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Artykuły w czasopismach na temat „Perylene”

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Autor: Grafiati

Data publikacji: 4 czerwca 2021

Data aktualizacji: 25 maja 2024

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1

Lentijo, S., J. E. Expósito, G. Aullón, J. A. Miguel i P. Espinet. "Highly fluorescent complexes with 3-isocyanoperylene and N-(2,5-di-tert-butylphenyl)-9-isocyano-perylene-3,4-dicarboximide". Dalton Trans. 43, nr 28 (2014): 10885–97. http://dx.doi.org/10.1039/c4dt01016g.

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2

Loewe, Robert S., Kin-ya Tomizaki, Fabien Chevalier i Jonathan S. Lindsey. "Synthesis of perylene-porphyrin dyads for light-harvesting studies". Journal of Porphyrins and Phthalocyanines 06, nr 10 (październik 2002): 626–42. http://dx.doi.org/10.1142/s1088424602000774.

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The spectral coverage of porphyrin-based light-harvesting arrays can be enhanced through the use of suitable accessory pigments. Perylene-monoimide dyes can serve as valuable accessory pigments with porphyrins. To investigate the choice of perylene-monoimide and the effects of molecular architecture on light-harvesting efficacy, five perylene-porphyrin dyads were prepared. Each dyad employs a diphenylethyne linker that bridges the perylene N-imide site and the porphyrin meso-position. Three dyads incorporate a mono-phenoxy perylene at the o-, m-, or p-position of the meso-aryl group on the porphyrin. The two remaining dyads incorporate a perylene-monoimide (bearing zero or three phenoxy substituents) at the p-position of the meso-aryl group on the porphyrin. The introduction of phenoxy groups on the perylenes increases the solubility, a key requirement for use in light-harvesting arrays. The long-wavelength absorption band of the perylene shifts from 506 nm to 532 or 533 nm upon substitution with one or three phenoxy groups, respectively. The synthesis of the dyads entails Pd -mediated coupling of a bromo-perylene and an ethynyl porphyrin, or the mixed-aldehyde condensation with a perylene-aldehyde, mesitaldehyde, and pyrrole. Five perylene-monoimide dyes bearing an ethyne or bromo substituent at the p-position of the N-aryl unit were developed for this modular chemistry. Each perylene-porphyrin dyad exhibits efficient energy transfer from the excited perylene to the ground-state porphyrin.

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3

Mauri, Luca, Alessia Colombo, Claudia Dragonetti, Francesco Fagnani i Dominique Roberto. "Iridium and Ruthenium Complexes Bearing Perylene Ligands". Molecules 27, nr 22 (16.11.2022): 7928. http://dx.doi.org/10.3390/molecules27227928.

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The present review summarizes the work carried out mostly in the last decade on iridium and ruthenium complexes bearing various perylene ligands, of particular interest for bioimaging, photodynamic therapy, and solar energy conversion. In these complexes, the absorption spectra and the electrochemical properties are those of the perylene subunit plus those of the metal moiety. In contrast, the emissions are completely changed with respect to perylenes considered alone. Thus, fully organic perylenes are characterized by a strong fluorescence in the visible region, lifetimes of a few nanoseconds, and luminescence quantum yields approaching 100%, whereas perylene Ir and Ru complexes usually do not emit; however, in few cases, weak phosphorescent emissions, with lifetimes in the range of microseconds and relatively low quantum yields, are reported. This is due to a strong interaction between the perylene core and the heavy metal center, taking place after the excitation. Nevertheless, an important advantage deriving from the presence of the heavy metal center is represented by the ability to generate large amounts of singlet oxygen, which plays a key role in photodynamic therapy.

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4

Nakano, Masahiro, Kyohei Nakano, Kazuo Takimiya i Keisuke Tajima. "Two isomeric perylenothiophene diimides: physicochemical properties and applications in organic semiconducting devices". Journal of Materials Chemistry C 7, nr 8 (2019): 2267–75. http://dx.doi.org/10.1039/c8tc05577g.

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Two thiophene-fused perylene-3,4,9,10-tetracarboxy diimides, peryleno[2,1-b]thiophene diimide (PTIa) and peryleno[1,2-b]thiophene diimide (PTIb), were synthesized as electron-deficient building units for electronic and optoelectronic materials.

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5

Gutman, Ivan, Boris Furtula, Jelena Djurdjevic, Rradmila Kovacevic i Sonja Stankovic. "Annelated perylenes: Benzenoid molecules violating the Kekulé-structure-based cyclic conjugation models". Journal of the Serbian Chemical Society 70, nr 8-9 (2005): 1023–32. http://dx.doi.org/10.2298/jsc0509023g.

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Several currently used models for assessing the extent of cyclic conjugation in benzenoid hydrocarbons, all based on Kekul?-type structural formulas predict that there is no cyclic conjugation in the central, "empty", ring of perylene and its annelated derivatives. In this paper it is shown that in some annelated perylenes the cyclic conjugation in the "empty" ring (measured by its energy-effect) may be unexpectedly high. Therefore, in the case of these annelated perylenes, the Kekul?- structure-based models fail. The cause for such an "anomalous" behavior of annelated perylenes is discussed.

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6

Duncan, Katelyn M., Donald L. Kellis, Jonathan S. Huff, Matthew S. Barclay, Jeunghoon Lee, Daniel B. Turner, Paul H. Davis, Bernard Yurke, William B. Knowlton i Ryan D. Pensack. "Symmetry Breaking Charge Transfer in DNA-Templated Perylene Dimer Aggregates". Molecules 27, nr 19 (5.10.2022): 6612. http://dx.doi.org/10.3390/molecules27196612.

