- 1D Self-Assembly and Ice Recrystallization Inhibition Activity of Antifreeze Glycopeptide-Functionalized Perylene Bisimides
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Antifreeze glycoproteins (AFGPs) are polymeric natural products that have drawn considerable interest in diverse research fields owing to their potent ice recrystallization inhibition (IRI) activity. Self-assembled materials have emerged as a promising class of biomimetic ice growth inhibitor, yet the development of AFGP-based supramolecular materials that emulate the aggregative behavior of AFGPs have not yet been reported. This work reports the first example of the 1D self-assembly and IRI activity of AFGP-functionalized perylene bisimides (AFGP-PBIs). Glycopeptide-functionalized PBIs underwent 1D self-assembly in water and showed modest IRI activity, which could be tuned through substitution of the PBI core. This work presents essential proof-of-principle for the development of novel IRIs as potential supramolecular cryoprotectants and glycoprotein mimics.
- Adam, Madeleine K.,Jarrett-Wilkins, Charles,Beards, Michael,Staykov, Emiliyan,MacFarlane, Liam R.,Bell, Toby D. M.,Matthews, Jacqueline M.,Manners, Ian,Faul, Charl F. J.,Moens, Pierre D. J.,Ben, Robert N.,Wilkinson, Brendan L.
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- Supramolecular assembly of fluorogenic glyco-dots from perylenediimide-based glycoclusters for targeted imaging of cancer cells
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Supramolecular self-assembly between perylenediimide-based glycoclusters and a red-emitting fluorophore produces structurally uniform and stable glyco-dots amenable to targeted fluorogenic imaging of liver and triple-negative breast cancer cells.
- Liu, Ying,Ji, Ding-Kun,Dong, Lei,Galanos, Nicolas,Zang, Yi,Li, Jia,Vidal, Sébastien,He, Xiao-Peng
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- Influence of chlorine atoms in bay positions of perylene-tetracarboxylic acids on their spectral properties in Langmuir-Blodgett films
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The influence of chlorine atoms in the bay positions of the perylene-3,4,9,10-tetracarboxylic acids with the different alkyl chains length on their spectral properties in monomolecular films has been studied. The chlorinated (PCln) and for comparison non-chlorinated (Pn) perylene derivatives were deposited onto quartz plates using a Langmuir-Blodgett (LB) technique. The absorption spectra showed that the PCln and Pn dyes form in monolayers the I- and J-type aggregates, respectively. In turn, their steady-state and time-resolved emission spectra revealed presence of two emitter types, which we assigned to monomers and excimers. The luminescence lifetimes of the PCln monomers and excimers determined with a time-correlated single photon counting method (TCSPC) are significantly shorter than these obtained for the same emitter types in the Pn monolayers. In the case of the chlorinated dyes, the contribution of the monomer emission dominates over the excimer emission and is almost independent from the alkyl chain length. By contrast, the share of the Pn monomer emission increases strongly with a number of carbon atoms in their hydrocarbon chains. The luminescence quantum yields (LQY) of the Pn and PCln monolayers measured in an integrating sphere are in the range of 0.06–0.11. The presented results reveal that the PCln dyes exhibit lower tendency for aggregation than the non-chlorinated derivatives. It can be explained by limited intermolecular interaction between neighbouring PCln molecules caused by deformation of the perylene core as a result of strongly electronegative chlorine atoms in the bay positions of these dyes. Moreover, the strong influence of the alkyl chain length on the Pn aggregation contrary to the case of the PCln derivatives was observed.
