Abstract
AbstractA novel synthetic strategy gives reversible cross‐linked polymeric materials with tunable fluorescence properties. Dimaleimide‐substituted tetraphenylethene (TPE‐2MI), which is non‐emissive owing to the photo‐induced electron transfer (PET) between maleimide (MI) and tetraphenylethene (TPE) groups, was used to cross‐link random copolymers of methyl (MM), decyl (DM) or lauryl (LM) methacrylate with furfuryl methacrylate (FM). The mixture of copolymer and TPE‐2MI in DMF showed reversible fluorescence with “on/off” behavior depending on the Diels–Alder (DA)/retro‐DA process, which is easily adjusted by temperature. At high temperatures, the retro‐DA reaction is dominant, and the fluorescence is quenched by the photo‐induced electron transfer (PET) mechanism. In contrast, at low temperatures, the emission recovers as the DA reaction takes over. A transparent PMFM/TPE‐2MI polymer film was prepared which shows an accurate response to the external temperature and exhibited tunable fluorescent “turn on/off” behavior. These results suggest the possible application in areas including information security and transmission. An example of invisible/visible writing is given.
Highlights
Cross-linked materials have played an important role in many areas such as coatings, adhesives, composite materials, and biomaterials
A plethora of efforts has been made to expand the application of reversibly cross-linked materials in many areas, [10] while there are very few in the field of reversible/tunable fluorescence
The aggregationinduced emission (AIE) behavior of TPE2AFM was confirmed by the investigation of its THF/H2O solutions, and the results were shown in Figure S6 (SI)
Summary
Cross-linked materials (thermosets) have played an important role in many areas such as coatings, adhesives, composite materials, and biomaterials. The breakage of PET process by reaction of TPE-2MI with furan moieties releases the AIE behavior, and the cross-linked networks restricts the mobility of TPE molecules to enhance their emission. This phenomenon, of the reversible crosslinking-induced-emission, has not been reported so far. By using this method, it is possible to regulate the emission of cross-linked materials by reversible covalent chemistry. The obtained TPE-2MI and furfuryl methacrylate were confirmed by the 1H NMR spectrum (Figure S2b, SI) These results show efficient DA and retro-DA reaction between TPE-2MI and furfuryl methacrylate under different temperatures.
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