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Abstract
Bis(piperidyl)anthracenes were developed as structurally simple, bright and colour tuneable AIE luminogens and their emission mechanisms were analysed.
Highlights
Aggregation-induced emission (AIE) luminogens have found many applications, in organic light-emitting diodes (OLEDs),[8,9] and in environmentresponsive fluorescent probes,[1,10] which are sensitive to aggregation and self-assembly
We report the synthesis of various regioisomers of piperidylanthracenes (PAs) and bis(piperidyl)anthracenes (BPAs), and we discuss the effect of regioisomerism on their solid-state fluorescence properties (Chart 2)
Our results revealed that only 1,4-BPA and 9,10-BPA exhibit AIE behaviour, and that their fluorescence colours are tuneable without the introduction of additional substituents (Chart 1)
Summary
The effect of regioisomerism on the solid-state fluorescence of bis(piperidyl)anthracenes: structurally simple but bright AIE luminogens†. Aggregation-induced emission (AIE) was observed only for 1,4-BPA and 9,10-BPA, in which two piperidyl groups are substituted at the anthracene moiety in the para-position with respect to each other. Compared to previously reported AIE luminogens, these obtainable para-substituted BPAs, exhibited several unique and beneficial features, such as simple structures, bright solid-state fluorescence (Ffl = 0.49 and 0.86 for 1,4-BPA and 9,10-BPA, respectively), tunable fluorescence emission, and large Stokes shifts. The X-ray crystallographic analysis of 1,4-BPA revealed that undesirable interchromophoric interactions can be minimised, while TD-DFT calculations suggested that the enhanced Stokes shift of 1,4-BPA arises from severe electronic repulsion between neighbouring piperidyl moieties, which presumably results in the absence of self-absorption
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