1,4,5,8-naphthalene tetracarboxylic

The proposed reduction process for 1,4,5,8-naphthalene tetracarboxylic dianhydride (NTDA)-, PMDA-, and BPDA-polyimides involves two sequential one-electron transfers to generate the radical-anion and dianion states respectively. In the case of BPDA-polymers, the formation of a diradical-dianion on the second reduction might be more energetically favored over the... 

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. 

PA-66 (50 parts)/PPE (50 parts)/SEBS (5 parts)/ 1,2,3,4-cyclopentane tetracarboxylic acid (0.5 parts) TSE at 315-321 °C/mechanical properties/PPE preextruded with acid/also used 1,4,5,8-naphthalene tetracarboxylic acid, pyromellitic dianhydride, tetrabromophthalic anhydride Grant and Jalbert 1989... 

All these dianhydrides should have a very high reactivity, because of the lower values of lumo for both the dianhydride and the monoamide. In fact, hexafluoroisopropyliden 4,4 -diphthalic anhydride should be only slightly less reactive than benzophenone tetracarboxylic dianhydride, and 2,3,6,7-naphthalene tetracarboxylic dianhydride should be very similar to biphenyl dianhydride. But if the reaction is controlled by the monoamide, as we have postulated, the most reactive dianhydride should be 1,4,5,8-naphthalene tetracarboxylic dianhydride, because lumo is almost the same than for pyromellitic dianhydride, but lumo monoamide is lower than lumo monoamide of the pyromellitic (—2.33 versus — 2.18eV). 

E.g. polycondensates from 1,4,5,8-Naphthalene tetracarboxylic dianhydride, 2,2 -Benzidinesulfonic acid and Bis[4-(3-aminophenoxy)-phenyl]sulfone [86, 87],... 

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%. 

The synthesis of BBL (poly benzimidazobenzophen-anthroline) from 1,2,4,5-tetraaminobenzeneand 1,4,5,8-naphthalene tetracarboxylic acid dianhydride (Arnold and vanDeussen [16,17]) represented a definite step forward (Scheme 4). BBL is to some extent soluble, e.g., in strongly acidic media such as sulfuric acid or meth-anesulfonic acid and can be worked into transparent films and layers. Jenekhe et al. [18] published a method... 

Suda et al. [288] reported the synthesis and characterization of a series of sulfonated star-hb polyimides (S-hb-Pls) without any crosslinking for use as proton exchange membranes. Sulfonated anhydride-terminated polyimides with different molecular weights (M v = 59,000, 200,000 and 300,000 Da) based on monomer combination 1,4,5,8-naphthalene tetracarboxylic dianhydride/4,4 -diaminobiphenyl 2,2 -disulfonic acid (NTDA/BDSA) were synthesized using different molar ratios of BDSA NTDA. The amine-terminated hb-Pl based on monomer combination 4,4-(hexafluoroisopropylidene)diphthalic anhydride/tris(4-aminophenyl)amine (6EDA/TAPA) was also prepared. Scheme 33 shows the monomer combinations used for the preparation of (S-hb-Pl). 

Direct polymerization from sulfonated monomers is the most widely used method for the synthesis of the SPIs. The synthesis is usually performed by polycondensation reaction of sulfonated diamine monomers with tetracarboxylic dianhydride monomers in m-cresol in the presence of triethyl amine (EtjN) and benzoic acid at around 180°C [4,7,10,11,13,28-34]. Sulfonated diamines are inner salts that are formed due to the interaction of the sulfonic add groups and the basic amino groups, and the function of the EtsN is to liberate the protonated amino groups of sulfonated diamines for polymerization with the 1,4,5,8-naphthalene tetracarboxylic dianhydride (NTDA),... 

Dimethyl acetylenedicarboxylate (DMAD) (125) is a very special alkyne and undergoes interesting cyclotrimerization and co-cyclization reactions of its own using the poorly soluble polymeric palladacyclopentadiene complex (TCPC) 75 and its diazadiene stabilized complex 123 as precursors of Pd(0) catalysts, Cyclotrimerization of DMAD is catalyzed by 123[60], In addition to the hexa-substituted benzene 126, the cyclooctatetraene derivative 127 was obtained by the co-cyclization of trimethylsilylpropargyl alcohol with an excess of DMAD (125)[6l], Co-cyclization is possible with various alkenes. The naphthalene-tetracarboxylate 129 was obtained by the reaction of methoxyallene (128) with an excess of DMAD using the catalyst 123[62],... 

NaOH-catalyzed resole resin, 409 Naphthalene diisocyanate (NDI), 201 Naphthalene tetracarboxylic dianhydride (NDTA), 282... 

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. 

A different synthetic route involves halogenation (bromination, chlorination) of pyrene 77, which is thus converted to the tetrahalogen derivative. Oxidation with sulfuric acid to form a diperinaphthindandione with subsequent oxidation, once again in a sodium hydroxide solution [7], yields the tetra sodium salt of naphthalene tetracarboxylic acid 78 ... 

The synthetic route to perinone pigments, as to perylene pigments, starts from an anhydride, in this case from the monoanhydride of naphthalene tetracarboxylic acid. 

Perinones are structurally similar to perylenes being made by condensing naphthalene tetracarboxylic dianhydride with amines, but in this case 1,2-diamines, e.g. Cl Pigment Orange 43 (2.71), or its cis isomer. The isomers can be separated by fractionation of their salts. They offer orange to bordeaux shades with similar properties to perylenes, but are less commercially important. 

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). 

Lead compounds such as lead naphthalene tetracarboxylate, lead pyrophosphate, lead stannate, lead sulfide, and others which are not listed in Table 3, were proved to be effective uranium sorbents in sea water 131). However, sorbent materials containing toxic metals must be excluded with respect to sea contamination which would be inevitable even in the case of slight solubility. On the other hand, many metal compounds are decomposed in sea water by hydrolysis and carbonate formation. Among the inorganic sorbents presented in Table 3, hydrous titanium oxide and... 

NTCDA naphthalene tetracarboxylic dianhydride PTCDA perylene tetracarboxylic dianhydride... 

Figure 14-20. Molecular structure of naphthalene tetracarboxylic dianhydride (NTCDA) and perylene tetracarboxylic dianhydride (PTCDA).

Another interesting feature in the data given in Table 14-3 is the different mobility reported for NTCDA (naphthalene tetracarboxylic dianhydride) and PTCDA (perylene tetracarboxylic dianhydride). These two compounds present very similar molecular formulae (Fig. 14-20), but differ by their crystal packing... 

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... 

Not all attempts at formations of ladder polymers yielded completely cyclized fused ring structures. For instance, an attempt to form a polymer from tetraaminonaphthalene with naphthalene tetracarboxylic acid dianhydride failed to yield complete cyclizations [222]. 

Kim Woo-Sik, Kim Sang-Youl (1997). Synthesis and properties of polyesters containing naphthalene tetracarboxylic imide, > 99-102. 

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