Naphthalene bisimides

Wtirthner, F., Ahmed, S., Thalacker, C. and Debaerdemaeker, T. (2002) Core-substituted naphthalene bisimides New fluorophores with tunable emission wavelength for FRET studies. Chemistry-A European Journal, 8, 4742-50. 

K. Nakabayashi, H. Mori, All-Polymer Solar Cells Based on Fully Conjugated Block Copolymers Composed of Poly(3-Hexylthiophene) and Poly(Naphthalene Bisimide) Segments. Macromolecules 2012, 45, 9618-9625. 

NIR fluorophores are generally considered as substances that emit fluorescence in the NIR region (650-900 nm). Particularly, the fluorescence quantum yield (QY) of NIR fluorophores is always lower than that of short wavelength emission ones. Over the past few decades, enormous progress has been made in the field of NIR fluorescent dyes. There are several major NIR organic fluorescent chromophores, such as bay-substituted perylene or naphthalene bisimides, cyanine dyes, BODIPYs, DPPs, and porphyrins. 

Figure 5.2 Target sensors PND and PNT for Zn based on N-core substituted naphthalene bisimides as NIR chromophore.

Hydrogen bonds can also be used to control the morphology of imsym-metrically substituted naphthalene bisimides in organic field-effect transis-... 

The primary starting material for the synthesis of perylene tetracarboxylic acid pigments is the dianhydride 71. It is prepared by fusing 1,8-naphthalene dicar-boxylic acid imide (naphthalic acid imide 69) with caustic alkali, for instance in sodium hydroxide/potassium hydroxide/sodium acetate at 190 to 220°C, followed by air oxidation of the molten reaction mixture or of the aqueous hydrolysate. The reaction initially affords the bisimide (peryldiimide) 70, which is subsequently hydrolyzed with concentrated sulfuric acid at 220°C to form the dianhydride ... 

Indeed, besides the perylene tetracarboxylic dianhydride (PTDA) used by Lee et al. [54] and the bisimide dianhydride synthesized by Kim [55], only two new naphthalenic dianhydrides have been described. In this respect, 4,4 -ketone dinaphthalene l,l, 8,8 -tetracarboxyUc dianhydride (KDNTDA, Fig. 3) is obtained through a multistep synthesis, with a 19% overall yield [56]. 

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