Heavy-atom-free BODIPY photosensitizers with intersystem crossing mediated by intramolecular photoinduced electron transfer.,Organic & Biomolecular Chemistry

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Heavy-atom-free BODIPY photosensitizers with intersystem crossing mediated by intramolecular photoinduced electron transfer.
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2019-11-12 , DOI: 10.1039/c9ob02170a
Mikhail A Filatov ₁

Affiliation

Organic photosensitizers possessing efficient intersystem crossing (ISC) and forming long-living triplet excited states, play a crucial role in a number of applications. A common approach in the design of such dyes relies on the introduction of heavy atoms (e.g. transition metals or halogens) into the structure, which promote ISC via spin–orbit coupling interaction. In recent years, alternative methods to enhance ISC have been actively studied. Among those, the generation of triplet excited states through photoinduced electron transfer (PET) in heavy-atom-free molecules has attracted particular attention because it allows for the development of photosensitizers with programmed triplet state and fluorescence quantum yields. Due to their synthetic accessibility and tunability of optical properties, boron dipyrromethenes (BODIPYs) are so far the most perspective class of photosensitizers operating via this mechanism. This article reviews recently reported heavy-atom-free BODIPY donor–acceptor dyads and dimers which produce long-living triplet excited states and generate singlet oxygen. Structural factors which affect PET and concomitant triplet state formation in these molecules are discussed and the reported data on triplet state yields and singlet oxygen generation quantum yields in various solvents are summarized. Finally, examples of recent applications of these systems are highlighted.

中文翻译：

无重原子的BODIPY光敏剂，具有分子间光诱导的电子转移介导的系统间交叉。

具有有效的系统间交叉（ISC）并形成长寿命三线态激发态的有机光敏剂在许多应用中都起着至关重要的作用。设计此类染料的常用方法是将重原子（例如过渡金属或卤素）引入结构中，从而通过以下途径促进ISC：自旋-轨道耦合相互作用。近年来，已经积极研究了增强ISC的替代方法。其中，通过无重原子分子中的光致电子转移（PET）产生三重激发态引起了人们的特别关注，因为它允许开发具有程序化三重态和荧光量子产率的光敏剂。由于它们的合成可及性和光学性能的可调节性，硼二吡咯烷酮（BODIPYs）迄今为止是通过这种机制。本文回顾了最近报道的无重原子的BODIPY供体-受体二聚体和二聚体，它们产生长寿命的三重态激发态并产生单线态氧。讨论了影响这些分子中PET和伴随的三重态形成的结构因素，并总结了各种溶剂中三重态产率和单重态氧生成量子产率的报道数据。最后，重点介绍了这些系统的最新应用示例。

更新日期：2019-11-12

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