Naphthalenediimides

PAMAM dendrimers of generations one to five were decorated on the periphery with naphthalenediimide units (Fig. 6.47) carrying cationic substituents assuring solubility in water. Subsequent reduction with sodium dithionite or forma-mide in aqueous medium [90] led to anion radical sites at the diimide units. These aggregate in solution to form -stacks in the solid state they form electrically conductive films [91]. 

The nematic LC is the original eutectic mixture of 35% (weight %) 4 (m-octyl oxy)-4-cyanobiphenyl (80CB) and 65% 4/-(n-pentyl)-4-cyanobiphenyl (5CB). The sample is doped with perylene and 2% (mol %) of NIAC, which is acrylate monomer containing the easily reduced l,4 5,8-naphthalenediimide moiety (see Scheme 3). Finally, 0.5% (mol %) of benzoin methyl ether (BME) is added to photoinitiate polymerization of the NIAC. 

Naphthalenediimides as Photoactive and Electroactive Components in Supramolecular Chemistry... 

Figure 11.1 General structure of pyromellitic diimides, naphthalenediimide, and perylenediimide compounds (R = aryl, alkyl).

Recently, new insight into detailed mechanisms of photochemical processes in donor-acceptor pairs (DA) has emerged. To study the role of bridge energy levels on electron transfer rates, a series of rod-like donor-bridge-acceptor (D-B-A) molecules in which a 4-aminonaphthalene-l,8-imide (ANI) electron donor is linked to a 1,8 4,5-naphthalenediimide acceptor (NI) via the 1,4 positions on a phenyl bridge was... 

A planar chiral naphthalenediimide cyclophane (39) and its derivatives were prepared for their tunable intramolecular FRET properties. The enantiomeric enrichment of cyclophane 39 was accomplished by chiral HPLC (on a Daicel IA column) and the CD spectra of enantiomeric 39 were reported (Fig. 9) [51]. 

Fig. 9 The CD spectra of chiral naphthalenediimide cyclophane 39 in dichloromethane. Solid lines experimental spectra for enantiomerically enriched samples (concentration 8.1 and 7.0 pM for first and second peaks, respectively). Dotted lines spectra of pure enantiomers corrected for the enantiomeric purities of the sample obtained by chiral HPLC. Reprinted with permission from [50]. Copyright 2009 Royal Society of Chemistry...

Gabutti S, Schaffner S, Neuburger M, Fischer M, Schafer G, Mayor M (2009) Planar chiral asymmetric naphthalenediimide cyclophanes synthesis, characterization and tunable FRET properties. Org Biomol Chem 7 3222-3229... 

Solid State Characterisation of a-Amino Acid Functionalised Naphthalenediimides. Nanotube Characterisation. 

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