110590-84-6Relevant articles and documents
Restricted diffusion of guest molecules in polymer thin films on solid substrates as revealed by three-dimensional single-molecule tracking
Ito, Syoji,Taga, Yuhei,Hiratsuka, Kengo,Takei, Satoshi,Kitagawa, Daichi,Kobatake, Seiya,Miyasaka, Hiroshi
, p. 13756 - 13759 (2015)
3D single-molecule tracking revealed that the translational diffusion of guest dyes in poly(2-hydroxyethyl acrylate) thin films on glass substrates was confined in a horizontal layer at a distance longer than 300-700 nm from the surface of the substrate. This peculiar long-range effect suggests that the interaction between the host polymer and the interface could affect the properties of polymers at a much longer distance than conventionally estimated.
Original Suzuki–Miyaura Coupling Using Nitro Derivatives for the Synthesis of Perylenediimide-Based Multimers
Rocard, Lou,Hatych, Danylo,Chartier, Thomas,Cauchy, Thomas,Hudhomme, Piétrick
, p. 7635 - 7643 (2019)
A series of perylenediimide (PDI)-based multimers were synthesized using an original Suzuki–Miyaura Coupling (SMC) reaction. The new approach considers the reaction between 1-nitroPDI as the electrophilic reagent with a wide variety of boronic esters to reach PDI dimers, trimers and tetramers which are of particular interest as Non-Fullerene Acceptors (NFAs) in organic photovoltaics. In this work, we compared the reactivity of 1-bromoPDI and 1-nitroPDI towards this pallado-catalyzed cross-coupling reaction. Considering that 1-nitroPDI is more accessible in terms of selectivity, time reaction, purification efficiency, atom economy, etc, we have shown that the use of nitroarenes is largely favored in the preparation of these PDI-based multimers. The latter were characterized with determination of their spectroscopic and electrochemical properties. With the aim of extending this SMC reaction to N-annulated PDI analogues, an original and efficient transformation of nitro-PDI into pyrrole-fused PDI was found as an alternative to the well-known reductive Cadogan cyclization. The SMC reaction was applied to bromo and nitro N-annulated PDI derivatives, and DFT calculations were accomplished in order to clarify the oxidative addition step of the cross-coupling and understand the difference of reactivity between the bromo- and nitro-PDI based electrophiles.
Self-organized perylene diimide nanofibers
Yan, Ping,Chowdhury, Arindam,Holman, Michael W.,Adams, David M.
, p. 724 - 730 (2005)
A propeller-shaped perylene diimide trimer was synthesized and a simple evaporation method was used for the self-organization of trimer molecules into fluorescent nanofibers. The sizes of these fibers-from 4 to 150 nm in diameter - were measured by atomic force microscopy and can be controlled by adjusting the concentration of the initial solution. The aspect ratios (length/height) are around 500. The plane of the trimer was determined by polarized scanning confocal microscopy to be perpendicular to the axis of the fibers, in agreement with molecular mechanics calculations. UV/vis and NMR spectroscopies were used to monitor concentration-dependent π-π stacking in solution. Single-fiber fluorescence imaging and spectroscopy were performed using a total internal reflection fluorescence microscope equipped with a digital color camera and imaging CCD spectrometer. Strongly red-shifted fluorescence from these fibers indicates a high degree of electronic delocalization, and breaking up this delocalization by photobleaching blue-shifts the emission toward that of an isolated noninteracting molecule. The delocalization along these nanofibers and the ability to study the electronic structure using fluorescence make them potentially useful in nanoscale devices, such as field effect transistors and photoconductors.
