Perylene diimides

Ling MM, Erk P, Gomez M, Koenemann M, Locklin J, Bao ZN (2007) Air-stable n-channel organic semiconductors based on perylene diimide derivatives without strong electron withdrawing groups. Adv Mater 19 1123... 

Ferrocene has been widely investigated as an electron donor and its electron donating ability can be tuned by redox reactions. As anticipated, when a ferrocene unit is covalently connected to an electron acceptor moiety that shows intrinsic fluorescence, the fluorescence of the acceptor moiety would be largely quenched because of the photoinduced electron transfer between ferrocene and the fluorescent acceptor. For instance, triad 15 that contains perylene diimide flanked by two ferrocene moieties, shows rather weak fluorescence due to the photoinduced electron transfer between perylene diimide and ferrocene units. Either chemical or electrochemical oxidation of ferrocene unit lead to fluorescence enhancement. This is simply because the electron donating ability of ferrocene is reduced after oxidation and accordingly the photoinduced electron transfer is prohibited. In this way, the fluorescence intensity of 15 can be reversibly modulated by sequential electrochemical oxidation and reduction. Therefore, a new redox fluorescence switch can be established with triad 15.25... 

Nicotinamide is an important redox moiety in biological system. The nicotin-amide-perylene diimide dyad 23 can work as a redox-responsive fluorescence switch.33 Dyad 23, in which nicotinamide is on the oxidation state, exhibits strong fluorescence. However, it becomes nonfluorescent when nicotinamide is reduced due to the electron transfer from the reduced nicotinamide to the photoexcited perylene diimide. The fluorescence of dyad 23 can be reversibly switched off and on chemically by successive reduction with NaBH3CN and oxidation with tetrachlorobenzoquinone and switched electrochemically over 10 cycles without significant degradation. 

Introduction of perfluorinated chains into the periphery of other disc-like or board-like Ji-conjugated aromatics [251, 252], such as coronene diimides [279], perylene diimides [280-282], naphthalene tetracarboxylic diimides [283-286],... 

The crystalline composites obtained between poly(3-alkylthiophene) and polystyrene showed an enhanced conductivity (07MM6579). The preparation of regioregular poly(3-alkylthiophene) and perylene diimide derivatives composites have been reported (06MI384). The photoluminescence spectra of this type of composites exhibit a significant photoluminescence quenching of the perylene diimide derivative. This result implies that the light absorbed by the perylene diimide units could also contribute to the generation of current at the photovoltaic device. 

Figure 1 Proposed mechanism for the generation of the radical anion and radical cation of perylene diimide and self-annihilation of the two to yield the triplet excited state.

Pyromellitic Diimide (PMI) Naphthalene Diimidc (NDl) Perylene Diimide (PD1)... 

Recording numerous fluorescence spectra shows a bimodal distribution of the peak position due to conformational changes within the chromophore. Attaching polyphenylene dendrons to this perylene-diimide system influences this distribution and the position of the peaks. Here, SMS was used to monitor conformational interconversions on the single-molecule level. 

R. J. Chesterfield, J. C. McKeen, C. R. Newman, P. C. Ewbank, D. Filho, J.-L. Bredas, L. L. Miller, K. Mann, and C. D. Frisbie, Organic thin film transistors based on N-alkyl perylene diimides Charge transport kinetics as a function of gate voltage and temperature , Journal of Physical Chemistry B 108, 19281 (2004). 

A.J. Breeze, A. Salomon, D.S. Ginley, B.A. Gregg, H. Tillmann, H.-H. Horhold, Polymer-perylene diimide heterojunction solar cells, Appl. Phys. Lett. 81 (2002) 3085-3087. 

Rybtchinski, B., Sinks, L.E., Wasielewski, M.R. 2004. Combining light-harvesting and charge separation in a self-assembled artificial photosynthetic system based on perylene-diimide chromophores. J. Am. Chem. Soc. 126, 12268-12269. 

In order to visualize the enzyme acting on the substrate, it was labeled with a water-soluble and highly photostable, fluorescent perylene diimide derivate (PDI) [41,42]. When labeled aPLAl ( 10 M) was added to a non-labeled POPC multilayer (stacks of bilayers), enzymes could be visualized as bright spots and areas of high enzyme localization could be clearly seen (Fig. 25.4). 

Kelly et al. remain the primary group involved in using fluorene oligomers for solar cell applications. Their initial effort utilized a fluorene oligomer, which incorporated a perylene diimide central unit (compound 68) [217],... 

Irradiation of oxygenated solutions of a-terpinene (56) in the presence of perylene diimide or 9,10-dicyanoanthracene leads to the formation of p-cymene (57) in a process which occurs by an exciplex rather than by 02( Ag) pathways. Hydroperoxy radicals may be involved in a quantum yield amplification process, and it is speculated that O2 quenching of the exciplex, or proton transfer within the exciplex, followed by trapping of the semi-reduced perylene diimide by molecular oxygen are possibilities. 

Everett TA, Higgins DA (2009) Electrostatic self-assembly of ordered perylene-diimide/ polyelectrolyte nanofibers in fluidic devices from nematic domains to macroscopic alignment. Langmuir 25(22) 13045-13051... 

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