156028-26-1Relevant articles and documents
1D Self-Assembly and Ice Recrystallization Inhibition Activity of Antifreeze Glycopeptide-Functionalized Perylene Bisimides
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.
, p. 7834 - 7839 (2018)
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.
Supramolecular assembly of fluorogenic glyco-dots from perylenediimide-based glycoclusters for targeted imaging of cancer cells
Liu, Ying,Ji, Ding-Kun,Dong, Lei,Galanos, Nicolas,Zang, Yi,Li, Jia,Vidal, Sébastien,He, Xiao-Peng
, p. 11937 - 11940 (2017)
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.
Influence of chlorine atoms in bay positions of perylene-tetracarboxylic acids on their spectral properties in Langmuir-Blodgett films
Piosik, Emilia,Synak, Anna,Martyński, Tomasz
, p. 374 - 380 (2018)
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.
Increasing 3D supramolecular order by decreasing molecular order. A comparative study of helical assemblies of dendronized nonchlorinated and tetrachlorinated perylene bisimides
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
, p. 5210 - 5224 (2015)
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.
Efficient electron transporting and panchromatic absorbing FRET cassettes based on aza-BODIPY and perylenediimide towards multiple metal FRET-Off sensing and ratiometric temperature sensing
Rani, Kavita,Pandey, Upendra K.,Sengupta, Sanchita
supporting information, p. 4607 - 4618 (2021/04/13)
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.
Colored composition, and a color filter comprising a color conversion
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Paragraph 0024; 0064; 0068, (2021/10/08)
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
COLORED COMPOSITION, COLOR CONVERSION OPTICAL FILTER COMPRISING THE COLORED COMPOSITION, AND DISPLAY DEVICE
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Paragraph 0097-0099, (2021/01/08)
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.
The synthesis and characterisation of the perylene acid dye inks for digital textile printing
Choi, Sol,Cho, Kwan Hyun,Namgoong, Jin Woong,Kim, Jeong Yun,Yoo, Eui Sang,Lee, Woosung,Jung, Jae Woong,Choi, Jun
, p. 381 - 392 (2019/01/03)
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.
Perylenetetracarboxy-3,4:9,10-diimide derivatives with large two-photon absorption activity
Garoni, Eleonora,Nisic, Filippo,Colombo, Alessia,Fantacci, Simona,Griffini, Gianmarco,Kamada, Kenji,Roberto, Dominique,Dragonetti, Claudia
, p. 1885 - 1893 (2019/01/26)
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.
Fluorofluorescent Perylene Bisimides
Yoshinaga, Kosuke,Swager, Timothy M.
, p. 2509 - 2514 (2018/11/30)
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.
