Quaterrylene diimides

The first synthesis of quaterrylene diimides 70 bearing solubilizing alkyl or alkylphenyl groups was achieved in 1995 [110]. This led to the development of higher perylene diimide homologs with strongly bathochromically shifted UV/visible absorption characteristics (Scheme 13.20) [111-114]. 

Lee SK, Zu Y, Herrmann A, Geerts Y, MAllen K, Bard AJ (1999) Electrochemistry, spectroscopy and electrogenerated chemiluminescence of petylene, terrylene, and quaterrylene diimides in aprotic solution. J Am Chem Soc 121(14) 3513-3520... 

Oh JK, Lee WY, Noe T, Chen WC, Kdnemann M, Bao Z (2011) Solution-shear-processed quaterrylene diimide thin-film transistors prepared by pressure-assisted thermal cleavage of swallow tails. J Am Chem Soc 133 4204-4207... 

Scheme 4.24 Synthesis of quaterrylene diimides (i) Ni (ii) K2CO3 (iii) tert.-BuONa...

Mullen and co-workers extended the synthesis of perylene discotics to various other core-enlarged perylene dyes, such as terrylene and quaterrylene diimides [158]. An example of quaterrylene diimides synthesis is shown in Scheme 4.24. 

Figure 13.3 Chemical structures of rylene diimides (perylene, n = 0 terrylene, n = 1 quaterrylene, n = 2 pentary-lene, n = 3 hexarylene, n = 4).

Scheme 13.20 Synthesis of quaterrylene and terrylene diimides 70 and 74, respectively.

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