Search results for "PERYLENE"
showing 10 items of 70 documents
Sensitization of nanocrystalline TiO2 with 3,4,9,10-perylene tetracarboxylic acid
2014
Optical properties of 3,4,9,10-perylene tetracarboxylic acid (PTCA) in the presence of nanocrystalline TiO2 (nominal diameter 15 nm) have been investigated in ethanol solution and in the solid state by UV-Vis absorption spectroscopy and steady-state and time-resolved fluorescence. Experimental results show that, in ethanol, the presence of TiO2 nanoparticles causes significant changes in the typical absorption and fluorescence bands of PTCA and in the fluorescence relaxation time. Similar effects are also detected in solid samples, obtained by electrospray deposition technique. The nonlinear optical properties of the PTCA-TiO2 in ethanol solutions were investigated using the single-beam Z-s…
Diastereoselective formation of homochiral flexible perylene bisimide cyclophanes and their hybrids with fullerenes†‡
2021
Cyclophanes of different ring sizes featuring perylene-3,4:9,10-tetracarboxylic acid bisimide (PBI) linked by flexible malonates were designed, synthesized, and investigated with respect to their structural, chemical and photo-physical properties. It is predominantly the number of PBIs and their geometric arrangement, which influence dramatically their properties. For example, two-PBI containing cyclophanes reveal physico-chemical characteristics that are governed by strong co-facial π–π interactions. This is in stark contrast to cyclophanes with either three or four PBIs. Key to co-facial π–π stackings are the flexible malonate linkers, which, in turn, set up the ways and means for diaster…
Effect of Substituents at Imide Positions on the Laser Performance of 1,7-Bay-Substituted Perylenediimide Dyes
2021
Perylenediimide (PDI) compounds with no substituents in their core are widely used as the active units of thin-film organic lasers. Recently, bay-substituted PDIs (b-PDIs) bearing two sterically hindering diphenylphenoxy groups at the 1,7-bay positions have received great attention because they show red-shifted emission with respect to bay-unsubstituted PDIs, while maintaining high photoluminescence (PL) quantum yields and low amplified spontaneous emission (ASE) thresholds even at high doping rates. However, their ASE photostability is relatively low compared to that of state-of-the-art PDIs. Thus, the design of b-PDIs with improved ASE photostability remains a challenge. Here, the synthes…
Insights into the anion effect on the self assembly of perylene bisimide diimidazolium salts
2017
Abstract We studied how changing the anion affects the self-assembly of three diimidazolium salts bearing a perylene bisimide spacer. In particular we used [BF 4 − ] and [NTf 2 − ] based salts together with a mixed salt bearing both [I − ] and [BF 4 − ] anions. Thermal as well as concentration and temperature dependent spectroscopic investigations revealed that changing the anion impacts on solid state and solution aggregation, leading to articulate thermotropic behaviors and contrasting solvent effects, respectively. We also studied the electrochemical behavior of the salts to verify if changing the anion alters the redox properties of the salts. Finally, different anions also lead to very…
Kinetically Trapped Supramolecular Assembly of Perylene Dianhydride Derivative in Methanol: Optical Spectra, Morphology, and Mechanisms.
2016
Supramolecular self-assembly has attracted increasing attention as a breakthrough methodology in the fields of nanoscience and nanotechnology. Herein, a perylene dianhydride derivative (TP-PDA) self-assembles into well-defined nanospheres through a nucleation-growth process. The mechanisms of this process were explored by using spectral analysis, dynamic light scattering (DLS), and scanning electron microscopy (SEM). In situ DLS and in situ SEM both revealed that the size of the aggregated nanospheres increases with time until the formation of equilibrium H-aggregates. This shows that TP-PDA undergoes a kinetically trapped assembly with a rapid transformation into the thermodynamically favo…
Bias and humidity effects on the ammonia sensing of perylene derivative/lutetium bisphthalocyanine MSDI heterojunctions
2016
International audience; In this paper, we prepared and studied sensors based on Molecular Semiconductor-Doped Insulator (MSDI) heterojunctions. These original devices are built with two stacked layers of molecular materials and exhibit very specific electrical and sensing properties. We studied the properties of a MSDI composed of the perylenetetracarboxylic dianhydride, PTCDA, or the fluorinated perylenebisimine derivative, C4F7-PTCDI, as n-type molecular material sublayers, and LuPc2 as a p-type semiconductor top layer. Their response to ammonia was compared to that of a resistor formed of only the top layer of the MSDI (LuPc2). Ammonia increases the current in the MSDIs whereas it causes…
Microsomal Biotransformation of Benzo[ghi]perylene, a Mutagenic Polycyclic Aromatic Hydrocarbon without a “Classic” Bay Region
2005
Carcinogenic polycyclic aromatic hydrocarbons (PAH), e.g., benzo[a]pyrene (BaP), possess a bay region comprising an ortho-fused benzene ring. Benzo[ghi]perylene (BghiP) represents the group of PAHs lacking such a "classic" bay region and hence cannot be metabolically converted like BaP to bay region dihydrodiol epoxides considered as ultimate mutagenic and carcinogenic metabolites of PAH. BghiP exhibits bacterial mutagenicity in strains TA98 (1.3 his(+)-revertant colonies/nmol) and TA100 (4.3 his(+)-revertant colonies/nmol) of Salmonella typhimurium after metabolic activation by the postmitochondrial hepatic fraction of CD rats treated with 3-methylcholanthrene. Inhibition of microsomal epo…
The 3,4-oxide is responsible for the DNA binding of benzo[ghi]perylene, a polycyclic aromatic hydrocarbon without a “classic” bay-region
2008
Abstract The polycyclic aromatic hydrocarbon (PAH) benzo[ghi]perylene (BghiP) lacks a “classic” bay-region and is therefore unable to form vicinal dihydrodiol epoxides thought to be responsible for the genotoxicity of carcinogenic PAHs like benzo[a]pyrene. The bacterial mutagenicity of BghiP increases considerably after inhibition of the microsomal epoxide hydrolase (mEH) indicating arene oxides as genotoxic metabolites. Two K-region epoxides of BghiP, 3,4-epoxy-3,4-dihydro-BghiP (3,4-oxide) and 3,4,11,12-bisepoxy-3,4,11,12-tetrahydro-BghiP (3,4,11,12-bisoxide) identified in microsomal incubations of BghiP are weak bacterial mutagens in strain TA98 of Salmonella typhimurium with 5.5 and 1.5…
From anthraquinone to heterocoronene as stable red chromophore
2018
Using the commercially available 1,4,5,8-tetrachloroanthraquinone (1) as starting material, a N-heterocoronene derivative 3 was synthesized via a straightforward two-step reaction. Compound 3 shows a similar photostability as perylene dyes, qualifying it as a promising colorant.
Calculation of vibrationally resolved absorption and fluorescence spectra of the rylenes
2020
A generating function method was used to simulate the vibrationally resolved absorption and emission spectra of perylene, terrylene and quaterrylene. This method operates on the basis of adiabatic excitation energies and electronic ground and excited state vibrational frequencies. These parameters were calculated using density functional theory with the PBE0 functional for perylene and terrylene and with the BH-LYP functional for quaterrylene. The vertical excitation energies of the lower excited states were calculated using functionals with differing amounts of Hartree-Fock exchange. The optimal functional for each molecule was chosen by comparing these energies to literature excitation en…