Solvents Effects on Film Morphologies and Memory Behavior of a Perylenediimide-Containing Pendent Polymer
Wang, Ming,Zhang, Qi-jian,Li, Zhuang,Li, Hua,Lu, Jian-Mei
, p. 1784 - 1790 (2018)
The large polydispersity index of functional pendant polymers has hindered their application in semiconductors. Herein, a novel pendant polymer with perylenediimide (PDI) in the side chains was successfully synthesized through ring-opening metathesis poly
PDI-based heteroacenes as acceptors for fullerene-free solar cells: Importance of their twisted geometry
Chen, Huaqing,Wang, Ling,Sun, Hua,Liu, Qian,Tan, Xiao,Sang, Shenglong,Wu, Bo,Zhang, Cong,Chen, Fei,Hang, Xiao-Chun,Chen, Zhi-Kuan
, p. 13093 - 13099 (2020)
Two perylenediimide (PDI) derivatives (FP4TT2T and FP43T) with extended conjugation have been successfully synthesized. Due to their long fused D-A (D: donor and A: acceptor) molecular structures, PDI-based heteroacenes have rigid backbones and exhibit strong light absorption in the 300-600 nm range. With the contribution from the PDI moiety with strong electron affinity, the molecules possess low energy levels of LUMOs (ca. -3.7 eV), fitting well as acceptors for fullerene-free organic solar cells (OSCs). OSC devices containing FP4TT2T and FP43T were fabricated and fully characterized. It is found that the geometric twist in PDI-based heteroacenes as acceptors could enhance the performance of OSC devices. OSCs based on FP43T with a more twisted geometry achieved a power conversion efficiency of 6.05%, which is higher than those based on the FP4TT2T counterpart.
New perylenebisimide decorated cyclotriphosphazene heavy atom free conjugate as singlet oxygen generator
Okutan, Elif,Eserci, Hande,?enkuytu, Elif
, (2019)
Perylenebisimide-cyclotriphosphazene based inorganic-organic system was synthesized by a multistep procedure. The substitution reaction of asymmetric perylenebisimide (PBI) derivative with the hexachloroyclotriphosphazene (trimer) resulted in the formation of fully PBI decorated cyclotriphosphazene (5). The identity of newly synthesized compound (5) was confirmed by using 31P, 1H and 13C NMR spectroscopies and mass spectrometry. The photophysical (UV- Vis absorption, fluorescence emission, fluorescence lifetime and fluorescence quantum yield) and photochemical (the singlet oxygen generation, and photostability) properties of this conjugate were investigated as novel heavy atom free triplet photosensitizer. The singlet oxygen quantum yield of the PBI-cyclotriphosphazene (5) was calculated to be 0.86 which is good for a heavy atom free triplet photosensitizer. These results will add to the development of cyclotriphosphazene based heavy atom free singlet oxygen triplet photosensitizer systems for applications in organic oxygenation reactions.
An unusual β-oxidation of N-functionalized alkyl chains by 1H-imidazole
Langhals, Heinz,Gold, Josef
, p. 2832 - 2836 (2005)
The 1H-imidazole-mediated condensation of primary aliphatic amines with perylene-3,4: 9,10-tetracarboxylic bis-anhydride resulted in by-products where the aliphatic group was functionalized in the β-position by imidazole units.
Supramolecular Nanopatterns of Molecular Spoked Wheels with Orthogonal Pillars: The Observation of a Fullerene Haze
Grimme, Stefan,H?ger, Sigurd,Jester, Stefan-S.,Jochemich, Anna,Keller, Tristan J.,Kr?nert, Anna,Müller, Ute,Poluektov, Georgiy,Spicher, Sebastian
supporting information, p. 27264 - 27270 (2021/11/30)
Molecular spoked wheels with intraannular functionalizable pillars are synthesized in a modular approach. The functionalities at their ends are variable, and a propargyl alcohol, a [6,6]-phenyl-C61-butyrate, and a perylene monoimide are investigated. All compounds form two-dimensional crystals on highly oriented pyrolytic graphite at the solid–liquid interface. As determined by submolecularly resolved scanning tunneling microscopy, the pillars adopt equilibrium distances of 6.0 nm. The fullerene has a residual mobility, limited by the length of the flexible connector unit. The experimental results are supported and rationalized by molecular dynamics simulations. These also show that, in contrast, the more rigidly attached perylene monoimide units remain oriented along the surface normal and maintain a smallest distance of 2 nm above the graphite substrate. The robust packing concept also holds for cocrystals with molecular hexagons that expand the pillar–pillar distances by 15 % and block unspecific intercalation.
