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Two-photon absorption of perylene derivatives: Interpreting the spectral structure

PIOVESAN, E.; SILVA, D. L.; BONI, L. De; GUIMARAES, Francisco Eduardo Gontijo; MISOGUTI, Lino; ZALESNY, R.; BARTKOWIAK, W.; MENDONCA, Cleber Renato
Fonte: ELSEVIER SCIENCE BV Publicador: ELSEVIER SCIENCE BV
Tipo: Artigo de Revista Científica
ENG
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This work investigates the two-photon absorption spectrum of perylene tetracarboxylic derivatives using the white-light continuum Z-scan technique. Perylene derivatives present relatively high two-photon absorption cross-section, which makes them attractive for applications in photonics. Because of the spectral resolution of the white-light continuum Z-scan, we were able to observe a well defined structure in the two-photon absorption spectrum, composed by two distinct peaks. These peaks, as well as the resonant enhancement of the nonlinearity, were modeled using the sum-over-states approach considering a four-level energy diagram with two final two-photon states. The existence of such states was confirmed using the response function formalism within the DFT framework. (C) 2009 Elsevier B.V. All rights reserved.; FAPESP (Funda ao de Amaparo a Pesquisa do Estado de Sao Paulo); Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP); Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq); CNPq (conselho Nacional de Desenvolvimento Cientifico e Tecnoloogico); U.S. Air Force Office of Scientific Research (AFOSR); Air Force Office of Scientific Research (AFOSR) [FA9550-07-1-0374]; European Commission; European Commission[MRTN-CT-2006-035859]

Ultrafast dynamics of bis (n-butylimido) perylene thin films excited by two-photon absorption

MENDONCA, C. R.; KANDYLA, M.; SHIH, T.; AROCA, R. F.; CONSTANTINO, C. J. L.; MAZUR, E.
Fonte: SPRINGER Publicador: SPRINGER
Tipo: Artigo de Revista Científica
ENG
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We report a pump-probe study of the two-photon induced reflectivity changes in bis (n-butylimido) perylene thin films. To enhance the two-photon excitation we deposited bis (n-butylimido) perylene films on top of gold nanoislands. The observed transient response in the reflectivity spectrum of bis (n-butylimido) perylene is due to a depletion of the molecule`s ground state and excited state absorption.; National Science Foundation (NSF)[DMI- 0334984]; U.S. National Science Foundation (NSF); Army Research Office; Army Research Office[W911NF-05-1-0471]; U.S. National Science Foundation (NSF); NSF Graduate Research Fellowship; FAPESP and CAPES ( Brazil); Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP); Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)

Investigation of the two-photon absorption cross-section in perylene tetracarboxylic derivatives: Nonlinear spectra and molecular structure

Correa, D. S.; Oliveira, S. L.; Misoguti, L.; Zilio, S. C.; Aroca, R. F.; Constantino, CJL; Mendonca, C. R.
Fonte: Amer Chemical Soc Publicador: Amer Chemical Soc
Tipo: Artigo de Revista Científica Formato: 6433-6438
ENG
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We investigated the 2PA absorption spectrum of a family of perylene tetracarboxylic derivatives ( PTCDs): bis( benzimidazo) perylene ( AzoPTCD), bis( benzimidazo) thioperylene ( Monothio BZP), n-pentylimidobenzimidazoperylene ( PazoPTCD), and bis( n-butylimido) perylene ( BuPTCD). These compounds present extremely high two-photon absorption, which makes them attractive for applications in photonics devices. The two-photon absorption cross-section spectra of perylene derivatives obtained via Z-scan technique were fitted by means of a sum-over-states ( SOS) model, which described with accuracy the different regions of the 2PA cross-section spectra. Frontier molecular orbital calculations show that all molecules present similar features, indicating that nonlinear optical properties in PTCDs are mainly determined by the central portion of the molecule, with minimal effect from the lateral side groups. In general, our results pointed out that the differences in the 2PA cross-sections among the compounds are mainly due to the nonlinearity resonance enhancement.

