Synthesis of Unsymmetrically Substituted Subphthalocyanines

✍ Scribed by Christian G. Claessens; Tomás Torres

• Publisher: John Wiley and Sons
• Year: 2000
• Tongue: English
• Weight: 203 KB
• Volume: 6
• Category: Article
• ISSN: 0947-6539
• DOI: 10.1002/1521-3765(20000616)6:12<2168::aid-chem2168>3.0.co;2-n

✦ Synopsis

A series of new unsymmetrically substituted subphthalocyanines containing iodo or octylthioether substituents on the outer aromatic rings have been synthesized. The statistical reaction of one equivalent of 1,2-dicyano-3-iodobenzene whether with two equivalents of 1,2-dicyano-4-octylthiobenzene or with two equivalents of 1,2dicyano-4,5-dioctylthiobenzene in the presence of boron trichloride in 1chloronaphthalene yielded in both cases all the possible expected unsymmetrically substituted subphthalocyanines, which were separated by column chro-matography on silica gel. All compounds were identified by FAB mass spectrometry and then characterized by HR-LSIMS spectrometry. The unambiguous characterization of each constitutional isomer was made possible by careful examination of the symmetry environment experienced by each proton on their 1 H-NMR spectra.