- Piosik, Emilia,Synak, Anna,Martyński, Tomasz
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- Increasing 3D supramolecular order by decreasing molecular order. A comparative study of helical assemblies of dendronized nonchlorinated and tetrachlorinated perylene bisimides
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A nonplanar, twisted, and flexible tetrachlorinated perylene bisimide (Cl4PBI) was functionalized with two AB3 minidendrons containing hydrogenated or semifluorinated dodecyl groups. The hydrogenated dendron was attached to the imide groups of Cl4PBI via m = 0, 1, and 2 methylenic units, whereas the dendron containing semifluorinated groups was attached via m = 3 or a di(ethylene oxide) linker (m = 2EO). The supramolecular structures of these compounds, determined by a combination of differential scanning calorimetry, X-ray diffraction, and solid-state NMR, were compared with those of nonchlorinated planar and rigid PBI reported previously, which demonstrated the thermodynamically controlled formation of 2D periodic arrays at high temperatures and 3D arrays at low temperatures. The molecularly less ordered Cl4PBI containing hydrogenated dendrons self-organize into exclusively 3D crystalline periodic arrays under thermodynamic control for m = 0 and 2, while the more highly molecularly ordered PBI produced less stable and ordered 3D crystals and also 2D assemblies. This induction of a higher degree of 3D order in supramolecular assemblies of the less well-ordered molecular building blocks was unanticipated. The semifluorinated dendronized Cl4PBI with m = 3 formed a 2D columnar hexagonal array under kinetic control, whereas the compound with m = 2EO formed an unusual 2D honeycomb-like hexagonal phase under thermodynamic control. These Cl4PBI compounds provide a new route to stable crystalline assemblies via thermodynamic control at lower temperatures than previously obtained with PBI, thus generating 3D order in an accessible range of temperature of interest for structural analysis and for technological applications.
- Partridge, Benjamin E.,Leowanawat, Pawaret,Aqad, Emad,Imam, Mohammad R.,Sun, Hao-Jan,Peterca, Mihai,Heiney, Paul A.,Graf, Robert,Spiess, Hans W.,Zeng, Xiangbing,Ungar, Goran,Percec, Virgil
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- Efficient electron transporting and panchromatic absorbing FRET cassettes based on aza-BODIPY and perylenediimide towards multiple metal FRET-Off sensing and ratiometric temperature sensing
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Multichromophoric triads 1 and 2 based on aza-BODIPY as the central chromophore and bay-substituted (tetrachloro- and tetraphenoxy-)perylenediimides (PDI) as peripheral chromophores have been designed and synthesized that are panchromatic absorbers and near infrared (NIR) emitters. Both triads 1 and 2 exhibited ~99% F?rster resonance energy transfer (FRET) from the peripheral PDIs to central aza-BODIPY. The excitation energy transfer from PDI to aza-BODIPY was studied via steady state emission, fluorescence quantum yield, time resolved fluorescence emission and theoretical calculations. These studies revealed quantitative singlet excitation energy transfer efficiencies for 1 and 2. Electrochemical studies revealed the strong electron deficient character of these triads and thus electron mobilities of these triads were measured using space charge limited current (SCLC) method. Triads 1 and 2 exhibited appreciable electron mobilities of 2.44 ± 1.70 × 10-3 cm2 V-1 s-1 and 4.00 ± 1.50 × 10-3 cm2 V-1 s-1 respectively, an order of magnitude higher mobility than aza-BODIPY based small molecules reported in the literature. Leveraging upon the dual emission behaviour of these triads, ratiometric FRET sensing as well as ratiometric temperature sensing behaviour were investigated via steady state absorption and fluorescence measurements. Triads 1 and 2 showed remarkable ratiometric FRET-off sensing where the addition of metals such as Co2+ and Fe3+ led to near-quantitative FRET off for both the triads. Triads 1 and 2 also serve as efficient ratiometric temperature sensors with positive temperature coefficients and small temperature sensitivities of ~0.29% °C-1 and ~0.14% °C-1 respectively that suggest the possibility of precise physiological temperature measurements using these triads.
