Polymer dimethyl silicone doped with crown functionalized tetraphenylethene macrocycle: A high selection discriminating film for benzene derivatives

A new class of crown functionalized TPE macrocycles were concisely synthesized. Furthermore, the 13 membered macrocycle 2O-1 exhibited changes in mechanofluorochromism (MFC) behaviors which could be rapidly self-reversible within 310 s at room temperature. These crown functionalized TPE macrocycles can be used as portable detection tools by doping into polymer dimethyl silicone (PDMS) film. Interestingly, the 1O-2 macrocycle film could efficient discriminate benzene from volatile organic compounds through visually fascinating emission color switching from blue to green-yellow. Notably, iodobenzene was different from other halogen benzene (F, Cl, Br), accompanying visibly discernible emission color switching from blue to dark-brown on 1O-2 macrocycle film. Thus, such macrocycle film will be applied as high selection discriminating test strip of benzene derivatives. Crown functionalized 13 membered TPE macrocycle with spontaneous reversed MFC behaviors within 310 s at room temperature. Interestingly, the macrocycle 1O-2 doped PDMS luminescent films display efficient discriminate character for benzene derivatives. Notably, iodobenzene was firstly found to be simply distinguished from other halogen benzene (F, Cl, Br) with conspicuous emission color switching from blue to dark-brown on the 1O-2 doped PDMS luminescent films. [Display omitted] •A novel class of 13-32 membered macrocycles were synthesized by intramolecular or intermolecular cyclization.•The PDMS film of 1O-2 could distinguish benzene from volatile organic compounds accompanying emission color switch.•Iodobenzene could be discriminated from other halogen benzene (F, Cl, Br) on macrocycle 1O-2 film.