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Silyl‐ and Disilanyl‐BODIPYs: Synthesis via Catalytic Dehalosilylation and Spectroscopic Properties
Author(s) -
Wang Sisi,
Lu Hua,
Wu Yanping,
Xiao Xuqiong,
Li Zhifang,
Kira Mitsuo,
Shen Zhen
Publication year - 2017
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201601637
Subject(s) - silylation , bodipy , silylene , chemistry , toluene , photochemistry , catalysis , fluorescence , rhodium , combinatorial chemistry , organic chemistry , silicon , physics , quantum mechanics
Abstract We describe herein the first synthesis of silyl‐ and disilanyl‐BODIPYs through transition‐metal‐catalyzed dehalosilylation of iodo‐BODIPYs using a Pd(P( t Bu) 3 ) 2 /Et 3 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.