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Molecular aggregates are of interest to a broad range of fields including light harvesting, organic optoelectronics, and nanoscale computing. In molecular aggregates, nonradiative decay pathways may emerge that were not present in the constituent molecules. Such nonradiative decay pathways may include singlet fission, excimer relaxation, and symmetry-breaking charge transfer. Singlet fission, sometimes referred to as excitation multiplication, is of great interest to the fields of energy conversion and quantum information. For example, endothermic singlet fission, which avoids energy loss, has been observed in covalently bound, linear perylene trimers and tetramers. In this work, the electronic structure and excited-state dynamics of dimers of a perylene derivative templated using DNA were investigated. Specifically, DNA Holliday junctions were used to template the aggregation of two perylene molecules covalently linked to a modified uracil nucleobase through an ethynyl group. The perylenes were templated in the form of monomer, transverse dimer, and adjacent dimer configurations. The electronic structure of the perylene monomers and dimers were characterized via steady-state absorption and fluorescence spectroscopy. Initial insights into their excited-state dynamics were gleaned from relative fluorescence intensity measurements, which indicated that a new nonradiative decay pathway emerges in the dimers. Femtosecond visible transient absorption spectroscopy was subsequently used to elucidate the excited-state dynamics. A new excited-state absorption feature grows in on the tens of picosecond timescale in the dimers, which is attributed to the formation of perylene anions and cations resulting from symmetry-breaking charge transfer. Given the close proximity required for symmetry-breaking charge transfer, the results shed promising light on the prospect of singlet fission in DNA-templated molecular aggregates.

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7

Fang, Xiangdong. "BN-Embedded Perylenes". Molecules 26, nr 23 (25.11.2021): 7148. http://dx.doi.org/10.3390/molecules26237148.

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Transition metal catalyzed coupling reaction strategy has been utilized in the synthesis of two novel BN-perylenes starting from halogenated BN-naphthalene derivatives. The molecular structures and packing modes of BN-perylenes were confirmed by NMR spectroscopy and X-ray single-crystal diffraction experiments. Their photophysical properties were further investigated using UV-vis and fluorescence spectroscopy and DFT calculations. Interestingly, the isosteric BN-insertion in perylene system resulted in stronger π-π stacking interaction both in solid and solution phases. The synthesized BN-perylenes are proved to be highly stable and thus provide a new valuable platform for novel organic materials applications which is otherwise inaccessible to date.

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8

Liu, Yu, Han Zhong, Yu Qin, Yan Zhang, Xinfeng Liu i Tao Zhang. "Non-covalent hydrophilization of reduced graphene oxide used as a paclitaxel vehicle". RSC Advances 6, nr 36 (2016): 30184–93. http://dx.doi.org/10.1039/c6ra04349f.

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Phosphorylcholine oligomer grafted perylene (Perylene-PCn) was synthesized. By π–π stacking interaction of reduced graphene oxide (RGO) and perylene moiety, water dispersible RGO/Perylene-PCn composites were prepared and used as paclitaxel vehicle.

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9

Nagasawa, Yuya, Takeshi Koyama i Susumu Okada. "Energetics and electronic structures of perylene confined in carbon nanotubes". Royal Society Open Science 5, nr 6 (czerwiec 2018): 180359. http://dx.doi.org/10.1098/rsos.180359.

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The energetics and geometries of perylene encapsulated in carbon nanotubes (CNTs) have been investigated employing density functional theory using the generalized gradient approximation combined with the van der Waals correction. Our calculations show that the encapsulated perylene molecules possess two metastable molecular conformations with respect to the CNT wall, which are almost degenerate with each other. A standing conformation, with respect to the CNT wall, is the ground state conformation for a semiconducting (19,0)CNT, while a lying conformation is the ground state for a metallic (11,11)CNT. Cooperation and competition between perylene–perylene and perylene–CNT interactions cause these possible perylene conformations inside CNTs. However, the electronic structure of the CNT encapsulating the perylene molecules is found to be insensitive to the molecular conformation.

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10

Cremer, Jens, i Peter Bäuerle. "Perylene-Oligothiophene-Perylene Triads for Photovoltaic Applications". European Journal of Organic Chemistry 2005, nr 17 (wrzesień 2005): 3715–23. http://dx.doi.org/10.1002/ejoc.200500147.

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11

Papadopoulos, Ilias, David Gutiérrez-Moreno, Yifan Bo, Rubén Casillas, Phillip M. Greißel, Timothy Clark, Fernando Fernández-Lázaro i Dirk M. Guldi. "Altering singlet fission pathways in perylene-dimers; perylene-diimide versus perylene-monoimide". Nanoscale 14, nr 13 (2022): 5194–203. http://dx.doi.org/10.1039/d1nr08523a.

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The inherent differences on coplanarity and dipole moment in perylene-monoimides versus perylene-diimides and their impact on the singlet fission process were investigated in a series of phenylene- and naphthalene-linked dimers.

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12

Suzuki, Akira, Munetaka Akita i Michito Yoshizawa. "Amphiphilic tribranched scaffolds with polyaromatic panels that wrap perylene stacks displaying unusual emissions". Chemical Communications 52, nr 65 (2016): 10024–27. http://dx.doi.org/10.1039/c6cc04823d.

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A spherical assembly containing a perylene stack, prepared from a rigid tribranched scaffold and perylene, exhibits unusual Y-emission in water at room temperature. In contrast, an analogous assembly from a flexible scaffold and perylene shows E-emission under the same conditions.

