A tetraphenylethene-based hexacationic molecular cage with an open cavity

Cao, Fan; Duan, Honghong; Li, Qingfang; Cao, Liping

doi:10.1039/d2cc05153b

Cited by 3 publications

(1 citation statement)

References 34 publications

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“…[10,21,22,24,25] However, the nature of reversibility may also have stability issues. On the other hand, organic cages with TPE and TBPE building blocks have been formed by irreversible bond-forming reactions, such as S N Ar, [9] nucleophilic substitution with pyridine, [26,27] and thiol-Michael addition. [28] However, these reactions face challenges due to low yields and challenging synthetic and purification conditions.…”

Section: Introductionmentioning

confidence: 99%

Emissive Click Cages

Maji,

Samanta,

Samanta

et al. 2023

Chemistry A European J

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Herein, we report the synthesis of cofacial organic cage molecules containing aggregation‐induced emissive (AIE) luminogens (AIEgens) through four‐fold Cu(I)‐catalyzed azide‐alkyne cycloaddition (CuAAC) “click” reactions. The shorter AIEgen tetraphenylethylene (TPE) afforded two orientational isomers. The longer building blocks of tetrabiphenylethylene (TBPE) afforded a single isomer. The click reaction employed is irreversible, yet it yields remarkable four‐fold click products above 40%. The phenyl rings around the ethylene core generate propeller‐shaped chirality owing to their orientation, which influences the chirality of the resulting cages. The shorter cages are a mixture of PP/MM isomers, while the longer ones are a mixture of PM/MP isomers, at least in the solid state. The newly synthesized cage molecules were emissive even in dilute solutions (THF) and exhibited enhanced AIE upon the addition of water. Upon aggregation in aqueous solution, the organic cage molecules exhibit turn‐off emission sensing of nitroaromatic explosives with selectivity for picric acid in 25‐38 nanomolar detection range.

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