Max Planck Institute for Polymer Research, Ackermannweg 10, Mainz 55128, Germany.
Department of Chemistry, Johannes Gutenberg-University, Mainz 55099, Germany.
J Am Chem Soc. 2023 Dec 6;145(48):26487-26493. doi: 10.1021/jacs.3c11314. Epub 2023 Nov 27.
A terrylenedicarboximide-anthraquinone dyad, , with absorption in the second near-infrared region (NIR-II) is obtained as a high-performance chromophore for photothermal therapy (PTT). The synthetic route proceeds by C-N coupling of amino-substituted terrylenedicarboximide (TMI) and 1,4-dichloroanthraquinone followed by alkaline-promoted dehydrocyclization. with extended π-conjugation exhibits an optical absorption band peaking at 1140 nm and extending into the 1500 nm range. Moreover, as determined by dielectric spectroscopy in dilute solutions, achieves an ultrastrong dipole moment of 14.4 ± 0.4 Debye due to intense intramolecular charge transfer. After encapsulation in a biodegradable polyethylene glycol (DSPE-mPEG2000), nanoparticles (NPs) deliver a high photothermal conversion efficiency of 49% under 1064 nm laser irradiation combined with excellent biocompatibility, photostability, and photoacoustic imaging capability. and studies reveal the great potential of NPs in photoacoustic-imaging-guided photothermal therapy for orthotopic liver cancer treatment in the NIR-II window.
一种苝二酰亚胺-蒽醌二聚体 ，在近红外二区（NIR-II）有吸收，作为光热治疗（PTT）的高性能发色团。该合成路线通过氨基取代的苝二酰亚胺（TMI）和 1,4-二氯蒽醌的 C-N 偶联，然后在碱性条件下促进脱氢环化进行。具有扩展的 π 共轭的 ，在 1140nm 处出现峰值，并延伸到 1500nm 范围。此外，通过在稀溶液中的介电光谱测定， 由于强烈的分子内电荷转移，实现了 14.4±0.4 德拜的超强偶极矩。在可生物降解的聚乙二醇（DSPE-mPEG2000）中封装后， 在 1064nm 激光照射下，光热转换效率高达 49%，同时具有良好的生物相容性、光稳定性和光声成像能力。 研究表明，在 NIR-II 窗口中， NPs 在光声成像引导光热治疗原位肝癌治疗中具有巨大的潜力。