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13

Tucker, Sheryl A., William E. Acree, John C. Fetzer i Reginald H. Mitchell. "Polycyclic Aromatic Hydrocarbon Solute Probes. Part X: Evaluation of Select Hydrogenated Pyrene, Benzo[ghi]perylene, and Naphthacene Derivatives as Possible Solvent Polarity Probes". Applied Spectroscopy 47, nr 7 (lipiec 1993): 1040–45. http://dx.doi.org/10.1366/0003702934415200.

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Fluorescence emission spectra are reported for 3,4,5-trihydrobenzo[cd]pyrene, 3,4-dihydrobenzo[ghi]perylene, 5,6,7,8,9,10-hexahydrobenzo[ghi]perylene, trans-10b,10c-dihydro-10b,10c-dimethylpyrene, trans-12b,12c-dihydro-12b,12c-dimethylbenzo[a]pyrene, and trans-14b,14c-dihydro-14b,14c-dimethylnaphtho[2,1,8-qra]naphthacene dissolved in organic nonelectrolyte solvents of varying polarity. Dihydrobenzo|ghi]perylene was found to exhibit probe character, as evidenced by a systematic variation in emission intensity ratio with solvent polarity. It has a dynamic range of 0.98 and a high fluorescence quantum yield and is thought to be noncarcinogenic. Also reported are mathematical expressions which correlate measured intensity ratios and solvent polarity probe behavior of dihydrobenzo[ghi]perylene, pyrene, benzo[ghi]perylene, coronene, and ovalene in 48 solvents of varying polarity.

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14

Wojciechowski, Jonathan P., Adam D. Martin, Mohan Bhadbhade, James E. A. Webb i Pall Thordarson. "Halogen bonding influences perylene-core twists in non-core substituted perylene tetraesters". CrystEngComm 18, nr 24 (2016): 4513–17. http://dx.doi.org/10.1039/c6ce00929h.

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15

Almuhana, Asia R. Y., Philipp Langer, Sarah L. Griffin, Rhys W. Lodge, Graham A. Rance i Neil R. Champness. "Retention of perylene diimide optical properties in solid-state materials through tethering to nanodiamonds". Journal of Materials Chemistry C 9, nr 32 (2021): 10317–23. http://dx.doi.org/10.1039/d1tc02577e.

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16

Wangatia, Lodrick Makokha, Bin Sun, Ting Zeng i Meifang Zhu. "Reactive bay functionalized perylene monoimide-polyhedral oligomeric silsesquioxane organic electronic dye". Materials Science-Poland 33, nr 1 (1.03.2015): 113–21. http://dx.doi.org/10.1515/msp-2015-0016.

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AbstractAggregation-induced quenching is particularly detrimental in perylene diimides, which are characterized by a near-unity fluorescence quantum yield in solution but are far less emissive in the solid state. Previously, perylene diimide has been improved by linking it to the inorganic cage of polyhedral oligomeric silsesquioxanes. As a further study on perylene diimidepolyhedral oligomeric silsesquioxanes, we report on a double functionalized molecular structure, which can be used for substitution at the bay area and as a side group in other materials. Typical solution absorption and emission features of the perylene diimide fragment have been observed in this new reactive perylene diimide-polyhedral oligomeric silsesquioxane. Moreover, reduced stacking during aggregation and spherical particles exhibiting solid fluorescence have been obtained. Organic semiconducting material with enhanced solid state photophysical properties, like solid fluorescence is a subject of great interest owing to its possible high-tech applications in optoelectronic devices.

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17

Deng, Qingyuan, Enbao Zhou, Yongwei Huang, Weixia Qing, Haiyan Zhai, Zhonghua Liu i Zhixiang Wei. "Chalcogen-substitution modulated supramolecular chirality and gas sensing properties in perylenediimides". Chemical Communications 55, nr 30 (2019): 4379–82. http://dx.doi.org/10.1039/c9cc01443h.

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18

Wang, Gang, Weina Wang, Rong Miao, Congdi Shang, Meixia He, Haonan Peng, Gang He i Yu Fang. "A perylene bisimide derivative with pyrene and cholesterol as modifying structures: synthesis and fluorescence behavior". Physical Chemistry Chemical Physics 18, nr 17 (2016): 12221–30. http://dx.doi.org/10.1039/c6cp01447j.

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19

Kozma, E., W. Mróz, A. Andicsová Eckstein, V. Lukeš, F. Galeotti, A. Šišková, M. Danko i M. Catellani. "A joint experimental and theoretical study on the electro-optical properties of 1,6- and 1,7-fluorenyl disubstituted perylene diimide isomers". New Journal of Chemistry 42, nr 2 (2018): 1061–66. http://dx.doi.org/10.1039/c7nj03860g.

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20

Xu, Xu, Yuqi Li, Zhongqiang Xiong, Jin Yang, Lulu Pan, Yunyun Wu, Chun Wei i Shaorong Lu. "Preparation and model of high-performance shape-memory polyurethane with hydroxylated perylene bisimide". RSC Advances 6, nr 111 (2016): 110329–36. http://dx.doi.org/10.1039/c6ra24393b.

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21

Draper, Emily R., James J. Walsh, Tom O. McDonald, Martijn A. Zwijnenburg, Petra J. Cameron, Alexander J. Cowan i Dave J. Adams. "Air-stable photoconductive films formed from perylene bisimide gelators". J. Mater. Chem. C 2, nr 28 (2014): 5570–75. http://dx.doi.org/10.1039/c4tc00744a.

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22

Schmidt, Rüdiger, Peter Osswald, Martin Könemann i Frank Würthner. "Synthetic Routes to Core-fluorinated Perylene Bisimide Dyes and their Properties". Zeitschrift für Naturforschung B 64, nr 6 (1.06.2009): 735–46. http://dx.doi.org/10.1515/znb-2009-0621.