- Rani, Kavita,Pandey, Upendra K.,Sengupta, Sanchita
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supporting information
p. 4607 - 4618
(2021/04/13)
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- Colored composition, and a color filter comprising a color conversion
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The white light source is used for the color conversion filter [to] the display colored composition, certain specific wavelength conversion can efficiently absorb light of the backlight, and, even if the coloring composition can improve the color reproducibility of a display. A liquid crystal display or an organic EL display using an optical filter for color-converting colorant [a] the composition, the following formula (1)(In formula (1), the amino sulfonyl phenyl group which may have substituent A, the phenyl group may have substituent B. ) A coloring composition containing a binder resin and a perylene compound represented. [Drawing] no
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Paragraph 0024; 0064; 0068
(2021/10/08)
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- COLORED COMPOSITION, COLOR CONVERSION OPTICAL FILTER COMPRISING THE COLORED COMPOSITION, AND DISPLAY DEVICE
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Embodiments of the present invention are described below. Provided is a coloring composition for a color conversion optical filter used in a display including white light as a light source, capable of efficiently converting a specific wavelength into a specific wavelength to which a specific backlight light is absorbed, and improving color reproducibility of the display. To solve this problem, the present invention provides the following. Coloring composition for color conversion optical filters used in liquid crystal displays or organic EL displays, wherein the following formula (1) is used. (In the formula (1), A represents the following formulae (1-A) and B: (1-B). In the formula (1-A), R represents a hydrogen atom. 1 To R5 Each independently represents a hydrogen atom or an alkyl group 1 having 10 carbon atoms. In formula (1-B), R represents a hydrogen atom. 6 To R10 Each independently represents a hydrogen atom, a halogen atom, an alkyl group having 1 or 10 carbon atoms, or a methoxy group. However, this is not limited thereto. R6 To R10 A coloring composition, comprising: a perylene compound represented by a substituent represented by a substituent represented by the following general formula; and a binder resin.
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Paragraph 0097-0099
(2021/01/08)
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- The synthesis and characterisation of the perylene acid dye inks for digital textile printing
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Five perylene acid dyes were synthesized to manufacture water-based inks for the high-speed ink jet printing process, including digital textile printing. All the synthesized perylene dyes exhibited superior stability and optical properties compared to a commercially used azo dye. Their water solubility was efficiently enhanced by introducing bulky and hydrophilic substituents to ensure excellent long-term stability when formulated as water-based inks. The water-based inks with these perylene dyes showed outstanding print clarity with the colours different from the basic colour composition of the existing digital textile printing inks. They also exhibited good ejection performance and helped conduct well-controlled pattern printing when used in a commercial ink jet printing machine.
- Choi, Sol,Cho, Kwan Hyun,Namgoong, Jin Woong,Kim, Jeong Yun,Yoo, Eui Sang,Lee, Woosung,Jung, Jae Woong,Choi, Jun
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p. 381 - 392
(2019/01/03)
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- Perylenetetracarboxy-3,4:9,10-diimide derivatives with large two-photon absorption activity
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Three new perylenetetracarboxy-3,4:9,10-diimides, bearing 2,6-diisopropylphenyl groups at the imide positions and 4-(R-ethynyl)phenoxy moieties (R = 4,7-di(2-thienyl)benzo[c][1,2,5]thiadiazole (P2), pyrene (P3) or pyrene-CH2OCH2 (P4)) at the four bay positions, were prepared, along with the known related derivative (R = phenyl (P1)), and well characterized. They have large two-photon absorption (TPA) cross-sections (σ2), as determined by the Z-scan technique, the highest values being reached with P2 which bears a planar π-delocalized donor moiety. P3 is characterized by higher σ2 values than both P1, as expected for the higher π-conjugation of the donor pyrene moiety with respect to phenyl, and P4, due to the presence of the flexible and non-conjugated CH2OCH2 bridge between the pyrene and the ethynyl fragment in the latter compound. The molecular geometry of P1-P4 has been optimized by DFT modeling, showing that in P2 and P3 the bay substituents are stacked due to the π-π interactions of both pyrene and thiophene groups. The LUMO of P1-P4 lies at the same energy and is essentially delocalized on the perylene core whereas the HOMO and HOMO?1 of both P2 and P3 are degenerate and do not show contribution from the perylene core contrarily to that of P1 and P4. The HOMO-LUMO gap is therefore essentially influenced by the HOMO which reflects the electronic charge delocalization on the bay substituents, the lower gaps being observed for P2 and P3, which are characterized by the best TPA properties.
- Garoni, Eleonora,Nisic, Filippo,Colombo, Alessia,Fantacci, Simona,Griffini, Gianmarco,Kamada, Kenji,Roberto, Dominique,Dragonetti, Claudia
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p. 1885 - 1893
(2019/01/26)
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- Fluorofluorescent Perylene Bisimides
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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 Bronsted acids as well as aggregation in the fluorous phase.
