Perylene diimide derivatives

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... 

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. 

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). 

The compounds with the highest electron mobility are currently fullerene C60 [81, 82] and N,N4-dialkyl-3,4,9,10-perylene tetracarboxylic diimide derivatives [83, 84], with values up to 0.5 cm2 V 1 s 1. A major problem with these compounds is their high sensitivity to ambient conditions, especially oxygen and moisture. A small number of air-stable n-type compounds have been reported [85-88]. All are perfluorinated and their mobility does not exceed a few tenths of 1 cm2 V 1 s 1. 

The perylene derivatives are n-t3rpe organic semiconductors. They are of great interest as components for organic electronics. In particular, films of perylenetetracarboxylic diimide derivative (PTCDI) are used as n-layers in heterojunctions of organic solar cells [1]. The industrial application of these materials is now limited by insufficient knowledge about conductivity mechanisms and their correlation with structural features of the films. 

Table 14.1 presents a selection of donor/acceptor combinations that have shown notable solar cell efficiencies. Power conversion efficiencies of 1.5-2.2% have been demonstrated for a number of systems, with most blends utilizing either a CN-PPV derivative or the fluorene-dithienylbenzothiadiazole copolymer F8TBT as the acceptor. Despite their high electron mobilities, perylene diimide- and naphthalene diimide-based acceptors have shown disappointing efficiencies, though with optimization Zhou et al. have recently been able to achieve a power conversion efficiency of 2.2% with a perylene diimide acceptor [25]. 

Figure 43 Liquid crystalline coronene derivative and perylene diimide used to produce self-organized donor/acceptor architectures for organic solar cells. °...

Perylene diimide and its derivatives are well-known as photofunctional dyes with unique optical and electrochemical properties. They have excellent light fastness, high chemical stabiUty, high photoluminescence yield, and... 

Perylene and perinone pigments are closely related chemically and are manufaemred by essentially the same route. Perylenes are diimide derivatives of perylene-3,4,9,10-tetracarboxylic acid, while perinones are derivatives of naphthalene-1,4,5,8-tetracarboxylic acid (Herbst and Hunger, 1997). 

Horowitz, G., Kouki, R, Spearman, P, Fichou, D., Nogues, C., Pan, X., Gamier, R Evidence for n-type conduction in a perylene tetracarboxylic diimide derivative. Adv. Mater. 8,242-245 (1996)... 

Malenfant, P.R.L., Dimitrakopoulos, C.D., Gelorme, J.D., Kosbar, L.L., Graham, T.O., Curioni, A., Andreonr, W. iV-type organic thin-film transistor with high field-effect mobility based on a N, N -dialkyl-3,4,9,10-perylene tetracarboxylic diimide derivative. Appl. Phys. Lett. 80, 2517-2519 (2002)... 

Perylene pigments include the dianhydride and diimide of perylene tetracarboxylic acid along with derivatives of the diimide while perinone pigments are derived from naphthalene tetracarboxylic acid. 

The principal chromophores in pseudo sulfur dyes are copper and cobalt phthalocyanines, e.g., in C.I. Sulphur Green 25 (16), and the perylene tetracar-boxylic diimide structure in C.I. Sulphur Red 14 [81209-07-6] and C.I. Solubilised Sulfur Red 11 [61969-41-3] (17). In contrast to the sulfur dye made from Cu phthalocyanine, the cobalt derivative can be applied with dithionite. 

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