Photoconvertible and Photoactivatable Perylene BisImide Based on Photocyclization

IF 8 2区材料科学 Q1 MATERIALS SCIENCE, MULTIDISCIPLINARY

Advanced Optical Materials Pub Date : 2024-09-24 DOI:10.1002/adom.202401511

Valentine Le Berruyer, Aurelie Perrier, Mayeul Collot

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Abstract

Photomodulable fluorophores constitute advanced materials as they possess the ability to modify their photophysical properties upon photoirradiation. A new mechanism of photoconversion is recently established, called Directed Photooxidation Induced Conversion based on the coupling of fluorophores with Aromatic Singlet oxygen Reactive Moieties (ASORMs). In this work, The Directed Photooxidation Induced Conversion (DPIC) mechanism is intended to be applied to Perylene BisImide (PBI) due to its appealing photophysical properties. The experimental results showed that coupling two ASORMs to the PBI core, here furan and pyrrole, led to impressive photomodulable fluorophores. While PBI-F exhibited a photoconversion of 100 nm shift, PBI-P displayed an 80-fold fluorescence intensity enhancement upon photoactivation. Analysis of the photoproducts showed that the conversion do not involve an addition of singlet oxygen on the ASORM. Instead, photoconversion occurred through efficient successive photocyclizations. Finally, intracellular vesicles are successfully photoconverted by means of endocytosed PLGA-polymer nanoparticles loaded with PBI-F. This study highlights the unique capability of furan- and pyrrole-conjugated fluorophores to enable advanced optical materials with phototransformation properties.

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基于光环化的可光电转换和光活化的亚珀尔二酰亚胺

可进行光调节的荧光团是一种先进的材料，因为它们具有在光照射下改变其光物理性质的能力。最近建立了一种新的光电转换机制，称为定向光氧化诱导转换（Directed Photooxidation Induced Conversion），其基础是荧光团与芳香族单线态氧活性分子（ASORMs）的耦合。在这项研究中，定向光氧化诱导转化（DPIC）机制因其具有吸引人的光物理特性而打算应用于二亚甲基双酰胺（PBI）。实验结果表明，将两种 ASORM（呋喃和吡咯）耦合到 PBI 核心上，可产生令人印象深刻的光调制荧光团。PBI-F 显示出 100 纳米位移的光电转换，而 PBI-P 则在光激活时显示出 80 倍的荧光强度增强。对光产物的分析表明，这种转换并不涉及在 ASORM 上添加单线态氧。相反，光转化是通过高效的连续光环化作用实现的。最后，通过内吞载入 PBI-F 的 PLGA 聚合物纳米颗粒，细胞内囊泡成功实现了光转化。这项研究凸显了呋喃和吡咯共轭荧光团的独特能力，使其成为具有光转化特性的先进光学材料。

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来源期刊

Advanced Optical Materials MATERIALS SCIENCE, MULTIDISCIPLINARY-OPTICS

CiteScore

13.70

自引率

6.70%

发文量

883

审稿时长

1.5 months

期刊介绍： Advanced Optical Materials, part of the esteemed Advanced portfolio, is a unique materials science journal concentrating on all facets of light-matter interactions. For over a decade, it has been the preferred optical materials journal for significant discoveries in photonics, plasmonics, metamaterials, and more. The Advanced portfolio from Wiley is a collection of globally respected, high-impact journals that disseminate the best science from established and emerging researchers, aiding them in fulfilling their mission and amplifying the reach of their scientific discoveries.