Synthesis and properties of the silicon phthalocyanines with two axial fullerene substituents

ORGN 424

Dong Jin Kim, Kwang-Yol Kay, and Eui Su Kang. Department of Molecular Science and Technology, Ajou University, Suwon, 442-749, South Korea
Fullerene-functionalized phthalocyanines (Pcs) are rare and no Pc with more than one fullerene substituent has been reported so far. We report here the first synthesis of the soluble Pcs 1 and 2 with two axial fullerene substituents as well as different distances between Pc core and fullerene. These Pcs were prepared by reaction of silicon phthalocyanine dichloride with bis-adducts of C60 bearing a phenol (for 1) or an alcohol (for 2) functionality in the presence of base. The structure of 1 and 2 have been confirmed by 1H-NMR, 13C-NMR, FT-IR and MALDI-TOF Ms. Comparison of line-width studies in UV/Vis spectra of the solution and the spin-coated films of 1 and 2 together with the results from polarized optical microscopy (POM), atomic force microscopy (AFM) and differential scanning calorimeter (DSC) showed that Pcs 1 and 2 with two axial fullerene substituents produce transparent glassy solids. Redox waves were observed and compared in both negative and positive potential regions by cyclic voltammetry (CV) and differential pulsed voltammetry (DPV), showing charge transfer phenomena between Pc ring and fullerene in both compounds 1 and 2.

 

Physical Organic, Materials, Heterocycles, Aromatics, Metal-Mediated Reactions
8:00 PM-10:00 PM, Tuesday, September 9, 2003 Hilton New York -- Americas Hall 1, Poster

Division of Organic Chemistry
The 226th ACS National Meeting, New York, NY, September 7-11, 2003