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An efficient procedure has been researched for the solvent-free synthesis of bis(indolyl)methanes via a one-pot reaction of indoles and aldehydes or ketones promoted by PEG1000-based dicationic acidic ionic liquid (PEG1000-DAIL). The catalyst PEG1000-DAIL could be reused seven times with excellent results. Furthermore, through this method, a highly chemoselective reaction of benzaldehyde and acetophenone with indole could be achieved.