American Chemical Society
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Versatile Strategy To Access Fully Functionalized Benzodifurans: Redox-Active Chromophores for the Construction of Extended π-Conjugated Materials

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posted on 2010-05-21, 00:00 authored by Chenyi Yi, Carmen Blum, Mario Lehmann, Stephan Keller, Shi-Xia Liu, Gabriela Frei, Antonia Neels, Jürg Hauser, Stefan Schürch, Silvio Decurtins
An efficient synthetic approach to construct a fully substituted benzo[1,2-b:4,5-b′]difuran (BDF) 2a via base-catalyzed double annulations is presented. Compound 2a can readily undergo Suzuki, Heck, and Sonogashira coupling reactions to afford in good yields a manifold of extended π-conjugated BDF derivatives, e.g., with pyridine termini (46) and with different spacers. These are highly luminescent materials that undergo two reversible one-electron oxidations. Remarkably, their photophysical and electrochemical properties can be largely tuned by methylation or protonation. Consequently, they can function as pH-dependent fluorescence switches. Finally, the observed electronic properties are explained on the basis of density functional theory.