Comprehensive Summary Organic room‐temperature phosphorescence (RTP) materials have attracted immense attention in bioimaging due to their long emission lifetime and large Stokes shift. RTP materials with long emission wavelength can improve the penetration depth for bioimaging. However, the design of red persistent RTP materials is still challenging. In this study, a fused‐ring structure has been proposed to effectively decrease the triplet energy level, thus extending the emission wavelength of phosphorescence. In addition, the fused‐ring structure exhibits a high molar extinction coefficient (ɛ) and high luminescence efficiency due to the rigid structure. A new class of crystalline hosts (iminodibenzyl, IDB) are developed to stabilize the triplet excitons that are generated from the fused‐ring molecules. The maximum RTP wavelength of doping materials can reach 635 nm with a lifetime of 9.35 ms. Water‐disperse nanoparticles are successfully prepared for in vivo time‐resolved bioimaging, which eliminates the background fluorescence interference from biological tissues. These reveal a delicate design strategy for the construction of long‐wavelength emissive RTP materials for high‐resolution bioimaging.

Photodynamic immunotherapy is a promising treatment strategy that destroys primary tumors and inhibits the metastasis and relapse of distant tumors. As reactive oxygen species are an intermediary for triggering immune responses, photosensitizers (PSs) that can actively target and efficiently trigger oxidative stress are urgently required. Herein, pyrrolo[3,2‐b]pyrrole as an electronic donor is introduced in acceptor–donor–acceptor skeleton PSs (TP‐IS1 and TP‐IS2) with aggregation‐induced emission properties and high absorptivity. Meanwhile, pyrrolo[3,2‐b]pyrrole derivatives innovatively prove their ability of type I photoreaction, indicating their promising hypoxia‐tolerant advantages. Moreover, M1 macrophages depicting an ultrafast delivery through the cell‐to‐cell tunneling nanotube pathway emerge to construct TP‐IS1@M1 by coating the photosensitizer TP‐IS1. Under low concentration of TP‐IS1@M1, an effective immune response of TP‐IS1@M1 is demonstrated by releasing damage‐associated molecular patterns, maturating dendritic cells, and vanishing the distant tumor. These findings reveal insights into developing hypoxia‐tolerant PSs and an efficient delivery method with unprecedented performance against tumor metastasis.

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The cell membrane protects the cell stability and balance and participates in various physiological activities as an exchange channel. Therefore, the real-time monitoring of cell membrane biological dynamics can help us understand the physiological state of the current cell. Herein, a type of amphiphilic near infrared (NIR) aggregation-induced emission (AIE) molecules was designed and synthesized. Multiarylpyrroles (MAPs) with a dodecyl chain at the 1-position of the pyrrole ring, charged pyridinium sulfonate at the 2,5-position of the pyrrole ring and free rotating aryls at the 3-position of the pyrrole ring can target cell membranes. One of the MAPs, MAP22, had a maximum emission wavelength in the aggregation state of up to 721 nm with a large Stokes shift (2 80 nm). In addition, MAP22 nanoparticles can produce reactive oxygen species (ROS) with a quantum yield of 224%. Therefore, these AIE MAPs are promising candidates for theranostic nanoagents, including NIR fluorescence imaging to target cell membranes and ablate cancer cells by producing ROS.