Two-photon absorption in perylene derivatives

De Boni, L.; Constantino, CJL; Misoguti, L.; Aroca, R. F.; Zilio, S. C.; Mendonca, C. R.
Fonte: Elsevier B.V. Publicador: Elsevier B.V.
Tipo: Artigo de Revista Científica Formato: 744-749
ENG
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This work reports on the two-photon absorption (2PA) cross-section for bis (n-butylimido) perylene (BuPTCD), bis (benzimidazo) perylene (AzoPTCD), bis (benzimidazo) thioperylene (Monothio BZP), bis (phenethylimido) perylene (PhPTCD), bis (benzylimido) perylene (BePTCD) and n-pentylimido-benzimidazo perylene (PAzoPTCD) solutions measured using the Z-scan technique with femtosecond laser pulses at 775 nm. All perylene derivatives studied present large 2PA cross-sections, only comparable to the best ones reported in the literature. The experimental 2PA cross-sections obtained for each PTCD compound are in good agreement with a simplified sum-over-state calculation. The results of the present work indicates perylene derivatives as promising materials for two-photon applications. (C) 2003 Elsevier B.V. B.V. All rights reserved.

Nanostructured films of perylene derivatives: High performance materials for taste sensor applications

Constantino, C. J L; Antunes, P. A.; Venancio, E. C.; Consolin, N.; Fonseca, F. J.; Mattoso, L. H C; Aroca, R. F.; Oliveira, O. N.; Riul, A.
Fonte: Universidade Estadual Paulista Publicador: Universidade Estadual Paulista
Tipo: Artigo de Revista Científica Formato: 95-101
ENG
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Four perylene derivatives (PTCD) have been used as transducing materials in taste sensors fabricated with nanostructured Langmuir-Blodgett (LB) films deposited onto interdigitated gold electrodes. The Langmuir monolayers of PTCDs display considerable collapse pressures, with areas per molecule indicative of an edge-on or head-on arrangement for the molecules at the air/water interface. The sensing units for the electronic tongue were produced from 5-layer LB films of the four PTCDs, whose electrical response was characterized with impedance spectroscopy. The distinct responses of the PTCDs, attributed to differences in their molecular structures, allowed one to obtain a finger printing system that was able to distinguish tastes (salty, sweet, bitter and sour) at 1 μM concentrations, which, in some cases, are three orders of magnitude below the human threshold. Using Principal Component Analysis (PCA) data analysis, the electronic tongue also detected trace amounts of a pesticide and could distinguish among samples of ultrapure, distilled and tap water, and two brands of mineral water. © 2004 by American Scientific Publishers. All rights reserved.

Nonlinear absorption spectrum in perylene derivatives

Oliveira, S. L.; De Boni, L.; Corrêa, D. S.; Misoguti, L.; Zílio, S. C.; Mendonça, C. R.; Constantino, C. J L; Aroca, R. F.
Fonte: Universidade Estadual Paulista Publicador: Universidade Estadual Paulista
Tipo: Conferência ou Objeto de Conferência Formato: 1277-1279
ENG
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Knowledge about nonlinear absorption spectra of materials used in photonic devices is of paramount importance in determining their optimum operation wavelengths. In this work, we have investigated the two-photon absorption (2PA) degenerate cross-section spectrum for perylene derivatives using the Z-scan technique with femtosecond laser pulses. All perylene derivatives studied present large 2PA cross-sections, only comparable to the best ones reported in the literature. The results achieved in the present investigation indicate perylene derivatives as promising materials for two-photon applications. ©2005 Optical Society of America.

Perylene toxicity in the estuarine environment of Ria de Aveiro (Portugal)

Cunha, A.; Almeida, A.; Ré, A.; Martins, A.; Alcantara, F.
Fonte: Springer Verlag Publicador: Springer Verlag
Tipo: Artigo de Revista Científica
ENG
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Perylene, a 5-ring polycyclic aromatic hydrocarbon is common in estuarine sediments and its toxicity in the benthic and planktonic compartments is not yet clarified. The objectives of this work were: (1) to follow the toxicity of high concentrations of perylene (110 mg l−1) on benthic bacteria and macrofauna (amphipod Corophium multisetosum); (2) to determine the effects of a low load of perylene (2 μg l−1) on the metabolism of suspended bacteriobenthos after 9-day exposure, mimicking the effects of tidal erosion; (3) to contrast the effects of this low perylene load on the particle-free bacterioplankton and on the suspended and particle-adhered bacteriobenthos. No impact was detected in bacterial abundance exposed to 110 mg perylene l−1 for 9 days. This concentration of perylene evoked no acute effects in C. multisetosum but, chronic toxicity assays revealed statistically significant negative effects on survival, growth and number of pregnant females. The bacterioplankton and the suspended bacteriobenthos, exposed to 2 μg perylene l−1 during 2 weeks, responded with altered profiles of activity when compared to the control suspension. These values ranged, respectively, for bacterial biomass production from 134 to 210 and from 24 to 184 μg C l−1 h−1...