- Yoshinaga, Kosuke,Swager, Timothy M.
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p. 2509 - 2514
(2018/11/30)
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- Synthesis and characterization of fluorescent dyes and their applications for the enhancement of growth rate of Chlorella vulgaris
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Spectral conversion of solar radiation from green to red light can enhance the photosynthesis efficiency of microalgae. This can lead to significant increase in microalgal growth. Four perylene-based fluorescent dyes were synthesized to convert wavelengths of light from green (500–570 nm) to orange-red (580–650 nm). These dyes were applied in microalgal cultivation system using two methodologies: (1) light-converting layer, and (2) light-converting medium. The dyes were dissolved in either ethanol or water to form light-converting layers between microalgae culture and the light source. Under converted light in both set-ups, Chlorella vulgaris cultures showed maximum increase in lipid productivity by 13.00% and 17.15%, and biomass productivity by 31.65% and 37.66% compared to the control. Overall, the cultivation results confirmed beneficial effects of modified light on microalgae cultures both on their lipid and biomass productivities. Note that both growth parameters achieved higher performance in the light-converting medium thereby the effectiveness of the cultivation method was validated.
- Jang, Hyeyoun,Namgoong, Jin Woong,Sung, Min-Gyu,Chang, Yongkeun,Kim, Jae Pil
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p. 142 - 150
(2018/05/28)
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- Perylenediimide-based glycoclusters as high affinity ligands of bacterial lectins: Synthesis, binding studies and anti-adhesive properties
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The synthesis of eight perylenediimide-based glycoclusters was readily performed from hexa- and tetra-propargylated cores through azide-alkyne "click" conjugation. Variations in the carbohydrate epitope (Glc, Gal, Man, Fuc) and the linker arm provided molecular diversity. Interactions with LecA and LecB, two proteins involved in the adhesion of Pseudomonas aeruginosa to host tissues, were evaluated by microcalorimetry (ITC). In both cases high affinities were obtained with Kd values in the nanomolar range. Further evaluation of their anti-adhesive properties using cultured epithelial cells demonstrated their potent anti-adhesive activities against Pseudomonas aeruginosa with only 30-40% residual adhesion observed. The fluorescence properties of the PDI core were then investigated by confocal microscopy on cell-bacteria cultures. However, the red fluorescence signal of the PDI-based glycocluster was too weak to provide significant data. The present study provides another type of anti-adhesive glycocluster against bacterial infection with a large aromatic PDI core.
- Donnier-Maréchal, Marion,Galanos, Nicolas,Grandjean, Teddy,Pascal, Yoann,Ji, Ding-Kun,Dong, Lei,Gillon, Emilie,He, Xiao-Peng,Imberty, Anne,Kipnis, Eric,Dessein, Rodrigue,Vidal, Sébastien
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supporting information
p. 10037 - 10043
(2017/12/26)
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- COMPOSITION INCLUDING MIXTURE OF RYLENE-BASED COMPOUND DERIVATIVES, USES OF THE SAME, AND PREPARING METHOD OF THE SAME
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The present invention relates to a composition comprising a mixture of derivatives of a rylene-based compound, a use of the composition comprising a mixture of derivatives of a rylene-based compound, and to a preparation method of the composition comprising a mixture of derivatives of a rylene-based compound. The derivatives of a rylene-based compound are represented by chemical formulas 1 and 2. The composition can be used as an electronic material, a light-emitting color filter, and a semi-transparent color filter, and a coloring component or a color-correcting component of a reflective device.
