Perylene tetracarboxylic derivatives

CuPC p-type)/perylene tetracarboxylic derivative (n-type)/Ag ... 

Production of a two-layer film made out of copper phthalocyanine and a perylene tetracarboxylic derivative. A power conversion efficiency of about 1% has been achieved. 

Figure 8 Molecular structures of some interesting materials (a) copper phthal-ocyanine (CuPc) (b) perylene tetracarboxylic derivative (PV) (c) hydroxysquarylium (d) merocyanine dye.

Perylene Tetracarboxylic Derivatives with Varying Alkyl Chain Length Film Packing and Surface-Enhanced Fluorescence Studies, Langmuir 17,2958-2964 (2001). 

The first organic tandem solar cell was published in 1990 by Hiramoto et al, who employed two identical subcells composed of bilayers of a metal-free phthalocyanine and a perylene tetracarboxylic derivative with an ultrathin Au layer to interconnect the two subcells to achieve an almost doubling of the voltage. More than a decade later, in 2002, Forrest et reported on two, three, and five stacked heterojunction cells consisting of copper phthalocyanine (CuPc) as a donor and perylenetetracarboxylic bis-benzimidazole (PCTBI) as an acceptor. Ultrathin ( 5 A) layers of Ag clusters were placed between the heterojunctions to interconnect the subcells. Similar results were described by Tsutsui et In 2004, Leo and Pfeifer et intro-... 

Redox molecules are particularly interesting for an electrochemical approach, because they offer addressable (functional) energy states in an electrochemically accessible potential window, which can be tuned upon polarization between oxidized and reduced states. The difference in the junction conductance of the oxidized and the reduced forms of redox molecules may span several orders of magnitude. Examples of functional molecules used in these studies include porphyrins [31,153], viologens [33, 34,110,114,154,155], aniline and thiophene oligomers [113, 146, 156, 157], metal-organic terpyridine complexes [46, 158-163], carotenes [164], nitro derivatives of OPE (OPV) [165, 166], ferrocene [150, 167, 168], perylene tetracarboxylic bisimide [141, 169, 170], tetrathia-fulvalenes [155], fullerene derivatives [171], redox-active proteins [109, 172-174], and hydroxyquinones [175]. 

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. 

Most pigments derived from vat dyes are structurally based on anthraquinone derivatives such as indanthrone, flavanthrone, pyranthrone, or dibromoan-thanthrone. There are other polycyclic pigments which may be used directly in the form in which they are manufactured. This includes derivatives of naphthalene and perylene tetracarboxylic acid, dioxazine (Carbazole Violet), and tetrachloro-thioindigo. Quinacridone pigments, which were first introduced in 1958, and recently DPP pigments have been added to the series. 

Dibromoanthanthrone is a vat type pigment which demonstrates excellent fastness properties, a feature which is an asset in high grade paints. It provides a clean yellowish shade of scarlet, somewhere between that of P.O.43, a naphthalene tetracar-boxylic acid derivative, and those of yellowish perylene tetracarboxylic acid type pigments. 

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. 

Several methods have been reported for the monofunctionaUzation of PDI [6] including one-pot imidization (route A) or a base-promoted coupling reaction between naphthalene monoimide derivatives (route B) [7], as shown in Scheme 2. We found the one-pot imidizatitMi reaction (route A) to be more practical than route B route B consisted of five steps and the open-form product 6b was labile under the basic reaction conditions required to produce the closed product 6a. The one-pot imidization, route A, was simple and 3 could easily be recovered via column chromatography because the use of an excess amount of 3 was necessary. Concerning the solubility and reactivity of perylene tetracarboxylic acid dianhydride (PDA) 4, the imidization of 4 was, first, carried out with 2,6-ditsopropylaniline (5) in imidazole then 3 in propionic acid solution was added to produce the closed product PDI 6a. 

Another, less direct, approach to manipulate molecules on a surface is through the use of chemical self-assembly principles derived from X-ray crystallographic work. A two-dimensional hydrogen bonding motif derived from crystal-engineering studies has been used to assemble a two-dimensional honeycomb lattice based on the hydrogen bonded triad motif formed between perylene tetracarboxylic acid diimide (5.1) and melamine (5.2). The honeycomb... 

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 and perinone pigments are chemically related. The group of perylene pigments is derived from perylene-3,4,9,10-tetracarboxylic acid 67, while perinone pigments are derivatives of napthalene-l,4,5,8-tetracarboxylic acid 68 ... 

Conceptually similar are single-layer photoreceptors such as PVK filled with a photoconductive pigment, such as IV,IV-di(3,5-dimethylphenyl)perylene-3,4,9,10-tetracarboxylic acid diimi.de (32), or a photoconductor containing a bisazo photoconductive pigment, a hole transporting molecule such as an indolinyl hydrazone derivative of carbazole shown in Fig. 5i, in a polyester binder (33). In practice, this photoconductor is charged positively even though both holes and electrons are mobile. 

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