Synthesis, photophysical and electrochemical properties of perylene dyes

Torres, Erica; Berberan-Santos, M. N.; Brites, Maria João
Fonte: Elsevier Publicador: Elsevier
Tipo: Artigo de Revista Científica
Publicado em //2015 ENG
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Perylene dyes comprising: (i) 4-alkoxyphenylamino moiety in the 9-position as a strong donating group, (ii) cyanoacrylic acid as electron acceptor and anchoring group and (iii) a triple bond as short and rigid linker between perylene core and the acceptor group have been successfully synthesized. Their photophysical (i.e. absorption and emission spectra, molar extinction coefficients, fluorescence quantum yields and lifetime measurements) and electrochemical properties were investigated. The dyes display intense absorption in the visible exhibit high molar absorption coefficients making them good light harvesting materials for ss-DSCs.

A study of the elemental reactions involved in the initiation of the polymerization of tetrahydrofuran induced by the photosensitization of a triphenylsulphonium salt by perylene

Neumann,Miguel G.; Rodrigues,Maira R.
Fonte: Sociedade Brasileira de Química Publicador: Sociedade Brasileira de Química
Tipo: Artigo de Revista Científica Formato: text/html
Publicado em 01/01/2003 EN
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The photopolymerization of THF was studied in the presence of a triphenylsulphonium salt and perylene. The mechanism involves an electron transfer from the excited singlet state of perylene to triphenylsulphonium ions, resulting in perylene cation radicals that react with tetrahydrofuran. The calculated apparent yield of cation radicals follows the same general trend than the measured polymerization rates.

Fluorescence resonance energy transfer from pyrene to perylene labels for nucleic acid hybridization assays under homogeneous solution conditions

Masuko, Masayuki; Ohuchi, Shohkichi; Sode, Koji; Ohtani, Hiroyuki; Shimadzu, Akira
Fonte: Oxford University Press Publicador: Oxford University Press
Tipo: Artigo de Revista Científica
Publicado em 15/04/2000 EN
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We characterized the fluorescence resonance energy transfer (FRET) from pyrene (donor) to perylene (acceptor) for nucleic acid assays under homogeneous solution conditions. We used the hybridization between a target 32mer and its complementary two sequential 16mer deoxyribonucleotides whose neighboring terminals were each respectively labeled with a pyrene and a perylene residue. A transfer efficiency of ~100% was attained upon the hybridization when observing perylene fluorescence at 459 nm with 347-nm excitation of a pyrene absorption peak. The Förster distance between two dye residues was 22.3 Å (the orientation factor of 2/3). We could change the distance between the residues by inserting various numbers of nucleotides into the center of the target, thus creating a gap between the dye residues on a hybrid. Assuming that the number of inserted nucleotides is proportional to the distance between the dye residues, the energy transfer efficiency versus number of inserted nucleotides strictly obeyed the Förster theory. The mean inter-nucleotide distance of the single-stranded portion was estimated to be 2.1 Å. Comparison between the fluorescent properties of a pyrene–perylene pair with those of a widely used fluorescein–rhodamine pair showed that the pyrene–perylene FRET is suitable for hybridization assays.

Studies of archaebacterial bipolar tetraether liposomes by perylene fluorescence.

Khan, T K; Chong, P L
Fonte: PubMed Publicador: PubMed
Tipo: Artigo de Revista Científica
Publicado em /03/2000 EN
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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...

MAJOR PRODUCTS IN THE PHOTOCHEMISTRY OF PERYLENE ADSORBED IN MODELS OF ATMOSPHERIC PARTICULATE MATTER

Sotero, Pura; Arce, Rafael
Fonte: PubMed Publicador: PubMed
Tipo: Artigo de Revista Científica
Publicado em 05/09/2008 EN
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The photodegradation of adsorbed perylene is strongly influenced by the environment in which it is found as demonstrated by the nature of the photoproducts characterized on the adsorbed state in comparison to its photochemical behavior in solution. The separation, characterization, and identification of the products were carried out using HPLC equipped with UV-Vis diode array and MS detection. Two of the products were identified as 1,12-perylenedione and 3,10-perylenedione. Three additional products were characterized as a perylenedione and two perylenediols based on their m/z ratio. Based on this information, two possible mechanisms of formation were proposed for the identified diones. The experimental data showed that both the radical cation and singlet oxygen participate in the route of photodegradation of perylene which occurs through a mixed Type I and Type II pathway. These results assist in the understanding of complex processes undergone by perylene and other PAHs in the environment.