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Numerous core-fluorinated perylene bisimide (PBI) dyes with various substituents at the imide positions have been synthesized by different methods. Core-difluorinated PBIs 4a-f are obtained by imidization of difluoro-substituted perylene bisanhydride 1 with appropriate primary amines or, alternatively, by nucleophilic halogen exchange reactions (Halex process) of the corresponding dibromosubstituted PBIs 2a-d,f with potassium fluoride. Core-tetrafluorinated PBIs 5a-c could also be synthesized by halogen exchange reactions of the respective tetrachlorinated PBIs 3a-c. In particular, core-fluorinated perylene bisimide pigments 4h, 5h containing hydrogen atoms in the imide positions could be obtained for the first time by deprotection of α-methylbenzyl-substituted precursors. Compared with core-unsubstituted perylene bisimides, these fluorinated dyes display hypsochromically shifted absorption and fluorescence spectra, and they exhibit fluorescence quantum yields up to unity, enabling bright yellow emission. The electrochemical properties of these electron-poor perylene bisimides have been studied. Furthermore, the packing features of a tetrafluorinated PBI derivative in the solid state have been discussed.

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23

Niide, Teppei, Kyohei Ozawa, Hikaru Nakazawa, Daniel Oliveira, Hitoshi Kasai, Mari Onodera, Ryutaro Asano, Izumi Kumagai i Mitsuo Umetsu. "Organic crystal-binding peptides: morphology control and one-pot formation of protein-displaying organic crystals". Nanoscale 7, nr 47 (2015): 20155–63. http://dx.doi.org/10.1039/c5nr06471f.

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24

Kozlov, A. V., L. R. Sizov, D. V. Revina, A. Yu Rybkin i N. S. Goryachev. "Photophysical and Photochemical Properties of Perylene–(Cyanine Dye) Dyad in the VIS–NIR Spectrum Region". Журнал физической химии 97, nr 5 (1.05.2023): 602–6. http://dx.doi.org/10.31857/s0044453723050138.

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The photophysical properties of an original covalently-bonded dyad based on a perylene derivative and IR-780 cyanine dye were studied. The dyad has pronounced absorption in the NIR region of the spectrum and a strong fluorescence signal, which is weakly quenched by the influence of the perylene derivative. Upon excitation of the dyad in the absorption region of perylene, a fluorescence signal from IR-780 is detected due to the Förster energy transfer mechanism. It is shown that the dyad does not generate singlet oxygen upon photoexcitation in the NIR region of the spectrum. However, it can generate superoxide anion radicals, indicating the presence of the photoinduced electrons transfer from the dye to the perylene.

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25

Yang, X., H. J. Räder, A. Rouhanipour i K. Müllen. "Soft Deposition of Organic Macromolecules with Fast Atom Bombardment Mass Spectrometry". European Journal of Mass Spectrometry 11, nr 3 (czerwiec 2005): 287–93. http://dx.doi.org/10.1255/ejms.762.

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In order to investigate the requirements for soft deposition of intact positively charged organic macromolecules, an homogenous series of modal compounds such as polyphenylene dendronized perylenes (PDPs), C80H52, C200H132 and C320H212 and a series of derivatives involving perylene derivative, C98H104N8O4, terrylene derivative, C78H82N6O4 and quaterrylene derivative, C140H138N10O8, were used for soft-landing experiments on a metallic or matrix coated surface using fast atom bombardment mass spectrometry. Soft-landing can be achieved at impact energies below 180 eV with no production of fragments. The deposition rate shows strong energy dependence with similar behavior of the different organic compounds. A single isotope of the molecule was selected and soft-landed at increased resolution.

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26

Yang, Lin, Shu Chen, Jing Zhang, Junting Wang, Min Zhang, Xiandui Dong i Peng Wang. "Judicious engineering of a metal-free perylene dye for high-efficiency dye sensitized solar cells: the control of excited state and charge carrier dynamics". Journal of Materials Chemistry A 5, nr 7 (2017): 3514–22. http://dx.doi.org/10.1039/c6ta10506h.

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27

Kohl, Miroslav, Fouzy Alafid, Marek Bouška, Anna Krejčová, Yash Raycha, Andréa Kalendová, Radim Hrdina i Ladislav Burgert. "New Corrosion Inhibitors Based on Perylene Units in Epoxy Ester Resin Coatings". Coatings 12, nr 7 (29.06.2022): 923. http://dx.doi.org/10.3390/coatings12070923.

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Four new compounds from perylene dianhydride were prepared and tested for their anti-corrosion properties. Dizinc salt of perylene-3,4,9,10-tetracarboxylic acid and dimagnesium salts of perylene-3,4,9,10-tetracarboxylic acid, 5,5′-(1,3,8,10-tetraoxo-1,3,8,10-tetrahydroanthra[2,1,9-def:6,5,10-d′e′f′] diisoquinoline-2,9-diyl) bis(2-hydroxybenzoic acid) and N,N′-bis[3,3′-(dimethylamino)propylamine]-3,4,9,10-perylenediimide were characterized by analytical methods (SEM, EDX, X-ray) and parameters used in the field of paints (density, oil number and critical volume concentrations of pigment). The pigments (in a pigment volume concentration series) were used to prepare paints also containing a perylene C26H14N2O4 (Compound I) derivative pigment plus inert titanium dioxide to maintain a constant concentration of solids in the paint film. A mixture containing zinc nitroisophthalate and both the perylene derivative and titanium dioxide served as the reference material. The paints were applied to steel panels in two layers with a ruler. The organic coatings were subjected to electrochemical measurements and accelerated cyclic corrosion tests. The highest corrosion resistance was found for the coating containing C24H8O8Mg2. Superior to the coating containing either C26H14N2O4 or the conventional corrosion inhibitor C8H5N06-Zn, this pigment type acted mainly by a mechanism based on the compound’s complexation capacity at the metallic surface/organic coating/corrosion medium interface. The organic coatings containing perylene acid salts also attained high mechanical resistance.

