4,5-Diphenoxybenzene-1,2-dicarbonitrile

Abstract

In the title compound, C20H12N2O2, the phenyl and benzene rings are mutually perpendicular, with the dihedral angle between the phenyl rings being 87.92 (16)° and those formed between the phenyl rings and the benzene rings being 73.68 (15) and 84.65 (15)°. Helical supra­molecular chains along [010], mediated by C—H⋯N inter­actions, are found in the crystal structure.

4-(Prop-2-yn-1-yloxy)benzene-1,2-dicarbonitrile

“…For the solubilization and some applications of phthanocyanine dyes, see: Jiang et al (2011); Sleven et al (2001). For the synthesis of substituted phthalonitriles, see: Wö hrle et al (1993); Wu et al (1998); Li & Lieberman (2001); Sleven et al (2001); Li et al (2008); Seven et al (2009); Foo et al (2012). Table 1 Hydrogen-bond geometry (Å , ).…”

“…Phthalocyanine dyes can be made soluble in water and organic solvents by addition of suitable alkoxy or aryloxy groups (Jiang et al, 2011;Sleven et al, 2001). This is most easily achieved from the correspondingly substituted phthalonitriles which, in turn, are either prepared by Sandmeyer reaction of alkyl or alkoxy functionalized dihalobenzenes (Li & Lieberman, 2001;Sleven et al, 2001) or aryloxy / alkoxy displacement of the corresponding halophthalonitrile (Wöhrle et al, 1993;Li et al, 2008;Foo et al, 2012) or 4-nitrophthalonitrile (Wu et al, 1998;Seven et al, 2009). The latter method is most suitable for preparing 4-alkoxyphthalonitriles and was used for preparing the title compound, 4-(prop-2ylnyloxy)phthalonitrile (I).…”