variation of structural features and a thorough investigation of the resulting optical properties facilitated the first synthesis of perylene-3,4:9,10-tetracarboxylic acid diimides combining the properties of water solubility and fluorescence quantum yields (FQYs) close to unity, which makes them attractive as high-performance fluorescence probes in aqueous media.

Fluorescent Dyes↗
PubMed1983

Dinitro and mononitrobenzo(ghi)perylenes and mononitrocoronene are highly mutagenic in the Ames Salmonella assay.

Benzo(ghi)perylene (B(ghi))Per, (191-24-2)) and coronene (Cor, (191-07-1)) are major constituents of the polycyclic aromatic hydrocarbons (PAH) found in automobile exhaust and polluted air [eg, Grimmer et al, 1981]. Nitration of these PAH by NO2 and traces of HNO3, which are also formed in automobile exhaust, seems highly probable. To identify the presence of these nitroarenes in environmental samples and to examine their mutagenic potencies we synthesized and characterized nitro derivatives of both PAH. 5-NO2B(ghi)Per (81316-87-2) and 1-NO2Cor (81316-84-9) produced 405 and 340 revertants/nmole respectively in TA98 in the presence of 0.6 mg of microsomal enzymes (S-9) per plate in the Ames test. 5,8-diNO2B(ghi)Per (83292-25-5) and 5,10-diNO2B(ghi)Per (83292-26-6) produced 21,500 and 4,000 revertants/nmole in TA98 without microsomal activation. Mutagenicity for the dinitrobenzo(ghi)perylenes was also high in TA98NR and TA97 but was reduced by 97% in TA98-1,8DNP. There is close similarity in the orientation and distances between reactive sites (nitrenium ion and carbocation) on the dinitrobenzo(ghi)perylenes and 1,6-dinitropyrene (42397-64-8) and 1,8-dinitropyrene (42397-65-9).

Animals↗
PubMed2000

Studies of archaebacterial bipolar tetraether liposomes by perylene fluorescence.

Membrane packing and dynamics of bipolar tetraether liposomes composed of the polar lipid fraction E (PLFE) from the thermoacidophilic archaebacterium Sulfolobus acidocaldarius have been studied by perylene fluorescence. At a probe-to-PLFE lipid ratio of 1:400, we have detected an unusual fluorescence intensity increase with increasing temperature, while the fluorescence lifetime changed little. As the ratio was decreased, the intensity anomaly was diminished. At 1:3200 and 1:6400, the anomaly disappeared. A remarkable perylene intensity anomaly was also observed in bilayers composed of saturated monopolar diester phosphatidylcholines at their main phase transition temperatures. These results suggest that the intensity anomaly may be due to probe aggregation caused by tight membrane packing. At the same probe-to-lipid ratio (1:400), however, 1, 2-diphytanoyl-sn-glycero-3-phosphocholine (DPhPC) and 1, 2-diphytanoyl-sn-glycero-3-phosphoglycerol (DPhPG) liposomes did not exhibit any intensity anomaly with increasing temperature. This suggests that DPhPC and DPhPG liposomes are more loosely packed than PLFE liposomes; thus the branched methyl groups are not the contributing factor of the tight membrane packing found in PLFE liposomes. Using a multiexcitation method, we have also determined the average (R), in-plane (R(ip)), and out-of-plane (R(op)) rotational rates of perylene in PLFE liposomes at various temperatures (20-65 degrees C). R and R(ip), determined at two different probe-to-lipid ratios (1:400 and 1:3200), both undergo an abrupt increase when the temperature is elevated to approximately 48 degrees C. These data suggest that PLFE liposomes are rigid and tightly packed at low temperatures, but they begin to possess appreciable "membrane fluidity" at temperatures close to the minimum growth temperature ( approximately 50 degrees C) of thermoacidophilic archaebacteria.

Ethers↗
PubMed2002

Perylene diimide G-quadruplex DNA binding selectivity is mediated by ligand aggregation.

Two N,N'-disubstituted perylene diimide G-quadruplex DNA ligands, PIPER [N,N'-bis-(2-(1-piperidino)ethyl)-3,4,9,10-perylene tetracarboxylic acid diimide] and Tel01 [N,N'-bis-(3-(4-morpholino)-propyl)-3,4,9,10-perylene tetracarboxylic acid diimide] were studied. Visible absorbance, resonance light scattering, and fluorescence spectroscopy were used to characterize the pH-dependent aggregation of these ligands. The G-quadruplex DNA binding selectivity of these ligands as monitored by absorption spectroscopy is also pH-dependent. The ligands bind to both duplex and G-quadruplex DNA under low pH conditions, where the ligands are not aggregated. At higher pH, where the ligands are extensively aggregated, the apparent G-quadruplex DNA binding selectivity is high.