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Leowanawat, Pawaret, Agnieszka Nowak-Król i Frank Würthner. "Tetramethoxy-bay-substituted perylene bisimides by copper-mediated cross-coupling". Organic Chemistry Frontiers 3, nr 5 (2016): 537–44. http://dx.doi.org/10.1039/c6qo00047a.

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CuBr-mediated cross-coupling of 1,6,7,12-tetrabromo-perylene-3,4,9,10-tetracarboxylic acid ester or bis(dicarboximide) with NaOMe affords the respective tetramethoxy-perylene derivatives which are excellent green and red emitters.

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29

Sun, Yan, Tongfei Zuo, Fang Guo, Jing Sun, Ziwei Liu i Guowang Diao. "Perylene dye-functionalized silver nanoparticles serving as pH-dependent metal sensor systems". RSC Advances 7, nr 39 (2017): 24215–20. http://dx.doi.org/10.1039/c7ra03264a.

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Lysine-functionalized perylene was used to modify nanoparticles. Due to the benefits from a synergetic effect that originated between the perylene and silver nanoparticles, color-based metal sensor systems were established.

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30

Ventura, Barbara, Heinz Langhals, Bernd Böck i Lucia Flamigni. "Phosphorescent perylene imides". Chemical Communications 48, nr 35 (2012): 4226. http://dx.doi.org/10.1039/c2cc30948c.

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31

Swager, Timothy, i Kosuke Yoshinaga. "Fluorofluorescent Perylene Bisimides". Synlett 29, nr 19 (31.07.2018): 2509–14. http://dx.doi.org/10.1055/s-0037-1610224.

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Perfluorinated liquids can exhibit immiscibility with organic solvents and water, and provide orthogonal opportunities in chemistry. Examples of emissive dyes that display only fluorous phase solubility are limited, despite the many potential applications. Perylene bisimides are among the most versatile dyes and are known for their outstanding stability and high quantum yields. Herein, we report the synthesis of two new “fluorofluorescent” perylene bisimide dyes, designed to be soluble in the fluorous phases. These two dyes possess unique photophysical properties, including dramatic increases in fluorescence quantum yields when treated with Brønsted acids as well as aggregation in the fluorous phase.

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32

Markoulides, Marios S., Chiara Venturini, David Neumeyer i André Gourdon. "Oxidative cyclodehydrogenation of a perylene derivative: different reagents give different products". New Journal of Chemistry 39, nr 8 (2015): 6498–503. http://dx.doi.org/10.1039/c5nj00808e.

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Oxidative cyclodehydrogenation of 3-(4-fluoronaphthalen-1-yl)perylene gives, by reaction with AlCl₃, 3-fluoroterrylene and by reaction with DDQ/TfOH, its isomer 10-fluorobenzo[4,5]indeno[1,2,3-cd]perylene.

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33

Baba, Koichi, Sayaka Konta, Daniel Oliveira, Kenji Sugai, Tsunenobu Onodera, Akito Masuhara, Hitoshi Kasai, Hidetoshi Oikawa i Hachiro Nakanishi. "Perylene and Perylene-Derivative Nano-Cocrystals: Preparation and Physicochemical Property". Japanese Journal of Applied Physics 51 (19.11.2012): 125201. http://dx.doi.org/10.1143/jjap.51.125201.

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34

Baba, Koichi, Sayaka Konta, Daniel Oliveira, Kenji Sugai, Tsunenobu Onodera, Akito Masuhara, Hitoshi Kasai, Hidetoshi Oikawa i Hachiro Nakanishi. "Perylene and Perylene-Derivative Nano-Cocrystals: Preparation and Physicochemical Property". Japanese Journal of Applied Physics 51, nr 12R (1.12.2012): 125201. http://dx.doi.org/10.7567/jjap.51.125201.

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Mikhnovets, Igor E., Jiří Holoubek, Irina S. Panina, Jan Kotouček, Daniil A. Gvozdev, Stepan P. Chumakov, Maxim S. Krasilnikov i in. "Alkyl Derivatives of Perylene Photosensitizing Antivirals: Towards Understanding the Influence of Lipophilicity". International Journal of Molecular Sciences 24, nr 22 (18.11.2023): 16483. http://dx.doi.org/10.3390/ijms242216483.

