Perylene tetracarboxylic diimides

Beton and co-workers extended the hydrogen bonding approach to two-component systems, generating a number of structures that utilise different molecular motifs.24 26 In the case of perylene tetracarboxylic diimide (PTCDI) co-adsorbed with melamine (1,3,5-triazine-2,4,6-triamine) on a silver-terminated silicon surface, a network is formed in which the straight edges correspond to PTCDI with melamine at the vertices (Figure 11.6). The network shows large-area pores that the authors used to trap heptamers of C6o molecules. 

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. 

Horowitz, G. et al.. Evidence for n-type conduction in a perylene tetracarboxylic diimide... 

The process for the thennal sensor network is as follows. Organic diodes, to be used as sheet-type thermal sensors, are manufactured on an ITO-coated PEN film. A 30-mn thick p-type semiconductor of copper phthalocyanine (CuPc) and a 50-nm thick n-type semiconductor of 3,4,9,10-perylene-tetracarboxylic-diimide (PTCDI) are deposited by vacuum sublimation. A 150-mn thick gold film is then deposited to form cathode electrodes having an area of 0.19 mm. The film with the organic diodes is coated with a 2-pm thick parylene layer and the electronic interconnections are made by the method similar to that mentioned before. The diode film is also mechanically processed to form net-shaped structures. Finally, to complete the thermal sensor network, we laminated the transistor and diode net films together with silver paste patterned by a microdispenser. This is shown in Figure 6.3.11. 

H-bonding interactions are also suitable for assembling multi-component networks. In an illustrative example, melamine [17, 22], a H-bonded molecule with threefold symmetry, was assembled together with perylene tetracarboxylic diimide (PTCDI) [23]. These molecules interact strongly via complementary triple H-bonds. A hexagonal network with pores that have a size of approximately 2 nm were... 

Perylene tetracarboxylic dianhydride and 3,4,9,10-Perylene tetracarboxylic diimide... 

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 customary method of preparing perylene pigments is by reaction of perylene tetracarboxylic dianhydride with primary aliphatic or aromatic amines in a high boiling solvent. The dianhydride itself is also used as a pigment. Di-methylperylimide may also be obtained by treating the diimide with methyl chloride or dimethyl sulfate. 

A different route proceeds by alkali fusion of the corrspondingly substituted naphthalic acid imide. This pathway parallels the synthesis of perylene tetracarboxylic acid diimide 70 (Sec. 3.4.1.1). The method is particularly suited to aliphatic amines. 

Perylene tetracarboxylic acid dimethylimide may also be prepared by methylating the corresponding diimide. 

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],... 

Perylene pigments n. A group of vat pigments, nearly all of which are N,N -sub-stituted peryzene-3,4,9,10-tetracarboxylic diimides. Scarlet and vermilion varieties, resistant to bleeding, light, heat, and chemicals are used in plastics. 

Metal complexes of 2,9,16,23-tetrasulfophthalocyanines Riboflavin 5 -phosphate N, N -Bis(ethylenesulfate)-3,4,9,10-perylene tetracarboxylic acid diimide Ru(NCS) Me2bpy)(2,2 5, 2"-terpy-4-phosphonic acid) " "... 

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... 

Perylenes are chemically diimides of perylene tetracarboxylic acid. The shade change is dependent on the substitution of the imide nitrogen (4). 

Conversion of Perylenes Acenaphthene to Perylene Tetracarboxylic Acid Diimide (PTCI, Pigment Violet 29)... 

The third reaction stage is the most important and complex in the sequence, and is an alkaline fusion reaction. This is the synthesis stage in which the perylene chromophore is chemically formed, as well as the step in which many of the important physical properties of perylene tetracarboxylic acid diimide (PTCI) are determined. In the fusion reaction, (4) is fused with itself via a bimolecular nucleophilic substitution in the presence of molten alkali at temperatures in excess of 200 C. The resulting alkaline mass is then precipitated by slowly mixing into water. The subsequent slurry contains perylene in its reduced (leuco) form or salt. One of the several possible isomers of the lenco form is represented with the general formula (5). 

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