1,4,5,8-Naphthalenetetracarboxylic dianhydride

Nollau A, Pfeiffer M, Fritz T, Leo K (2000) Controlled n-type doping of a molecular organic semiconductor naphthalenetetracarboxylic dianhydride (NTCDA) doped with bis (ethylenedithio)-tetrathiafulvalene (BEDT-TTF). J Appl Phys 87 4340... 

Photolysis of 1,2,3,4- and 1,2,4,5-benzenetetracarboxylic dianhydride with different wavelengths invariably results in formation of hexatriyne 125. Attempts to isolate 1,2,5,6- and 2,3,6,7-tetradehydronaphthalenes (naphthdiynes) by photolysis of the corresponding naphthalenetetracarboxylic dianhydrides yield only acetylenic compounds, which suggests that naphthdiynes are formed, but rapidly decompose under photochemical conditions. 

Using naphthalenetetracarboxylic dianhydride as the semiconductor, changes in bulk conductivity, field-effect mobility, and threshold voltage were separately observed in response to exposure to water and oxygen [35, 36], Another more elaborate kind of pattern was produced by a virtual array of eleven different semiconductor OFET monitoring on-current in response to polar and nonpolar organic vapors [37]. Responses (0.8-0.3-fold reductions and 1.5-2-fold increases) were dis-... 

The method described above and outlined in Scheme 1 is particularly suitable for the synthesis of symmetrically substituted NDIs but originally it was of limited value for the synthesis of naphthalenemonoimide (NMI) and N-desymmetrised NDI derivatives. This is due to the difficulty of selective imide formation in a cross-conjugated dianhydride containing two equivalent electrophilic sites such as 1,4,5,8-naphthalenetetracarboxylic dianhydride (NDA). For all the aliphatic amines and amino acids tested, carrying out the reaction for 5 min at 140 °C only led to the formation of a 1 2 1 statistical mixture of dianhydride monoimide diimide (Table 1). 

FIGURE 7.20. Crystal data for the molecular complex of anthracene with 1,8 4,5-naphthalenetetracarboxylic dianhydride.[Remarks in brackets). 

C26H12N2O10S2 polyimide based on (1,4,5,8-naphthalenetetracarboxylic dianhydride) and (diphenyl-disulfonic acid) diamine 105... 

C27H14N206 polyimide based on 1,4,5,8-naphthalenetetracarboxylic dianhydride and di(hydroxyphenyl)-methane-diamine 217... 

For polyimides derived from p-phenylenediamine and a variety of dianhydrides, the order of stability with respect to the dianhydride is pyromellitic dianhydride > 3,3, 4,4 -benzophenonetetra-carboxylic anhydride > l,3-bis(3,4-dicarboxyphenyl)hexafluoro-propane dianhydride > 1,4,5,8-naphthalenetetracarboxylic dianhydride. 

Thesulphonatedpolyimidemembranesarebasedon4,4 -diaminobiphenyl-2,2 -disulphonic acid (BDSA), 4,4 -oxydianiline (ODA), 4,4 -oxydiphthalic anhydride (ODPA) and 1,4,5,8-naphthalenetetracarboxylic dianhydride (NTCDA). The study of the surface properties of fluorinated polyimides exposed to vacuum ultraviolet (VUV) radiation and atomic oxygen may help us understand the stability of these polymers. It will also be interesting to apply this sulphonation method to some novel high molar mass poly-etherimide, as reported by Hsio and Yang (1997). 

Sato, X, Niino, H., and Yabe, A, Reactive intermediates formed by the consecutive photolyses of naphthalenetetracarboxylic dianhydrides direct observation of reactive intermediates generated by laser-induced reaction in low-temperature argon matrices, /. Photochem. Photobiol. A Chem., 145, 3, 2001. 

---