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Amphipathic perylene derivatives are broad-spectrum antivirals against enveloped viruses that act as fusion inhibitors in a light-dependent manner. The compounds target the lipid bilayer of the viral envelope using the lipophilic perylene moiety and photogenerating singlet oxygen, thereby causing damage to unsaturated lipids. Previous studies show that variation of the polar part of the molecule is important for antiviral activity. Here, we report modification of the lipophilic part of the molecule, perylene, by the introduction of 4-, 8-, and 12-carbon alkyls into position 9(10) of the perylene residue. Using Friedel–Crafts acylation and Wolff–Kishner reduction, three 3-acetyl-9(10)-alkylperylenes were synthesized from perylene and used to prepare 9 nucleoside and 12 non-nucleoside amphipathic derivatives. These compounds were characterized as fluorophores and singlet oxygen generators, as well as tested as antivirals against herpes virus-1 (HSV-1) and vesicular stomatitis virus (VSV), both known for causing superficial skin/mucosa lesions and thus serving as suitable candidates for photodynamic therapy. The results suggest that derivatives with a short alkyl chain (butyl) have strong antiviral activity, whereas the introduction of longer alkyl substituents (n = 8 and 12) to the perylenyethynyl scaffold results in a dramatic reduction of antiviral activity. This phenomenon is likely attributable to the increased lipophilicity of the compounds and their ability to form insoluble aggregates. Moreover, molecular dynamic studies revealed that alkylated perylene derivatives are predominately located closer to the middle of the bilayer compared to non-alkylated derivatives. The predicted probability of superficial positioning correlated with antiviral activity, suggesting that singlet oxygen generation is achieved in the subsurface layer of the membrane, where the perylene group is more accessible to dissolved oxygen.

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36

Ahmad, Shargeel, Jinxuan Liu, Wei Ji i Licheng Sun. "Metal–Organic Framework Thin Film-Based Dye Sensitized Solar Cells with Enhanced Photocurrent". Materials 11, nr 10 (1.10.2018): 1868. http://dx.doi.org/10.3390/ma11101868.

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Metal–organic framework thin film-based dye sensitized solar cell is fabricated with highly oriented, crystalline, and porous Zn-perylene metal-organic framework (MOF) thin film (SURMOF) which is integrated with Bodipy embedded in poly(methyl methacrylate). It has been demonstrated that the photocurrent can be enhanced by a factor of 5 relative to Zn-perylene MOF thin film due to triplet–triplet annihilation up-conversion between the Bodipy/PMMA sensitizer and the Zn-perylene MOF thin film acceptor using Co(bpy)32+/3+ as redox mediator.

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37

Zhang, Fengxia, Xianqiang Huang, Xiaofeng Wei, Huixue Ren, Tianyi Jiang, Xuemei Li, Junsen Wu i Yongshan Ma. "Synthesis and properties of bay unilaterally extended and mono-substituted perylene diimides". Journal of Chemical Research 44, nr 1-2 (14.11.2019): 60–66. http://dx.doi.org/10.1177/1747519819886502.

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The synthesis of two sulfur-decorated perylene diimides, the five-membered S-heterocyclic annulated perylene diimide (1) and 1-propanethiol- N,N′-dicyclohexylperylene-3,4,9,10-tetracarboxylic diimide (2), and a novel sulfoxide-containing perylene diimide, 1-propyl sulfoxide- N,N′-dicyclohexylperylene-3,4,9,10-tetracarboxylic diimide (3), are reported. The photophysical, electrochemical, aggregation, and thermal properties of these compounds are investigated by ultraviolet visible absorption, fluorescence, cyclic voltammetric, X-ray diffraction, and thermogravimetric analysis techniques. The geometries of the compounds are optimized at the 6-31G* level of theory using density functional theory, and their potentials are correlated with molecular orbitals. The prepared perylene diimide derivatives exhibit narrow the highest occupied molecular orbitals and the lowest unoccupied molecular orbitals band gaps, and they have quite different absorptions and emissions in dichloromethane solutions, which are in agreement with the density functional theory–calculated results.

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38

Mameri, Samir, Joanna R. Siekierzycka i Albert M. Brouwer. "Artificial miniaturized luminescent materials based on perylene-covered glass surfaces". New Journal of Chemistry 41, nr 14 (2017): 6083–88. http://dx.doi.org/10.1039/c7nj01337j.

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Cu(i)-Catalyzed 1,3-dipolar cycloaddition was used to construct a luminescent monolayer for an ICT-showing pyrrolidino-perylene association (5PMI) on glass surfaces, which represents a rare perylene chromophore, to date, anchored to a solid surface.

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39

Balashova, T. V., S. K. Polyakova, A. A. Fagin, V. A. Ilichev, K. A. Kozhanov, E. V. Baranov, G. K. Fukin i M. N. Bochkarev. "The First Perylene Complexes of Neodymium and Dysprosium". Координационная химия 49, nr 5 (1.05.2023): 259–68. http://dx.doi.org/10.31857/s0132344x22600291.

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Neodymium and dysprosium perylene complexes LnI(Per)(DME)2⋅Per (Ln = Nd, Dy) were obtained for the first time by the reaction of the Ln diiodides with perylene in dimethoxyethane. The structure of dysprosium complex was established by X-ray diffraction (CCDC no. 2184200). Experimental–theoretical electron density analysis was performed to specify the type of coordination between the dysprosium cation and perylene in DyI(Per)(DME)2⋅Per. Despite the identical composition, the Nd and Dy complexes have different structures, which is reflected in their luminescence properties.

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40

Voskoboynikov, Alexander, Bogdan Guzeev, Dmitry Mladentsev, Mikhail Sharikov, Georgy Goryunov i Dmitry Uborsky. "Synthesis of Perylene-Tagged Internal and External Electron Donors for Magnesium Dichloride Supported Ziegler–Natta Catalysts". Synthesis 51, nr 06 (6.11.2018): 1399–407. http://dx.doi.org/10.1055/s-0037-1611085.

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We report on the synthesis of three perylene-tagged electron donors representing three major types – phthalates, diethers, and alkoxysilanes – which are of importance for the subsequent studies of MgCl2-supported Ziegler–Natta catalysts by means of laser scanning confocal fluorescence microscopy. The obtained products were unambiguously characterized, including by X-ray crystal structure analysis; their photophysical properties (absorption and emission spectra) were investigated as well. Additionally, a reliable and convenient protocol for the multigram synthesis of the required starting material – 3-bromoperylene (PerBr) – was developed. The key step of this method was synthesis of trialkylsilyl-substituted perylenes, which were further separated by means of flash chromatography followed by conversion of the isolated 3-trialkylsilyl-substituted product to PerBr.

