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

We report the syntheses and characterization of three solution-processable phen­oxy silicon phthalocyanines (SiPcs), namely bis­(3-methyl­phen­oxy)(phthalocyanine)silicon [(3MP)(2)-SiPc], C(46)H(30)N(8)O(2)Si, bis­(2-sec-butyl­phen­oxy)(phthalocyanine)silicon [(2secBP)(2)-SiPc], C(44)H(24)I(2)N(8)O(2)Si, and bis­(3-iodo­phen­oxy)(phthalocyanine)silicon [(3IP)(2)-SiPc], C(52)H(42)N(8)O(2)Si. 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.