22513-16-2Relevant academic research and scientific papers
Synthesis, characterization, and photophysical study of fluorescent N-substituted benzo[ghi]perylene "swallow tail" monoimides
Manning, Steven J.,Bogen, William,Kelly, Lisa A.
, p. 6007 - 6013 (2011)
A set of N-substituted benzoperylene monoimide (BPI) fluorophores was synthesized and characterized structurally and photophysically. Condensation of benzo[ghi]perylene-1,2-dicarboxylic anhydride in the presence of "swallow tail" alkyl amines produced fluorophores that are soluble in a range of organic solvents, highly absorbing in the near-UV (ε334 = 79 000 M-1cm-1), and fluorescent in the visible range. Photophysical behavior of the compounds was studied with steady-state and time-correlated single photon counting. The synthesized BPIs exhibit positive solvachromatic emission (λem (hexane) = 469 nm; λem (ethanol) = 550 nm) as a function of solvent polarity with little change in their excited-state lifetime (9.6-6.5 ns) and fluorescence quantum yield (0.27-0.44) over the polarity range studied. Solvachromatic shifts were analyzed using the Lippert-Mataga approach. In nonpolar hydrocarbon solvents evidence of dual emission from closely spaced (562 cm-1) S1 and S2 excited states is observed. Preliminary peak assignments for the anomalous S2 emission are made.
Ultralong nanobelts self-assembled from an asymmetric perylene tetracarboxylic diimide
Che, Yanke,Datar, Aniket,Balakrishnan, Kaushik,Zang, Ling
, p. 7234 - 7235 (2007)
Ultralong nanobelts (>0.3 mm) have been fabricated from an asymmetric perylene tetracarboxylic diimide (PTCDI) molecule via a seeded self-assembly processing. The long length of nanobelts facilitates the construction of two-electrode devices employing the nanobelt as channel material, and the long-range one-dimensional π-π molecular stacking allows for efficient conductivity modulation through surface doping. A combination of these two characters enables efficient electrical sensing of reducing VOCs using the nanobelt. As examined for hydrazine, more than 3 orders of magnitude increase in current was observed for a single nanobelt when exposed to the saturated vapor of hydrazine. Copyright
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.
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 (2020/11/03)
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 cyclotriphosphazene based nanotweezers bearing perylene and glycol units and their non-covalent interactions with single walled carbon nanotubes
Eserci, Hande,?enkuytu, Elif,Okutan, Elif
, p. 1 - 8 (2019/01/28)
We report on the design, synthesis and characterization of three new amphiphilic four fragment cyclotriphosphazene nanotweezers based on thermally stable carrier/router cyclotriphosphazene, extended polycyclic aromatic perylene bisimides with hydrophobic aliphatic tail and solvophilic glycol units, suitable for the exfoliation of single-walled carbon nanotubes (SWCNTs). The ultrasonication of SWCNT and new cyclotriphosphazene derivatives provided disentangled and undamaged SWCNTs, which interact with the perylene units through π–π interactions. The newly synthesized perylene-cyclotriphosphazenes were characterized by elemental analysis, mass, 31P, 1H and 13C NMR techniques. The photophyisical behavior of cyclotriphosphazene derivatives and their nanocomposites were investigated via UV– Vis absorption and fluorescence emission spectroscopy. It was found that non-geminal- cis-tris- perylenebisimide substituted compound exhibit an additional fluorescence peak compared with the parent compounds which is consistent with an intramolecular excimer formation. Prepared nanocomposites were also characterized via Raman spectroscopy and the morphological features were analyzed by HR- TEM. The quality of the nanocomposite dispersions in water were evaluated by zeta potential analysis.
Encapsulation induced aggregation: a self-assembly strategy for weakly pi-stacking chromophores
Sao, Soumik,Mukherjee, Ishita,De, Priyadarsi,Chaudhuri, Debangshu
supporting information, p. 3994 - 3997 (2017/04/11)
Molecular assembly of weakly pi-stacking core-substituted naphthalene diimides (cNDIs) requires the participation of strong side-group interactions. Spatial confinement within a micellar core leads to locally elevated concentrations and reduced entropy that drives a rapid aggregation, often followed by a slower aggregate reorganization. Fast aggregation kinetics leads to self-sorting of aggregates.