Molecular Dynamics Simulations of Perylene and Tetracene Librations: Comparison With Femtosecond Upconversion Data

Rosales, Tilman; Xu, Jianhua; Wu, Xiongwu; Hodoscek, Milan; Callis, Patrik; Brooks, Bernard R.; Knutson, Jay R.
Fonte: PubMed Publicador: PubMed
Tipo: Artigo de Revista Científica
EN
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In a prior manuscript by Xu et al. [Xu, J.; Shen, X.; Knutson, J. R. J. Phys. Chem. A 2003, 107, 8383], time-resolved fluorescence emission anisotropy measurements were performed on perylene and tetracene in hexadecane using an upconversion technique with ~100 fs resolution. The anisotropy transients contained previously unseen decay terms of ~300 fs. In perylene, their amplitude corresponded to the “ro defect” that has gathered interest over decades. We ascribed this term to a predominantly in-plane libration. In this manuscript, we present molecular dynamics simulations for the motions of perylene and tetracene using the CHARMm molecular dynamics program (version c29b2). Both rotational correlation functions contain subpicosecond decay terms that resemble experimental anisotropy decays. It was suggested that the ro defect might arise from excited-state distortions of perylene, so we conducted quantum mechanical calculations to show that such distortion does not significantly displace the oscillators. We compare the case of perylene, with a strongly allowed singlet emission transition, to that of the weakly allowed tetracene transition. In perylene, motion alone can explain subpicosecond anisotropy decay, while tetracene decay also contains vibrational coupling terms...

Rapid genotyping using pyrene−perylene locked nucleic acid complexes

Kumar, T. Santhosh; Myznikova, Anna; Samokhina, Evgeniya; Astakhova, Irina Kira
Fonte: Landes Bioscience Publicador: Landes Bioscience
Tipo: Artigo de Revista Científica
EN
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We have developed an assay for single strand DNA and RNA detection which is based on novel pyrene−perylene FRET pairs attached to short LNA/DNA probes. The assay is based on ratiometric emission upon binding of target DNA/RNA by three combinations of fluorescent LNA/DNA reporter strands. Specific geometry of the pyrene fluorophore attached to the 2′-amino group of 2′-amino-LNA in position 4 allows for the first time to efficiently utilize dipole−dipole orientation parameter for sensing of single-nucleotide polymorphisms (SNPs) in nucleic acid targets by FRET. Using novel probes, SNP detection is achieved with advantages of large Stokes shift (115 nm), high fluorescence quantum yields and low limit of target detection values (< 5 nM). Rapid and accurate genotyping of highly polymorphic HIV Pol cDNA and RNA fragments performed herein proves the possibility for broad application of the novel pyrene−perylene FRET pairs, e.g., in imaging and clinical diagnostics.

Effect of the Ortho Alkylation of Perylene Bisimides on the Alignment and Self-Assembly Properties

Dasgupta, Debarshi; Kendhale, Amol M; Debije, Michael G; ter Schiphorst, Jeroen; Shishmanova, Ivelina K; Portale, Giuseppe; Schenning, Albertus P H J
Fonte: Blackwell Publishing Ltd Publicador: Blackwell Publishing Ltd
Tipo: Artigo de Revista Científica
EN
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The effect of the ortho alkylation of perylene bisimides on the alignment and self-assembly properties has been studied. It was found that the dichroic properties of perylene bisimides in a liquid crystal host can be reversed with a single synthetic step by ortho alkylation. Furthermore, a solvent-induced growth of ultralong organic n-type semiconducting fibrils from non-ortho-alkylated perylene bisimide was observed. Ortho substitution of the perylene bisimide core alters the mode of fibrillar growth, leading to isotropic crystallization.

