22513-16-2Relevant articles and documents
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.
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.
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.
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.