Anthracenes↗
PubMed2006

Perylene-3,4:9,10-tetracarboxylic acid bisimide dye as an artificial DNA base surrogate.

A phosphoramidite of the perylene bisimide dye was synthesized as a DNA building block that allows incorporation of this chromophore as an artificial nucleoside surrogate either at the 5'-terminus or at internal positions of duplex DNA. The internally incorporated perylene bisimide chromophore shows strong interactions with the DNA base stack; the 5'-terminally attached perylene bisimide is able to induce dimerization of two whole DNA duplexes.

Base Sequence↗
PubMed1984

[Structural changes in the myelin sheath membranes detectable by using the nonpolar probe perylene. A fluorescence polarization study].

Perylene as a fluorescent probe has been used to investigate membranes of the myelin sheath of surviving nerve fibres. Fluorescence polarization (P) of perylene was measured in stained nerve fibres, and their dependence on the angle (AD) between the geometrical axis of the fibre and electrical vector of exciting light was studied. The dependence of AD on the temperature showed that P (90 degrees) decreased gradually when the temperature increased at heating within the range of 0-32 degrees. A model of the prove movement in the lipid matrix is described. This model considers the rotation around the axis perpendicular to the plane of the perylene molecule only. Comparison of the results of model calculations and the experimental data allows to estimate the value of energy of viscosity activation. It proved to be 20-25 kcal/mol. Possible causes of such a high value of the kinetic barrier are discussed.

Animals↗
PubMed2001

Novel perylene chromophores obtained by a facile oxidative cyclodehydrogenation route.

New perylene chromophores, phenyl-substituted diindeno[1,2,3-cd:1',2',3'-lm]perylenes 5a,b and 4,4',7,7'-tetraphenyldiacenaphtho[1,2-k:1',2',k']diindeno[1,2,3-cd:1',2',3'-me]perylenes 22a,b, have been synthesized from substituted fluoranthene derivatives 3a,b and 4a,b by means of a surprisingly simple oxidative cyclodehydrogenation reaction. The resulting chromophores, when substituted with alkyl chains at the periphery, show good solubility in organic solvents, and a full characterization of the novel red, green, and blue dyes by field-desorption mass spectrometry, UV/Vis and 1H and 13C NMR spectroscopy becomes possible.

Journal Article↗
PubMed2007

Fluorescent perylene diimide rotaxanes: spectroscopic signatures of wheel-chromophore interactions.

[2]- and [3]-rotaxanes with a tetraphenoxy perylene diimide core were synthesized. Hydrogen bonding between the wheel and the imide changes the optical properties of the perylene chromophore: the absorption and fluorescence spectra are red-shifted. The decay times of the rotaxanes are shorter in comparison with that of the axle. Single molecule fluorescence measurements reveal relatively narrow distributions of emission maxima and decay times. The averages are in agreement with ensemble measurements. The observed red shifts make the perylene diimide a suitable chromophore for sensing the position of the wheel on the axle.

Journal Article↗
PubMed2007

Liquid-crystalline and electron-deficient coronene oligocarboxylic esters and imides by twofold benzogenic Diels-Alder reactions on perylenes.

Alkyl esters, imides and imido-esters of coronene-tri-, -tetra- and -octacarboxylic acids are accessible by a twofold oxidative benzogenic Diels-Alder reaction. Alkyl acrylates add to perylene, and maleic alkyl imides react twice with perylene as well as with perylene-tetracarboxylic tetraesters. Coronenes substituted with a greatly variable number of electron-withdrawing substituents are thus accessible, and di- and tetraimide derivatives are shown to be very pronounced electron-acceptor materials. The tri- and tetraalkyl esters and imidoesters self-assemble into columnar liquid-crystalline phases.

Journal Article↗
PubMed2003

Self-assembly of ferrocene-functionalized perylene bisimide bridging ligands with PtII corner to electrochemically active molecular squares.