Highly Soluble Monoamino-Substituted Perylene Tetracarboxylic Dianhydrides: Synthesis, Optical and Electrochemical Properties

Chen, Kew-Yu; Chang, Che-Wei
Fonte: MDPI Publicador: MDPI
Tipo: Artigo de Revista Científica
Publicado em 08/12/2014 EN
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Three dialkylamino-substituted perylene tetracarboxylic dianhydrides with different n-alkyl chain lengths (n = 6, 12 or 18), 1a–1c, were synthesized under mild conditions in high yields and were characterized by 1H NMR, 13C NMR and high resolution mass spectroscopy. Their optical and electrochemical properties were measured using UV-Vis and emission spectroscopic techniques, as well as cyclic voltammetry (CV). This is the first time that the structures and the properties of monoamino-substituted perylene tetracarboxylic dianhydrides have been reported. These molecules show a deep green color in both solution and the solid state and are soluble in most organic solvents. They all show a unique charge transfer emission in the near-infrared region, and the associated peaks exhibit solvatochromism. The dipole moments of the compounds have been estimated using the Lippert-Mataga equation, and upon excitation, they show slightly larger dipole moment changes than those of corresponding perylene diimides, 2a–2c. Additionally, Compounds 1a–1c undergo two quasi-reversible one-electron oxidations and two quasi-reversible one-electron reductions in dichloromethane at modest potentials. Complementary density functional theory calculations performed on these chromophores are reported in order to gain more insight into their molecular structures and optical properties.

Perylene derivatives in biological systems: application as fluorescent probes in models for nanotechnology

BORIONI, SILVIA
Fonte: La Sapienza Universidade de Roma Publicador: La Sapienza Universidade de Roma
Tipo: Tese de Doutorado
EN
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Dimension Controlled Self-Assembly of Perylene Based Molecules

Sayyad, Arshad S.
Fonte: Universidade Rice Publicador: Universidade Rice
ENG
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Recent advances in the self-assembly of highly organized structures of organic semiconducting molecules by controlled non-covalent interactions has opened avenues for creating materials with unique optical and electrical properties. The main focus of this thesis lies in the synthesis and self-assembly of n-type perylene based organic semiconducting molecules into highly organized materials. Perylene based molecules used in this study are perylene diimide (PTCDI, two side-chains), perylene mono imide (m-PTCI, one side-chain), perylene tetracarboxylic acid (PTCA, no side-chain) and tetra-alkali metal salts of PTCA (M 4 -PTCA, no side-chain), which are synthesized from the parent perylene tetracarboxylic dianhydride (PTCDA). The self-assembly of these molecules have been performed using solution processing methods (dispersion, phase-transfer, and phase-transfer at high temperature) by taking advantage of the changes in solubility of the molecules, wherein the molecular interactions are maximized to favorably allow for the formation of highly organized structures. Dimension control (1D, 2D and 3D structures) of self-assembly has been obtained for different perylene based molecules by appropriate design of the molecule followed by controlling the conditions of assembly. In case of PTCDI...

Mise en place de l'expérience d'absorption transitoire femtoseconde et son application sur des dérivés du pérylène diimide

Karsenti, Paul-Ludovic
Fonte: Université de Montréal Publicador: Université de Montréal
Tipo: Thèse ou Mémoire numérique / Electronic Thesis or Dissertation
FR
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Mémoire numérisé par la Division de la gestion de documents et des archives de l'Université de Montréal

Influence of emitter orientation in perylene based OLEDs; Influência da orientação do emissor em OLEDs baseados em perileno

Sykora, Benedikt Reinhold
Fonte: Universidade de Aveiro Publicador: Universidade de Aveiro
Tipo: Dissertação de Mestrado
ENG
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Os díodos orgânicos emissores de luz (organic light-emitting diodes ou OLEDs) têm como elemento funcional um filme fino de um semicondutor orgânico para a criação de excitões (pares electrão-lacuna), que emitem luz quando relaxam. O objetivo desta dissertação de mestrado é investigar o efeito da orientação dipolar de filmes baseados em perilenos de tetraphenyldibenzoperiflanthene (DBP) e diindenoperylene ( DIP), e das mesmas moléculas dispersas numa ma matriz de 5,6,11,12- tetraphenylnaphthacene (rubreno). O estudo tenta identificar uma possível relação entre o comportamento destes filmes e a eficiência do respetivo OLED. Observa-se que os filmes de DBP são amorfos, apresentam uma superfície lisa e absorvem mais luz do que os filmes de DIP, que se caracterizam por uma estrutura cristalina e uma superfície irregular. Os resultados combinados de simulações e de medições de fotoluminescência com dependência angular revelam que as moléculas de DBP apresentam orientação horizontal, estando as moléculas de DIP orientadas verticalmente. Este facto pode explicar o acoplamento mais forte das moléculas de DIP aos plasmões de superfície, em comparação com o DBP. As características gerais dos filmes de DBP ou DIP mantêm-se mesmo quando estes são depositados nos substratos de N...