Silyl- and Disilanyl-BODIPYs: Synthesis via Catalytic Dehalosilylation and Spectroscopic Properties
Sisi Wang1, Hua Lu1, Yanping Wu1
1Key Laboratory of Organosilicon Chemistry and Material Technology, Ministry of Education, Hangzhou Normal University, Hangzhou, 310012, China.
Abstract:
We describe herein the first synthesis of silyl- and disilanyl-BODIPYs through transition-metal-catalyzed dehalosilylation of iodo-BODIPYs using a Pd(P(tBu)3 )2 /Et3 N/toluene system. Various mono- and bis-silyl-BODIPYs, mono- and bis-disilanyl-BODIPYs and bis-BODIPYs linked by silylene and SiOSi groups were synthesized by using this straightforward method. Silyl- and disilanyl-substitution significantly modifies the spectroscopic properties of the BODIPY, in which the fluorescence quantum yields of the silyl-BODIPYs are remarkably increased, whereas the emission spectra of disilanyl-BODIPYs are red-shifted due to effective σ(SiSi)-π(BODIPY) conjugation.
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