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41

Piryatinski, Yuri P., Markiian B. Malynovskyi, Maryna M. Sevryukova, Anatoli B. Verbitsky, Olga A. Kapush, Aleksey G. Rozhin i Petro M. Lutsyk. "Mixing of Excitons in Nanostructures Based on a Perylene Dye with CdTe Quantum Dots". Materials 16, nr 2 (6.01.2023): 552. http://dx.doi.org/10.3390/ma16020552.

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Semiconductor quantum dots of the A2B6 group and organic semiconductors have been widely studied and applied in optoelectronics. This study aims to combine CdTe quantum dots and perylene-based dye molecules into advanced nanostructure system targeting to improve their functional properties. In such systems, new electronic states, a mixture of Wannier–Mott excitons with charge-transfer excitons, have appeared at the interface of CdTe quantum dots and the perylene dye. The nature of such new states has been analyzed by absorption and photoluminescence spectroscopy with picosecond time resolution. Furthermore, aggregation of perylene dye on the CdTe has been elucidated, and contribution of Förster resonant energy transfer has been observed between aggregated forms of the dye and CdTe quantum dots in the hybrid CdTe-perylene nanostructures. The studied nanostructures have strongly quenched emission of quantum dots enabling potential application of such systems in dissociative sensing.

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42

Liang, Meng, Jun Yin, Kadali Chaitanya i Xue-Hai Ju. "Theoretical investigations on charge transfer properties of fluorinated perylene diimides". Journal of Theoretical and Computational Chemistry 15, nr 03 (maj 2016): 1650027. http://dx.doi.org/10.1142/s0219633616500279.

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The charge transport properties of perylene diimide (PDI) and its fluorinated derivatives were explored by density functional theory (DFT) coupled with the incoherent charge-hopping model. The geometric structure, reorganization energy, frontier molecule orbital, electron affinity (EA), ionization potential (IP), transfer integral as well as the anisotropic mobility were discussed. By attaching fluorine atoms to the bay region of PDI, the p-type material converts to the n-type or ambipolar ones (difluorinated-perylene diimide (DF-PDI) and tetraflurinated-perylene diimide (TF-PDI)). The electron mobility of difluorinated-perylene diimide (DF-PDI) (0.33[Formula: see text]cm2 V[Formula: see text] s[Formula: see text] is much larger than its corresponding hole mobility (0.0008[Formula: see text]cm2 V[Formula: see text] s[Formula: see text] due to its lower LUMO energy and more efficient pack-stacking, hence it could be a candidate of n-type organic semiconductor (OSC). The introduction of strong electron-withdrawing substituents (such as fluorine) to the perylene-based OSC materials is a promising strategy for the high-performance n-type OSCs. Besides, the three molecules exhibit remarkable anisotropic behaviors. Both the hole and electron maximal mobilities occur in the parallel [Formula: see text]–[Formula: see text] stacking dimers.

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43

Roa-Linares, Vicky C., Ana C. Mesa-Arango, Ramón J. Zaragozá i Miguel A. González-Cardenete. "Antifungal Activity of Amphiphilic Perylene Bisimides". Molecules 27, nr 20 (14.10.2022): 6890. http://dx.doi.org/10.3390/molecules27206890.

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Perylene-based compounds, either naturally occurring or synthetic, have shown interesting biological activities. In this study, we report on the broad-spectrum antifungal properties of two lead amphiphilic perylene bisimides, compounds 4 and 5, which were synthesized from perylene-3,4,9,10-tetracarboxylic dianhydride by condensation with spermine and an ammonium salt formation. The antifungal activity was evaluated using a collection of fungal strains and clinical isolates from patients with onychomycosis or sporotrichosis. Both molecules displayed an interesting antifungal profile with MIC values in the range of 2–25 μM, being as active as several reference drugs, even more potent in some particular strains. The ammonium trifluoroacetate salt 5 showed the highest activity with a MIC value of 2.1 μM for all tested Candida spp., two Cryptococcus spp., two Fusarium spp., and one Neoscytalidium spp. strain. Therefore, these amphiphilic molecules with the perylene moiety and cationic ammonium side chains represent important structural features for the development of novel antifungals.

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44

Wei, Hui Min, Nan Zhao, Nan Jiang, Wen Feng Duan i Bao Xiang Gao. "The Synthesis and Electro-Optical Properties of Perylene Dicarboximide Dimer with Electron Withdrawing Groups". Advanced Materials Research 936 (czerwiec 2014): 950–54. http://dx.doi.org/10.4028/www.scientific.net/amr.936.950.

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Perylene dicarboximide dimer with electron withdrawing groups were synthesized and fully characterized by 1H-NMR and 13C-NMR spectra. The effects of the substituted groups on the optical and electrochemical properties of the two compounds were investigated. The ∏-∏* absorption peak of the perylene dicarboximide dimer compounds were red shifted from 525nm to 535nm. The band gaps of the dimer could be tuned from 2.28 eV to 2.13 eV. The first reduction wave of the dimer with electron withdrawing groups is shifted by 60 mV to more positive potential compared to that of perylene dicarboximide, suggesting the enhanced electron affinity. Furthemore, the dimer exhibited intermolecular aggregation, and decrease fluorescence quantum yield.

