Singlet oxygen (1O2) is a highly reactive species central to applications ranging from materials science to photodynamic therapy, yet its detection and controlled handling remain challenging. Herein, we report two new 4a,5a-dihydroazuleno[2,1,8-ija]azulene derivatives, T-AA-F and K-AA-F, uniquely integrate photosensitization, 1O2 capture, storage, and release within a single small-molecule scaffold. Upon UV or visible light irradiation, both compounds generate 1O2 and undergo a selective [4 + 2] cycloaddition at the fused furan unit to form stable endoperoxides exhibiting red emission. Prolonged irradiation using UV (365 nm) or visible light (525 nm) triggers a ring-opening reaction, regenerates the ketone derivatives while releasing 1O2, as confirmed by EPR spectroscopy using TEMP as a trapping agent. The endoperoxides display high thermal stability up to 90 °C, enabling robust 1O2 storage. This fully integrated molecular system represents a rare example of a single-component platform capable of producing, trapping, storing, and releasing 1O2, offering promising opportunities for sensing and bioimaging applications.

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A Sn-mediated mechanochemical reductive aromatization of 1,4-dihydroxy- and 1,4-dimethoxy-cyclohexadienes has been used to form 12 acenes, including derivatives of benzene, anthracene, tetracene, pent...

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The synthesis, electrochemical, spectroelectrochemical, photophysical and light induced electron transfer reactions in two new anthanthrene quinodimethanes have been studied and analyzed in the contex...

Herein, we report the use of alkyne benzannulation on zigzag-edged dibenzochrysene derivatives to extend the conjugation and reduce their bandgap. Unexpectedly, the ring closure reaction takes place ...