title: Crystal structures of bis-(phen-oxy)silicon phthalocyanines: increasing π-π inter-actions, solubility and disorder and no halogen bonding observed.
abstract: We report the syntheses and characterization of three solution-processable phen-oxy silicon phthalocyanines (SiPcs), namely bis-(3-methyl-phen-oxy)(phthalocyanine)silicon [(3MP)2-SiPc], C46H30N8O2Si, bis-(2-sec-butyl-phen-oxy)(phthalocyanine)silicon [(2secBP)2-SiPc], C44H24I2N8O2Si, and bis-(3-iodo-phen-oxy)(phthalocyanine)silicon [(3IP)2-SiPc], C52H42N8O2Si. Crystals grown of these compounds were characterized by single-crystal X-ray diffraction and the π-π inter-actions between the aromatic SiPc cores were studied. It was determined that (3MP)2-SiPc has similar inter-actions to previously reported bis-(3,4,5-tri-fluoro-phen-oxy)silicon phthalocyanines [(345 F)2-SiPc] with significant π-π inter-actions between the SiPc groups. (3IP)2-SiPc and (2secBP)2-SiPc both experienced a parallel stacking of two of the peripheral aromatic groups. In all three cases, the solubility of these mol-ecules was increased by the addition of phen-oxy groups while maintaining π-π inter-actions between the aromatic SiPc groups. The solubility of (2secBP)2-SiPc was significantly higher than other bis-phen-oxy-SiPcs and this was exemplified by the higher observed disorder within the crystal structure.
authors.affiliation: University of Toronto, Department of Chemical Engineering & Applied Chemistry, 200 College Street, Toronto, Ontario, M5S 3E5, Canada; University of Ottawa, Department of Chemical and Biological Engineering, 161 Louis Pasteur, Ottawa, Ontario, K1N 6N5, Canada.
authors.forename: Benoît H
authors.initials: BH
authors.lastname: Lessard
authors.affiliation: University of Toronto, Department of Chemistry, 80 St. George Street, Toronto, Ontario, M5S 3H6, Canada.
authors.forename: Alan J
authors.initials: AJ
authors.lastname: Lough
authors.affiliation: University of Toronto, Department of Chemical Engineering & Applied Chemistry, 200 College Street, Toronto, Ontario, M5S 3E5, Canada; University of Toronto, Department of Materials Science and Engineering, 200 College Street, Toronto, Ontario, M5S 3E5, Canada; University of Toronto, Department of Chemistry, 80 St. George Street, Toronto, Ontario, M5S 3H6, Canada.
authors.forename: Timothy P
authors.initials: TP
authors.lastname: Bender
keywords: bonds; crystal structure; halogen; inter­actions; phenol; phen­oxy; phen­oxy­lation; phthalocyanine; silicon