Synthesis of dihydroxy silicon phthalocyanine tetrasulfonic acid and poly-μ-oxo silicon phthalocyanine tetrasulfonic acid

Abstract

ABSTRACT:We describe the synthesis of tetrasulfonated silicon phthalocyanine and its oligomer product prepared by metal salt catalyzed polycondensation. The catalytic effect of H 2 O-free CaCl 2 in quinoline is used for the polycondensation of dihydroxy silicon phthalocyanine to the cofacially arrayed oligomer. Spectroscopic characterization and photoelectron spectroscopy data of the prepared compounds are reported. We present the first results on polypyrrole films doped with these substances.

Silicon phthalocyanines: synthesis and resurgent applications

“…Direct reaction of the aromatic rings in SiPc. By means of a direct reaction, the aromatic rings of SiPc can be sulphonated, 66,67 to obtain enhanced photostability as well as aqueous solubility. In a typical reaction, 1 was heated with excess chlorosulphonic acid (ClSO3H) at 130 °C for 5 h and then cooled to 85 °C.…”

“…Thionyl chloride (30-fold excess) was slowly added to the solution and the reaction was continued for another 4 h. The resulting sulphonyl chloride SiPc adduct was isolated in pure form (yield ~68%) and then hydrolysed in methanol-water (1:5 v/v mixture) under reflux conditions for 3 h to obtain the tetrasulphonated SiPc, 15 in high reaction yields of ~87% (Scheme 9). 67 Importantly, the varying degrees of sulphonation depend on the SiPc:ClSO3H molar ratio and thus can be controlled. For example, use of SiPc and ClSO3H in 1:4 molar ratio resulted in isomeric mixtures of α or β substituted ( Fig.…”

Dual effect of light and ultrasound for efficient singlet oxygen generation with novel diaxial silicon phthalocyanine sensitizer

“…Also the aromatic C=N, C=C, C–C and C–N were seen at 1609, 1532, 1429 and 1334 cm −1 , respectively. The formation of the O–Si–O bond was validated by the significant vibrations observed at 1078 and 829 cm −1 27 . Moreover, the successful synthesis of the targeted molecule structure was confirmed by the appearance of characteristic vibrations of Si–O–C at 1233 and 978 cm −1 28 …”

“…The formation of the O-Si-O bond was validated by the significant vibrations observed at 1078 and 829 cm −1 . 27 Moreover, the successful synthesis of the targeted molecule structure was confirmed by the appearance of characteristic vibrations of Si-O-C at 1233 and 978 cm −1 . 28 SiPc structure was positively correlated with 1 H NMR spectrum.…”