Naphthalene-l,4,5,8-tetracarboxylic

A new quality in ladder polymer synthesis via multifunctional polycondensation was reached in the late 1960s when poly(benzimidazobenzo-phenanthroline) (BBL) 12 was prepared by Arnold and van Deusen [21 -24]. The polymer was synthesized from naphthalene-l,4,5,8-tetracarboxylic acid dianhydride (11) and 1,2,4,5-tetraaminobenzene (la) in strong acidic media (polyphosphoric acid, sulfuric acid). BBL is completely soluble in concentratal sulfuric acid or methanesulfonic add and is processible into durable films and... 

In contrast, polynaphthoylenebenziniidazote based on 2,2-bis(3,4-diaminophenyl) hexafluoropropane are soluble not only in H2SO4, m-cresol and a tetrachloroethane-phenol mixture (3 1) (this is characteristic for polymers derived from bis(o-phenylenediamine) and naphthalene-l,4,5,8-tetracarboxylic acid dianhydride [183, 184]) but also in N-MP (N-methylpyrolidane). An enhanced solubility of polynaphthoyleiKbenzimidazoles of this series is explained not only by the introduction of a hinge group between naphthalic anhydride moieties, but also by low viscosity characteristics of the systems caused by low basicity of 2,2-bis(3,4-diaminophenyl)hexafluoropropane [185],... 

Naphthalene-l, 4,5,8-tetracarboxylic acid dianhydride 118, 137, 138, 140, 146, 147 2,6-Naphthalenedicarboxylic acid 196 Nonlinear optical polymers 36... 

Another class of polyimides that are characterised by a higher chain flexibility, when compared to PPI, are based on naphthalene-l,4,5,8-tetracarboxylic acid dianhydride (DNTA). These polymers are of considerable interest due to their high heat resistance and thermal stability and due to easy accessibility of the starting monomers. DNTA is a widely available dianhydride showing the highest electrophilic reactivity among bisfnaphthalene-tetracarboxylic anhydrides [18, 19]. 

Naphthalene-1,8-dicarboxylic add, its nitro-substituted derivatives, and naphthalene-1,4,5,8 tetracarboxylic acid, on treatment with sulfur tetrafluoride at 0 C, undergo dehydration to form quantitatively the corresponding anhydrides [218, 221] Unsubstituted and mononitrated monoanhydndes react further at 200-250 °C to give derivatives of 1,1,3,3-tetrafluoro-l// naphtho[I,8 c,d]pyran Dinitronaphthalene-l,8-di-carboxyhc acid anhydndes and naphthalene 1,4,5,8 tetracarboxylic acid dianhydnde give the respective tetra- and octafluoroethers only in the presence of an excess of anhydrous hydrogen fluoride [221] (equabons 113 and 114)... 

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%. 

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