Ferrocenyl-substituted N,N'-di(4-pyridyl)perylene bisimide ligands have been synthesized by the coupling reaction of hydroxyphenoxy-perylene bisimides with ferrocenyl carboxylic acids. By means of metallosupramolecular self-assembly, hitherto unprecedented multiredox active dendritic molecular squares with 16 ferrocene groups positioned in the bridging ligands are prepared from the perylene bispyridyl imide ligands and [Pt(dppp)][(OTf)(2)] (dppp = 1,3-bis(diphenylphosphano)propane; OTf = trifluoromethanesulfonate) corner in high yield. The isolated metallosupramolecular squares were characterized by elemental analysis, (1)H, (31)P[(1)H] NMR, and UV/vis spectroscopy. The electrochemical properties of the ligands and squares are investigated by cyclic voltammetry as well as spectroelectrochemistry. The results obtained show that the redox behavior of ferrocene units is influenced by the square superstructure. Furthermore, redox titration of free ligand and corresponding molecular square with the one-electron oxidant thianthrenium pentachloroantimonate reveals that ferrocene groups in these structures may be oxidized completely by this oxidant, and highly charged species generated through oxidation of ferrocenyl groups in molecular square cause decomposition of the assembly due to pronounced Coulombic repulsion.

Journal Article↗
PubMed2006

Twisted, Z-shaped perylene bisimide.

The first derivative of a new class of perylene bisimide chromophores, N,N'-bis(octyl)-3,9-bis(phenyl)perylene-1,2,7,8-tetracarboxyl bisimide, 1, has been synthesized and its fundamental photophysical and electrochemical properties assessed. The extended, Z-shaped structure was achieved by use of the classic photoenolization of an o-methylbenzophenone analogue, 1,5-dibenzoyl-9,10-dihydroanthracene, and in situ Diels-Alder trapping of the resulting o-xylylenol intermediates with N-octylmaleimide. Subsequent dehydration and aromatization of the resulting bisadduct afforded 1. In dichloromethane, bisimide 1 has an absorption lambdamax at 491 nm (epsilon = 29,600 M-1 cm-1), a fluorescence lambdamax at 517 nm with a high quantum yield (Phi = 0.70), and a single-exponential fluorescence decay (tau = 5.01 ns). Pure crystals of 1 have red emission, suggesting exciplex formation in the solid state. X-ray crystallographic analysis of 1 revealed significant twisting of its perylene core.

Journal Article↗
PubMed2006

Effect of side-chain substituents on self-assembly of perylene diimide molecules: morphology control.

Effect of side-chain substitutions on the morphology of self-assembly of perylene diimide molecules has been studied with two derivatives modified with distinctly different side-chains, N,N'-di(dodecyl)-perylene-3,4,9,10-tetracarboxylic diimide (DD-PTCDI) and N,N'-di(nonyldecyl)-perylene-3,4,9,10-tetracarboxylic diimide (ND-PTCDI). Due to the different side-chain interference, the self-assembly of the two molecules results in totally different morphologies in aggregate: one-dimensional (1D) nanobelt vs zero-dimensional (0D) nanoparticle. The size, shape, and topography of the self-assemblies were extensively characterized by a variety of microscopies including SEM, TEM, AFM, and fluorescence microscopy. The distinct morphologies of self-assembly have been obtained from both the solution-based processing and surface-supported solvent-vapor annealing. The nanobelts of DD-PTCDI fabricated in solution can feasibly be transferred to both polar (e.g., glass) and nonpolar (e.g., carbon) surfaces, implying the high stability of the molecular assembly (due to the strong pi-pi stacking). The side-chain-dependent molecular interaction was comparatively investigated using various spectrometries including UV-vis absorption, fluorescence, X-ray diffraction, and differential scanning calorimetry. Compared to the emission of ND-PTCDI aggregate, the emission of DD-PTCDI aggregate was significantly red-shifted (ca. 30 nm) and the emission quantum yield decreased about three times, primarily due to the more favorable molecular stacking for DD-PTCID. Moreover, the aggregate of DD-PTCDI shows a pronounced absorption band at the longer wavelength, whereas the absorption of ND-PTCDI aggregate is not significant in the same wavelength region. These optical spectral observations are reminiscent of the previous theoretical investigation on the side-chain-modulated electronic properties of PTCDI assembly.

Journal Article↗
PubMed2006

Bis(n-octylamino)perylene-3,4:9,10-bis(dicarboximide)s and their radical cations: synthesis, electrochemistry, and ENDOR spectroscopy.

