Abstract
Tetraphenylethylene (TPE), a typical luminogen with aggregation-induced emission (AIE) features, has been widely used to prepare AIE fluorescent materials. In this study, TPE-functionalized polydimethylsiloxane (n-TPE-AP-PDMS) was successfully synthesized by attaching TPE to polydimethylsiloxane via aza-Michael addition. The introduction of polydimethylsiloxane to TPE had no obvious effect on photophysical properties. Intriguingly, n-TPE-AP-PDMS exhibited two opposite fluorescence emission behaviors in different systems: aggregation-induced quenching (ACQ) behavior in a tetrahydrofuran/water mixture and typical AIE phenomenon in a tetrahydrofuran/hexane mixture. This unexpected transition from ACQ to AIE can be attributed to a twisted intramolecular charge-transfer effect and flexible aminopropyl polydimethylsiloxane. n-TPE-AP-PDMS was further used as a fluorescent probe to detect nitrobenzene and it showed high quenching efficiency. Moreover, the n-TPE-AP-PDMS film showed high reversibility so that the quenching efficiency remained constant after five cycles. This work can provide a deeper understanding of AIE behavior and guidance to develop a new AIE polymer for chemosensors with high performance.
Highlights
Fluorescent materials have attracted much attention due to their fundamental and indispensable roles in human society
Synthesis and Characterizations n-TPE was attached to AP-PDMS polymer chains via aza-Michael addition reaction and the synthetic process were shown in Scheme 1
We demonstrated the synthesis of an Aggregation-induced emission (AIE) silicone polymer (n-TPEAP-PDMS) based on tetraphenylethylene via aza-Michael reaction
Summary
Fluorescent materials have attracted much attention due to their fundamental and indispensable roles in human society. Restriction of the intramolecular rotation (RIR) mechanism is considered to be primarily responsible for the AIE phenomenon Due to their excellent fluorescent properties, AIE luminogens have been extensively applied in various fields, including bioassay [3], membrane imaging [4], explosive detection [5], light-emitting diodes (OLEDs) [6] and liquid crystal materials [7]. Fluorescent polymers with flexible design of molecular structure and morphology as well as high thermal stability are ideal candidates to develop new AIE systems. The organic reaction to attach TPE moiety on the polymer skeletons becomes the key role to efficiently prepare AIE polymer He and coworkers [14] reported a spontaneous aza-Michael addition polymerization for efficient preparation of poly(enamine)s, which could proceed with 100% atom efficiency under mild conditions without any external catalyst. Investigation of the fluorescence-quenching behavior indicated that n-TPE-AP-PDMS film had detection sensitivity as well as good reversibility
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