Crystal structures of bis­(phen­oxy)silicon phthalocyanines: increasing π–π inter­actions, solubility and disorder and no halogen bonding observed

Acta Crystallographica Section E: Crystallographic Communications

Lough, A.J.¹  Bender, T.P.²  Lessard, B.H.³ 

[1] 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;University of Toronto, Department of Chemical Engineering &University of Toronto, Department of Chemistry, 80 St. George Street, Toronto, Ontario, M5S 3H6, Canada

关键词: CRYSTAL STRUCTURE;    SILICON;    PHTHALOCYANINE;    PHENOL;    PHENOXY;    PHENOXYLATION;    INTERACTIONS;    HALOGEN;    BONDS;   

DOI  :  10.1107/S205698901600935X

学科分类：数学（综合）

来源: International Union of Crystallography

【 摘 要 】

We report the syntheses and characterization of three solution-processable phen­oxy silicon phthalocyanines (SiPcs), namely bis­(3-methyl­phen­oxy)(phthalocyanine)silicon [(3MP)2-SiPc], C46H30N8O2Si, bis­(2-sec-butyl­phen­oxy)(phthalocyanine)silicon [(2secBP)2-SiPc], C44H24I2N8O2Si, and bis­(3-iodo­phen­oxy)(phthalocyanine)silicon [(3IP)2-SiPc], C52H42N8O2Si. Crystals grown of these compounds were characterized by single-crystal X-ray diffraction and the π–π inter­actions between the aromatic SiPc cores were studied. It was determined that (3MP)2-SiPc has similar inter­actions to previously reported bis­(3,4,5-tri­fluoro­phen­oxy)silicon phthalocyanines [(345 F)2-SiPc] with significant π–π inter­actions 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 mol­ecules was increased by the addition of phen­oxy groups while maintaining π–π inter­actions between the aromatic SiPc groups. The solubility of (2secBP)2-SiPc was significantly higher than other bis-phen­oxy-SiPcs and this was exemplified by the higher observed disorder within the crystal structure.

【 授权许可】

CC BY