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Paragraph 0169-0171
(2017/06/09)
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- Screening Libraries of Semifluorinated Arylene Bisimides to Discover and Predict Thermodynamically Controlled Helical Crystallization
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Synthesis, structural, and retrostructural analysis of a library containing 16 self-assembling perylene (PBI), 1,6,7,12-tetrachloroperylene (Cl4PBI), naphthalene (NBI), and pyromellitic (PMBI) bisimides functionalized with environmentally friendly AB3 chiral racemic semifluorinated minidendrons at their imide groups via m = 0, 1, 2, and 3 methylene units is reported. These semifluorinated compounds melt at lower temperatures than homologous hydrogenated compounds, permitting screening of all their thermotropic phases via structural analysis to discover thermodynamically controlled helical crystallization from propeller-like, cogwheel, and tilted molecules as well as lamellar-like structures. Thermodynamically controlled helical crystallization was discovered for propeller-like PBI, Cl4PBI and NBI with m = 0. Unexpectedly, assemblies of twisted Cl4PBIs exhibit higher order than those of planar PBIs. PBI with m = 1, 2, and 3 form a thermodynamically controlled columnar hexagonal 2D lattice of tilted helical columns with intracolumnar order. PBI and Cl4PBI with m = 1 crystallize via a recently discovered helical cogwheel mechanism, while NBI and PMBI with m = 1 form tilted helical columns. PBI, NBI and PMBI with m = 2 generate lamellar-like structures. 3D and 2D assemblies of PBI with m = 1, 2, and 3, NBI with m = 1 and PMBI with m = 2 exhibit 3.4 ? π-π stacking. The library approach applied here and in previous work enabled the discovery of six assemblies which self-organize via thermodynamic control into 3D and 2D periodic arrays, and provides molecular principles to predict the supramolecular structure of electronically active components.
- Ho, Ming-Shou,Partridge, Benjamin E.,Sun, Hao-Jan,Sahoo, Dipankar,Leowanawat, Pawaret,Peterca, Mihai,Graf, Robert,Spiess, Hans W.,Zeng, Xiangbing,Ungar, Goran,Heiney, Paul A.,Hsu, Chain-Shu,Percec, Virgil
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supporting information
p. 723 - 739
(2016/12/22)
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- COMPOUND, SOLAR CELL MODULE, AND PHOTOVOLTAIC POWER GENERATION DEVICE
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This compound is represented by the following general formula (IA) or (IB) (in the formula, R1 and R2 are each independently a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, or an aryloxy group, and a plurality of the R1 and the R2 may be the same as each other or different from each other; R3 corresponds to a hydrogen atom or an alkyl group, and a plurality of R3 may be the same as each other or different from each other). A solar cell module includes the compound. A photovoltaic power generation device includes the solar cell module.
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Paragraph 0253; 0254; 0255; 0256; 0257
(2016/01/30)
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- Compound, solar cell module, and solar power generation device
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A compound is represented by the following general formula (IA0) or (IB0). A solar cell module for which the compound is used is used for a solar power generation device.
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Page/Page column 67; 68; 69; 70; 71; 72
(2016/06/06)
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- Antioxidants Having Aromatic Structures Reacting with Superoxide
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Disclosed is a method of treating diseases which are: reactive oxygen species mediated, ischemic or reperfusion-related, or T-cell mediated, including autoimmune diseases. The method is administering a therapeutically effective amount of a formulation wherein the active ingredient includes non-phenolic aromatic structures that are electron deficient and are capable of converting the superoxide radical to O2; and/or of converting superoxide radical to oxygen and hydrogen peroxide, or pharmaceutically acceptable salts of said structures. Also disclosed is a method of diagnosing and treating such diseases and conditions.
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- Facile synthesis of pure 1,6,7,12-tetrachloroperylene-3,4,9,10-tetracarboxy bisanhydride and bisimide
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A robust and scalable procedure to obtain pure 1,6,7,12-tetrachloroperylene-3,4,9,10-tetracarboxy bisanhydride, a highly valuable synthon, has been developed via synthesis of a novel intermediate compound 1,6,7,12-perylene-3,4,9,10-tetracarboxy tetrabutylester.
- Dubey, Rajeev K.,Westerveld, Nick,Grozema, Ferdinand C.,Sudh?lter, Ernst J. R.,Jager, Wolter F.
