Synthesis and property of novel phthalocyanine having a 3,5-bis-pentafluorosulfanylphenyl group on the α-peripheral position

• Phthalocyanine having Ph(SF5)2 group on α-position was synthesized.
• The effect of SF5 on phthalocyanine was investigated by comparison with CF3 analogue.
• The SF5 moiety inhibits protonation of the phthalocyanine, while CF3 does not.
• Bulky SF5 group can control dihedral angle of the phenyl plane of phthalocyanine.

The pentafluorosulfanyl (SF5) group is bulky, highly lipophilic, highly electronegative, and highly stable. Despite the potential use of SF5-containing phthalocyanines, no example exists. We herein report the synthesis of 3,5-bis-pentafluorosulfanylphenyl ((SF5)2Ph)-substituted phthalocyanine onto the α-peripheral position for the first time. Regioselective synthesis was possible by the effect of the SF5 moiety via macrocyclization. The synthesis of phthalocyanines with CF3 and H instead of SF5 was also carried out in order to investigate the effect of SF5. Phthalocyanines were compared using UV/Vis spectra. Phthalocyanine with SF5 exists free from aggregation and protonation in dichloromethane solution. The two planes of 3,5-(SF5)2Ph and parent Pc ring in space are nearly perpendicular at which they meet is a right angle, while the two planes of CF3 analogue in space are not.

The synthesis of 3,5-bis-pentafluorosulfanylphenyl ((SF5)2Ph)-substituted phthalocyanine 2 is reported. Phthalocyanine 2 was designed to be robust and durable without losing its non-aggregation property. The optical property of 2 was investigated by comparing phthalocyanines 1 and 3 having phenyl or a 3,5-bis(trifluoromethyl)phenyl group on the α-peripheral position.Figure optionsDownload as PowerPoint slide