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45

Datars, W. R., T. R. Chien i P. K. Ummat. "Properties of perylene reacted with AsF5". Canadian Journal of Physics 73, nr 11-12 (1.11.1995): 653–57. http://dx.doi.org/10.1139/p95-097.

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Perylene (Per) was reacted with AsF5 dissolved in liquid SO2 to produce Per(AsF6)2. Far infrared absorption showed absorption by AsF6−. Nuclear magnetic resonance of 19F consisted of a quartet formed by indirect nuclear–nuclear coupling. The change of mass through the reaction indicated the formula Per(AsF6)2. Mass spectroscopy showed bonding between perylene and F and indicated no SO2 solvent in the sample. This solvent-free material does not conduct electrically. X-ray diffraction showed that the structure has an orthorhombic cell. Exposure to air changes the sample weight and colour, and results in conduction with semiconducting properties and reduced bonding between AsF6− and perylene.

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46

Salzillo, Tommaso, Raffaele G. Della Valle, Elisabetta Venuti, Aldo Brillante, Gabriele Kociok-Köhn, Daniele Di Nuzzo, Matteo Masino i Alberto Girlando. "(Perylene)3-(TCNQF1)2: Yet Another Member in the Series of Perylene–TCNQFx Polymorphic Charge Transfer Crystals". Crystals 10, nr 3 (6.03.2020): 177. http://dx.doi.org/10.3390/cryst10030177.

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The 3:2 Charge Transfer (CT) co-crystal (Perylene)3(TCNQF1)2 is grown by the Physical Vapor Transport (PVT) method, and characterized structurally and spectroscopically. Infrared analysis of the charge sensitive modes reveals a low degree of charge transfer (less than 0.1) between donor and acceptor molecules. The crystal is isostructural to the other 3:2 CT crystals formed by Perylene with TCNQF2 and TCNQF4, whereas such stoichiometry and packing is not known for the CT crystals with non-fluorinated TCNQ. The analysis of the isostructural family of 3:2 Perylene–TCNQFx (x = 1,2,4) co-crystal put in evidence the role of weak F…HC bonding in stabilizing this type of structure

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47

Fujimoto, Keisuke, Masaki Takahashi, Seiichiro Izawa i Masahiro Hiramoto. "Development of Perylene-Based Non-Fullerene Acceptors through Bay-Functionalization Strategy". Materials 13, nr 9 (6.05.2020): 2148. http://dx.doi.org/10.3390/ma13092148.

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Perylene has had a tremendous impact in the history of material research for the molecular semiconductors. Among numerous derivatives of this polyaromatic hydrocarbon, perylene diimide (PDI) represents a promising class of organic materials envisioned as non-fullerene acceptors (NFAs) for the practical organic photovoltaic (OPV) applications due to their enhanced photo- and thermal stability and remarkably high electron affinity, some of which realize band-like transport properties. The present review guides some of the representative achievements in the development of rationally designed PDI systems, highlighting synthetic methodologies based on bay-functionalization strategies for creating well-designed molecular nanostructures and structure-performance relationship of perylene-based small molecular acceptors (SMAs) for the photovoltaic outcomes.

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Alves, Alessandro L., Simone V. Bernardino, Carlos H. Stadtlober, Edivandro Girotto, Giliandro Farias, Rodney M. do Nascimento, Sergio F. Curcio i in. "Charge carrier transport in perylene-based and pyrene-based columnar liquid crystals". Beilstein Journal of Organic Chemistry 19 (16.11.2023): 1755–65. http://dx.doi.org/10.3762/bjoc.19.128.

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Electron and hole transport characteristics were evaluated for perylene-based and pyrene-based compounds using electron-only and hole-only devices. The perylene presented a columnar hexagonal liquid crystal phase at room temperature with strong molecular π-stacking inside the columns. The pyrene crystallizes bellow 166 °C, preserving the close-packed columnar rectangular structure of the mesophase. Photophysical analysis and numerical calculations assisted the interpretation of positive and negative charge carrier mobilities obtained from fitting the space charge limited regime of current vs voltage curves. The pyrene-based material demonstrated an electron mobility two orders of magnitude higher than the perylene one, indicating the potential of this class of materials as electron transporting layer.

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Takahashi, Masaki, Yousuke Suzuki, Yasunori Ichihashi, Mitsuji Yamashita i Hideki Kawai. "1,3,8,10-Tetrahydro-2,9-diazadibenzo[cd,lm]perylenes: synthesis of reduced perylene bisimide analogues". Tetrahedron Letters 48, nr 3 (styczeń 2007): 357–59. http://dx.doi.org/10.1016/j.tetlet.2006.11.100.

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50

Hu, Xiao Jun, Xin Yan Hu i Zhi Zhang. "A New Approach to Fluorescent Chemosensor of Cu²⁺ Ion". Applied Mechanics and Materials 513-517 (luty 2014): 65–69. http://dx.doi.org/10.4028/www.scientific.net/amm.513-517.65.

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According to the principle of dynamic quenching a new ON-OFF fluorescent chemosensor for Cu2+ions was designed, this chemosensor was composed of p-tert-butylthiacalix [arene (TCA),sodium dodecyl sulfate (SDS) and perylene through the form of self-assembly in aqueous solution. Addition of Cu2+ions could result in a quenching of the fluorescence emission of perylene inside micelles, which due to intramicellar complex-fluorophore electron-transfer or energy-transfer effects induced by the complexation of TCA with the Cu2+ions.The experimental results indicated that: Under the condition of TCA/perylene was 800/1, SDS concentration was 150mmol/L and pH value above 9, according to the fluorescence quenching ,within a certain range of the concentration of Cu2+ion can be linearly determined.

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