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supporting information
p. 1882 - 1885
(2015/04/27)
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- Synthesis of hyperbranched polythiophenes containing tetrachloroperylene bisimide as bridging moiety for polymer solar cells
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The goal of this research is to synthesize the hyperbranched polythiophene derivatives (P1 and P4) containing tetrachloroperylene bisimide as bridging moiety for investigation of thermal, electrochemical, and opto-electrical properties of these derivatives. The polymers (P2 and P3) containing soft alkyl spacer as bridging moiety and linear poly(3-hexylthiophene) (P3HT) were also synthesized for comparison in this study. Polymers with high regioregularity were synthesized via the Universal Grignard metathesis polymerization. The GPC results showed that molecular weights of hyperbranched polythiophenes are higher than that of P3HT. The TGA experiments revealed a first-stage weight loss at about 300 °C for all polymers; besides, polymers containing rigid tetrachloroperylene bisimide groups possess less weight loss than P3HT after heating, indicative of enhanced thermal stabilities. The UV-vis absorption maxima of hyperbranched polymers are similar to that of P3HT in film state, while their absorption shoulder bands are stronger than that of P3HT, indicating stronger interchain interaction and shorter distance between backbones by the introduction of bridge architecture. Moreover, an attenuation of fluorescent intensity was found for those hyperbranched polymers, implying reduced recombination of excitons to emit light and more opportunity for carriers to migrate to both electrodes. Electrochemical analysis showed that introducing hyperbranched structure resulted in decreasing both LUMO and HOMO levels of polymers. All polymers were used for fabrication of polymer solar cells with the configuration of ITO/PEDOT/polymer:PC60BM (1:2 w/w)/LiF/Al to evaluate their performance. The power conversion efficiency (PCE) of the P3HT:PC60BM-based device is 0.54%, while devices based on hyperbranched polymers showed PCE values in the range of 0.45-0.84%. The morphological study of polymer:PC60BM blend films was performed by AFM for interpretation of efficiency trend of devices.
- Yang, Sheng-Hsiung,Lin, Tz-Shiuan,Huang, Yu-Zhang,Li, Husan-De,Chao, Yu-Chiang
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p. 6058 - 6068
(2015/01/08)
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- Light harvesting and amplification of emission of donor perylene-acceptor perylene aggregates in aqueous medium
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With the aid of rational design, we have synthesized a pair of water-soluble donor- and acceptor-type twisted perylene bisimide units, which together form aggregates upon lowering the pH of the medium, providing bright yellow fluorescence. The light-harvesting efficiency of the co-assembled system can be tuned by controlling the ratio of donor to acceptor and 98.1 % efficiency has been achieved. Light harvesting: Through the use of rational design, a pair of water-soluble donor- and acceptor-type twisted perylene bisimide units have been synthesized. Together, these form aggregates when the pH of the medium is lowered, emitting bright yellow fluorescence. The light-harvesting efficiency of the co-assembled system can be tuned by controlling the ratio of donor to acceptor and over 98 % efficiency has been achieved.
- Sukul, Pradip K.,Datta, Ayan,Malik, Sudip
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supporting information
p. 3019 - 3022
(2014/03/21)
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- Hydrogen-bonded perylene/terthiophene-materials: Synthesis and spectroscopic properties
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The synthesis of layered donor/acceptor-materials based on perylenes (1a-c) and ter(thiophen)es (2a, 2b), ordered by hydrogen bonding moieties is reported. Based on the successful (selective) chlorination of 3,4:9,10-perylene tetracarboxylic dianhydride (3) to obtain a perylene derivative with only four chlorine atoms, subsequent functionalization with different hydrogen-bonding moieties is achieved via the azide/alkyne click reaction as proven by extensive ESI-TOF measurements. The perylene- (1a-c) and terthiophene- (2a, 2b) compounds are useful as acceptor and donor parts, respectively, in organic solar cells as proven via UV-vis and fluorescence measurements. Charge transfer between donor and acceptor parts (2a/1b) was determined as 41% via fluorescence resonance energy transfer (FRET), proving the association of the two components via the attached hydrogen bonding moieties. These measurements indicate that the mixture 2a/1b displays large potential for use as a layered ordered material with controlled spacings for organic solar cells based on a thereby facilitated charge-transfer.
- Shaygan Nia, Ali,Enders, Claudia,Binder, Wolfgang H.