1,6- and 1,7-bis(n-octylamino)perylene-3,4:9,10-bis(dicarboximide) were synthesized by reaction of n-octylamine with the corresponding dibromo compounds. These compounds display intense charge-transfer optical transitions in the visible spectrum (approximately 550-750 nm) and fluoresce weakly (Phi(F) < 0.06). Cyclic voltammetry reveals that each chromophore undergoes facile and reversible oxidation and reduction. Spectroelectrochemical studies show that the radical cations of these chromophores are stable and show no signs of deprotonation of the secondary amines. Electron paramagnetic resonance (EPR) and electron-nuclear double resonance (ENDOR) studies of the chemically generated radical cations of these chromophores corroborate the spectroelectrochemical data by showing that the radical cations persist for days at room temperature in methylene chloride solution. These experiments and complementary density functional theory (DFT) calculations provide a comprehensive picture of the molecular orbitals, spin density distributions, and geometries of the radical cations. The redox properties and stability of these alkylamino-functionalized perylene compounds make them a valuable addition to the family of robust perylene-based chromophores that can be used to develop new photoactive charge transport materials.

Journal Article↗
PubMed2005

Single molecule study of perylene orange photobleaching in thin sol-gel films.

The paper reports on photobleaching mechanisms of perylene orange embedded in thin sol-gel films, derived from single molecule studies. The experimental configuration uses wide-field illumination and one photon excitation of the molecules. Measurements have been performed both at ambient conditions and under vacuum in order to get information on the influence of oxygen on photobleaching in such porous samples. We have also recorded the evolution of photobleaching with respect to the excitation intensity. The results demonstrate that photobleaching from excited states higher than the first singlet and triplet states has a nonnegligible contribution as soon as the excitation energy exceeds a few hundred W/cm2 and that this process is favored in the presence of air. The study also demonstrates that perylene orange in sol-gel films is not a very efficient emitter but that photobleaching can be slow, which explains the interest for perylene orange as a good candidate to produce long lifetime solid-state lasers when embedded in monoliths of sol-gel.

Journal Article↗
PubMed2005

Oxidative transformations of surface-bound perylene.

We report on the covalent attachment of perylene derivatives to silica and indium-doped tin oxide surfaces. The spectroscopic properties of the immobilized fluorophores are studied by steady-state and time-resolved emission spectroscopy. The redox properties of the molecules are examined by electrochemical methods. It was found that the oxidation of perylene in aqueous medium results in the formation of perylenequinones. The transformation proceeds through a number of steps, with monohydroxyperylene(s) being the intermediate species. The final oxidation products are three isomeric forms of the perylenequinone/perylenehydroquinone redox couple. Understanding the mechanism of perylene transformation allows estimation of the concentration of molecules on the surface, and comparison of these results to those for pyrene and anthracene derivatives underscores the generality of this type of oxidative degradation for polycyclic aromatic hydrocarbons.

Journal Article↗
PubMed2006

Photodegradation of polymer-dispersed perylene di-imide dyes.

Polymer-dispersed perylene di-imide dye photodegradation is investigated by monitoring the fluorescence intensity as a function of 532 nm laser pulses. Anaerobically irradiated polymer-dye films exhibited an accelerated decrease in fluorescence intensity, which was partially recovered upon exposure to oxygen. Decelerated photodegradation rates were observed for perylene di-imide ethanol solutions upon the addition of a singlet oxygen quenching antioxidant. These observations suggest reversible photoreduction and type II photo-oxidation as important photodegradation mechanisms. Type II photo-oxidation for perylene red 532 nm irradiation is supported by a singlet oxygen quantum yield of 0.09+/-0.03, determined via detection of time-resolved O2 (a1delta(g) --> X3sigma(g)-) infrared phosphorescence.

Journal Article↗
PubMed2006

Fluorescent image analysis of lipid hydroperoxides in fish muscle with 3-perylene diphenylphosphine.

A fluorescent image analysis method was developed to evaluate lipid hydroperoxide formation in fish muscle. The lipid hydroperoxides generated in white and dark fish muscles during storage at 5-6 degrees C oxidized 3-perylene diphenylphosphine located in the tissue to yield the fluorescent derivative, 3-perylene diphenylphosphine oxide (3-PeDPPO). 3-PeDPPO thus obtained was determined by digital fluorescent image analysis. The 3-PeDPPO fluorescence intensity of white and dark muscle increased during low-temperature storage (0-24 h) and was clearly correlated with total lipid hydroperoxide levels in muscle extracts, which were determined by using HPLC based on a triphenylphosphine oxidation method (R2 = 0.954). These results suggest that 3-PeDPPO fluorescence, coupled with fluorescent image analysis, is a novel tool for direct determination of lipid hydroperoxides in fish muscle without a need for extraction of lipid.

Animals↗