Energy transfer in pendant perylene diimide copolymers
Davis, Nathaniel J.L.K.,Macqueen, Rowan W.,Roberts, Derrick A.,Danos, Andrew,Dehn, Sabrina,Perrier, Sébastien,Schmidt, Timothy W.
supporting information, p. 8270 - 8275 (2016/09/09)
We report the synthesis, characterisation and polymerisation of two novel asymmetric perylene diimide acrylate monomers. The novel monomers form a sensitiser-acceptor pair capable of undergoing F?rster resonance energy transfer, and were incorporated as copolymers with tert-butyl acrylate. The tert-butyl acrylate units act as spacers along the polymer chain allowing high concentrations of dye while mitigating aggregate quenching, leading to persistent fluorescence in the solid state at high concentrations of up to 0.3 M. Analysis of fluorescence kinetics showed efficient energy transfer between the optically dense sensitiser and the lower concentration acceptor luminophores within the polymer. This reduced reabsorption within the material demonstrates that the copolymer-scaffold energy transfer system has potential for use in luminescent solar concentrators.
Supramolecular Organization of Dye Molecules in Zeolite L Channels: Synthesis, Properties, and Composite Materials
Cao, Pengpeng,Khorev, Oleg,Devaux, André,S?gesser, Lucie,Kunzmann, Andreas,Ecker, Achim,H?ner, Robert,Brühwiler, Dominik,Calzaferri, Gion,Belser, Peter
supporting information, p. 4046 - 4060 (2016/03/16)
Sequential insertion of different dyes into the 1D channels of zeolite L (ZL) leads to supramolecular sandwich structures and allows the formation of sophisticated antenna composites for light harvesting, transport, and trapping. The synthesis and properties of dye molecules, host materials, composites, and composites embedded in polymer matrices, including two- and three-color antenna systems, are described. Perylene diimide (PDI) dyes are an important class of chromophores and are of great interest for the synthesis of artificial antenna systems. They are especially well suited to advancing our understanding of the structure-transport relationship in ZL because their core fits tightly through the 12-ring channel opening. The substituents at both ends of the PDIs can be varied to a large extent without influencing their electronic absorption and fluorescence spectra. The intercalation/insertion of 17 PDIs, 2 terrylenes, and 1 quaterrylene into ZL are compared and their interactions with the inner surface of the ZL nanochannels discussed. ZL crystals of about 500 nm in size have been used because they meet the criteria that must be respected for the preparation of antenna composites for light harvesting, transport, and trapping. The photostability of dyes is considerably improved by inserting them into the ZL channels because the guests are protected by being confined. Plugging the channel entrances, so that the guests cannot escape into the environment is a prerequisite for achieving long-term stability of composites embedded in an organic matrix. Successful methods to achieve this goal are described. Finally, the embedding of dye-ZL composites in polymer matrices, while maintaining optical transparency, is reported. These results facilitate the rational design of advanced dye-zeolite composite materials and provide powerful tools for further developing and understanding artificial antenna systems, which are among the most fascinating subjects of current photochemistry and photophysics. Rylenes in nanochannels: The synthesis and properties of organic dyes incorporated into zeolite L (ZL) crystals are described. The intercalation/insertion of 17 perylene diimides, two terrylene diimides, and one quaterrylene diimide into ZL is compared and their interactions with the inner surface of the ZL nanochannels are discussed (see figure).
Tetrahedral rigid core antenna chromophores bearing bay-substituted perylenediimides
Myahkostupov, Mykhaylo,Castellano, Felix N.
supporting information, p. 9519 - 9527 (2015/12/01)
Two new representative methane- and adamantane-centered 'antenna' tetramers bearing bay-substituted π-conjugated phenylethynyl-perylenediimides (PDICCPh) as chromophoric subunits, tetrakis-[1-(4-ethynylphenyl)-N,N′-bis(1-hexylheptyl)-perylene-3,4:9,10-tetracarboxylic diimide]-methane (1) and tetrakis-1,3,5,7-[1-(4-ethynylphenyl)-N,N′-bis(1-hexylheptyl)-perylene-3,4:9,10-tetracarboxylic diimide]-adamantane (2), have been synthesized and their structural aspects have been thoroughly investigated by NMR spectroscopy. These PDI tetramers (1 and 2) represent the first successful example of incorporating the bay-substituted phenylethynyl-perylenediimides into the large rigid core tetrahedral frameworks. In these PDI tetramers, dynamic NMR experiments revealed the existence of perylene-centered conformational dynamic equilibrium (ΔG≠=15-17 kcal/mol), the primary cause of the observed spectral broadening in conventional 1H NMR spectra (295 K). In addition, PDI tetramers 1 and 2 were found to possess exceptional (photo)chemical stability, and their corresponding photophysical properties (εmax～180,000; τFL=6.9 ns; ΦFL～60%) make them viable candidates for various photonic applications and are in good agreement with other related multichromophoric PDI-based systems.
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
supporting information, p. 13756 - 13759 (2015/09/07)
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.
