Synthesis, conformational control, and photothermal application of helically twisted 3,6-carbazole-based porphyrinoids and mono-palladium complex

Chengming Li, Weihua Zhuang, Yongjie Zhou, Linfeng He, Jiayin Yang (), Gang Xu, Rongchuan Su, Mao Chen () and Jingsong You ()
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Chengming Li: Sichuan University
Weihua Zhuang: Sichuan University
Yongjie Zhou: Sichuan University
Linfeng He: Sichuan University
Jiayin Yang: Sichuan University
Gang Xu: Sichuan University
Rongchuan Su: North Sichuan Medical College
Mao Chen: Sichuan University
Jingsong You: Sichuan University

Nature Communications, 2025, vol. 16, issue 1, 1-14

Abstract: Abstract Synthetic control over multiple conformations of expanded porphyrinoids, which are intrinsically linked to their properties and functions, has long been a key objective in chemical research. Here, we present an N-substituent-controlled synthesis of 3,6-carbazole-based octaphyrins and dodecaphyrins via modified Rothemund-type condensation. The choice of pre-modified N-substituents (hydrogen, methyl, tert-butoxycarbonyl) on the 3,6-carbazolylene precursors critically dictates the assembly pathway, enabling access to porphyrinoids with distinct conformations. The octaphyrin scaffold comprises two figure-eight geometries and a half-twisted Möbius form, shaped by solvent-drived kinetic and thermodynamic control. The dodecaphyrins display two helically twisted topologies governed by thermodynamical control. Metalation with Pd(OAc)₂ stabilizes the dynamic twist of octaphyrin into a specific figure-eight geometry, yielding a mono-PdII complex featuring an unconventional NNCC–Pd coordination mode. All these systems exhibit pronounced optical responses to near-infrared light and the mono-PdII complex demonstrates efficient photothermal conversion after encapsulation within nanoparticles, allowing for tumor phototheranostics in the near-infrared bio-window.

Date: 2025
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DOI: 10.1038/s41467-025-62763-1

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