A Series of Singlet-Triplet InVerted TADF Fluorescent Probes with High Stability, Low Molecular Weight, and Synthesis Accessibility,Advanced Theory and Simulations

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A Series of Singlet-Triplet InVerted TADF Fluorescent Probes with High Stability, Low Molecular Weight, and Synthesis Accessibility
Advanced Theory and Simulations ( IF 2.9 ) Pub Date : 2023-03-02 , DOI: 10.1002/adts.202200863
Rongchuan Su ₁ , Zhenmei Huang ₂

Affiliation

Thermally activated delayed fluorescence (TADF)-based fluorescent biological probes embedded with near infrared (NIR) emission have some unique properties, such as minimal photodamage, low light scattering, and deep tissue penetration. Typical TADF materials are based on electron donors and acceptors, all of them have broad emission and high molecular weight, which is not ideal for biological applications. The cycl[3,3,3]azine is a multiple resonance effect (MRE)-like TADF fluorescent compound, with narrow NIR emission, inverted singlet-triplet gaps, and low molecular weight, which is an ideal platform for biological applications. However, the low stability of cycl[3,3,3]azine and its anti-Kasha's rule nature limit its biological applications. In this work, the authors have rationally investigated the decomposition process of cycl[3,3,3]azine, and a series of NIR and MRE-like molecules are designed. These molecules would be stable in the biological environment and NIR fluorescence can also be emitted from the first excited state, the synthesis route has also been proposed. In a word, this work provides a series of biological probes with inverted singlet-triplet gaps, good stability, and low molecular weight for further study.

中文翻译：

一系列具有高稳定性、低分子量和合成可及性的单重态-三重态倒置 TADF 荧光探针

嵌入近红外 (NIR) 发射的基于热激活延迟荧光 (TADF) 的荧光生物探针具有一些独特的特性，例如最小的光损伤、低光散射和深层组织穿透。典型的 TADF 材料基于电子供体和受体，它们都具有宽发射和高分子量，这对于生物应用来说并不理想。环[3,3,3]吖嗪是一种类多共振效应（MRE）的TADF荧光化合物，具有窄近红外发射、倒单三重态能隙、低分子量等特点，是生物应用的理想平台。然而，环[3,3,3]嗪的低稳定性及其抗卡沙规则性质限制了其生物学应用。在这项工作中，作者合理地研究了环[3,3,3]嗪的分解过程，并设计了一系列 NIR 和 MRE 类分子。这些分子在生物环境中很稳定，也可以从第一激发态发出近红外荧光，也提出了合成路线。总之，本工作为进一步研究提供了一系列具有倒置单三重态间隙、稳定性好、低分子量的生物探针。

更新日期：2023-03-02

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