Naphthalene tetracarboxylic diimides

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],... 

H. E. Katz, J. Johnson, A. J. Lovinger, and W. Li, Naphthalene-tetracarboxylic Diimide-based n-Channel Transistor Semiconductors Structural Variation and Thiol-enhanced Gold Contacts , Journal of The American Chemical Society 122, 7787 (2000). 

Alkyl substituted versions of naphthalene tetracarboxylic diimide (NTCDI, 46b) showed mobilities of 0.16 cmW s (R = octyl, 46c), 0.01 cmW s (R = dodecyl, 46d), and 5 x 10 3 cmW s (R = octadecyl, 46e) when measured under vacuum, but no observable electron mobility when measured in ambient. The incorporation of fiuoroalkyl groups on the side chains stabilizes NTCDI thin films and allows for n-channel operation under ambient conditions. Mobilities as high as 0.03 cmW s were obtained for 46f and 0.06 cmW s for 46g with on/off ratios on the order of... 

Starting from a 1 2 mixture of an electron-rich bis-l,5-(dinaphtho)-38-crown-10 and the electron-poor bis-acetylenic compound 1, Sanders used the template effect obtained by the inclusion of the pyromellitic diimide 1 in the crown ether to direct the oxidative coupling of the terminal alkynes toward the formation of the cyclized structure, the [2]catenane, with a 38% chemical yield. When 1 was replaced by a more electron-poor moiety obtained from 1,4,5,8-naphthalene tetracarboxylic diimide (2, Scheme 17.5) the yield of the catenane improved to 52%. 

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. 

Polyquinoxalines (11) are another group of ladder polymers. They differ from polyimidazopyrrolones by the presence of a fused six-membered cyclic diimide structure. A possible synthetic route for polyquinoxalines involves the reaction of 1,4,5,8-naphthalene tetracarboxylic acid with aromatic tetra-amines in polyphosphoric acid (PEA) at temperatures up to 220°C. 

Perylenes (70) are diimides of perylene-3,4,9,10-tetracarboxylic acid, and may be prepared by reaction of the bis-anhydride of this acid, 89 (1 mol) with the appropriate amine (2 mol) in a high-boiling solvent as illustrated in Scheme 4.11. The synthesis of perinones 71 and 72 involves condensation of naphthalene-1,4,5,8-tetracarboxylic acid with benzene-1,2-diamine in refluxing acetic acid. This affords a mixture of the two isomers, which may be separated by a variety of methods, generally involving their differential solubility in acids and alkalis. 

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). 

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