Conformationally Confined Emissive Cationic Macrocycle with Photocontrolled Organelle‐Specific Translocation

Abstract

The optimization of molecular conformation and aggregation modes is of great significance in creation of new luminescent materials for biochemical research and medical diagnostics. Herein, a highly emissive macrocycle ( 1 ) is reported, which is constructed by the cyclization reaction of triphenylamine with benzyl bromide and exhibits very distinctive photophysical performance both in aqueous solution and the solid state. Structural analysis reveals that the 1 can form self‐interpenetrated complex and emit bright yellow fluorescence in the crystal lattice. The distorted yet symmetrical structure can endow 1 with unique two‐photon absorption property upon excitation by near‐infrared light. Also, 1 can be utilized as an efficient photosensitizer to produce singlet oxygen ( 1 O 2 ) both in inanimate milieu and under cellular environment. More intriguingly, due to the strong association of 1 with negatively charged biomacromolecules, organelle‐specific migration is achieved from lysosome to nucleus during the 1 O 2 ‐induced cell apoptosis process. To be envisaged, this conformationally confined cationic macrocycle with photocontrolled lysosome‐to‐nucleus translocation may provide a feasible approach for in situ identifying different biospecies and monitoring physiological events at subcellular level.

Light-Driven Mitochondrion-to-Nucleus DNA Cascade Fluorescence Imaging and Enhanced Cancer Cell Photoablation

“…Consequently, the migration process of SPP appears to be independent of MMP. Furthermore, it has also been reported that some molecules migrated from mitochondria or lysosomes to nuclei by generating ROS and damaging the organelles under light irradiation. − To confirm the ROS generation of SPP in living cells, 2′,7′-dichlorofluorescin diacetate was used as the indicator. As illustrated in Figure S43, no significant fluorescence was observed during the migration process upon light irradiation, which indicates that SPP cannot generate ROS in living cells under light conditions.…”

A Photosensitive Cationic Macrocycle Based on Triphenylamine as Photocatalysts for Selective Photooxidation of Phosphines, Styrenes, and Hydroazobenzenes

“…The detailed process for synthesizing TPPB could be obtained from Supporting Information, Scheme S1. 54 Compound A (238 mg, 0.5 mmol) and 1,4-bis(bromomethyl)benzene (132 mg, 0.5 mmol) were dissolved in 20 mL of CH 3 CN and refluxed for 3 days under the N 2 at 95 °C. The reaction mixture was then cooled to room temperature and filtered.…”

A novel photoswitchable AIE-active supramolecular photosensitizer with synergistic enhancement of ROS-generation ability constructed by a two-step sequential FRET process

“…Thus, PS-related nanomaterials with attractive AIE properties could serve as an ideal alternative for conventional PSs. 17–21 Additionally, Förster resonance energy transfer (FRET) is perceived as an efficient strategy for PSs to achieve various wave-bands through switchable energy transfer effects. 22–25 Therefore, the development of efficient supramolecular PSs that combine excellent AIE properties with photoswitchability based on host–guest interactions and the FRET process is highly appealing.…”