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supporting information; scheme or table
p. 722 - 729
(2012/02/15)
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- Synthesis of perylene-bridged bis(dibenzo-24-crown-8) and its assembly behavior with a fullerene-based secondary dibenzylammonium salt
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This paper reports the synthesis of a perylene-bridged bis(crown ether) through the condensation reaction between primary amine-armed dibenzo-24-crown-8 and 3,4,9,10-perylenetetracarboxylic dianhydride. Pseudorotaxane with a perylene moiety at the wheel and a fullerene unit in the middle of the axle was prepared, which was evidenced by 1H NMR and fluorescence experiments. Subsequent investigations show that the formation and disassociation of the pseudorotaxane can be controlled by the alternating addition of KPF6 and 18-crown-6, following the change of the florescence intensity of perylene.
- Yao, Haiqing,Zhang, Hengyi,Han, Min,Ding, Zhijun,Zhang, Zhijun,Liu, Yu
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scheme or table
p. 1982 - 1986
(2011/02/21)
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- Synthesis and characterization of 1,7-disubstituted and 1,6,7,12-tetrasubstituted perylenetetracarboxy-3,4:9,10-diimide derivatives
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A variety of perylenetetracarboxy-3,4:9,10-diimide derivatives have been synthesized. Particular attention was paid to substituents in positions 1, 6, 7 or 12. The energy differences between the frontier orbitals have been determined using optical spectroscopy (UV and fluorescence). The energy of the lowest unoccupied orbitals (LUMOs) were obtained by cyclic voltammetry. From both studies, the energies of the highest occupied orbitals (HOMOs) were also been calculated. A Hammett-type relationship was observed for the reduction potentials (Ered11/2) when correlated with the σ-ortho parameter. The energies of the frontier orbitals define the domains of application of these compounds. They significantly depend on the substitution in positions 1, 6, 7, or 12.
- Queste, Mathieu,Cadiou, Cyril,Pagoaga, Bernard,Giraudet, Louis,Hoffmann, Norbert
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experimental part
p. 2537 - 2545
(2011/01/12)
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- Twisted perylene stereodimers reveal chiral molecular assembly codes
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Unique perylene diastereomeric linear and cyclic dimers were synthesized from twisted perylene monomers, revealing that π-stacking stereoisomerism imparted specific intermolecular self-assembly and intramolecular folding. Only the homochiral twisted tetrachloroperylene monomers cyclized via a cooperative reaction, forming the homochiral diastereomers. The heterochiral tetrachloroperylene monomers proceeded through a stepwise reaction and yielded a linear heterochiral dimer, which equilibrated with the linear homochiral dimers. The linear homochiral dimers cyclized to produce the same cyclic homochiral diastereomers. These results demonstrated that homochiral and heterochiral self-assemblies were two distinct molecular codes, directing two specific chemical pathways. The homochiral cyclic dimers remain isomerically pure at -20°C but can be interconverted to the heterochiral cyclic dimer meso compound at room temperature. The diastereomers were readily separated by HPLC. While driven by solvophobic forces, foldable linear dimers synthesized from the same twisted monomers using phosphoramidite chemistry folded into homodimer and heterodimer, confirming the inherent molecular codes, which were dictated by the perylene chirality, ultimately gauged the weak π-stack forces, and directed self-assembly and folding.
- Wang, Wei,Shaller, Andrew D.,Li, Alexander D. Q.
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scheme or table
p. 8271 - 8279
(2009/02/02)
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- Tunable molecular assembly codes direct reaction pathways
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In the twist: The extent of twisting from planarity in a series of perylenetetracarboxylic diimides (PDIs) modulates the attractive π-π stacking force, revealing an array of inherent molecular recognition codes. Such coded self-assembly directs specific reaction pathways so that a mixture of reactive monomers with different codes results in identical products as when the reactions were carried out in separate flasks (see picture).
- Shaller, Andrew D.,Wang, Wei,Gan, Haiyang,Li, Alexander D. Q.
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supporting information; experimental part
p. 7705 - 7709
(2009/04/11)
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- Fluorescent perylene diimide rotaxanes: Spectroscopic signatures of wheel-chromophore interactions
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[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.
- Baggerman, Jacob,Jagesar, Dhiredj C.,Vallee, Renaud A. L.,Hofkens, Johan,De Schryver, Frans C.,Schelhase, Franke,Voegtle, Fritz,Brouwer, Albert M.
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p. 1291 - 1299
(2007/10/03)
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