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Journal ArticleDOI

Strategic Construction of Sulfur-Bridged BODIPY Dimers and Oligomers as Heavy-Atom-Free Photosensitizers.

31 Aug 2021-Organic Letters (American Chemical Society (ACS))-Vol. 23, Iss: 18, pp 7220-7225
TL;DR: In this paper, an efficient strategy for building sulfur-bridged oligo-BODIPYs based on the SNAr reaction is described, which showed broadband and strong visible-near-infrared (NIR) light absorption, strong intramolecular exciton coupling, and efficient intersystem crossing.
About: This article is published in Organic Letters.The article was published on 2021-08-31. It has received 7 citations till now. The article focuses on the topics: Intersystem crossing & BODIPY.
Citations
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Journal ArticleDOI
TL;DR: In this article, a cyclic trimeric BODIPY array with a lifetime up to 257.5 μs was generated from easily accessible meso-mesityldipyrrinone and arylboronic acids in one pot.
Abstract: In photosensitizers, long triplet excited state lifetimes are key to their efficient electron transfer or energy transfer processes. Herein, we report a novel class of cyclic trimeric BODIPY arrays which were efficiently generated from easily accessible meso-mesityldipyrrinone and arylboronic acids in one pot. Arylboronic acid, for the first time, was used to provide a boron source for BODIPY derivatives. Due to the well-defined and orthogonally aligned BODIPY cores as verified by X-ray crystallography, these BODIPY arrays show strong exciton coupling effects and efficient intersystem crossings, and are novel heavy-atom-free photosensitizers with a long-lived triplet excited state (lifetime up to 257.5 μs) and good reactive oxygen species generation efficiency (up to 0.72) contributed by both 1O2 and O2−˙ under light irradiation.

20 citations

Journal ArticleDOI
TL;DR: In this article, a straightforward postmodification synthesis for a family of thiophene-fused BODIPY dimers and tetramers through transforming flexible sulfur bridges into coplanar Thiophene fusions was described.

6 citations

Journal ArticleDOI
TL;DR: In this article, a family of directly β,γ-linked BODIPY oligomers up to pentamers were regioselectively prepared via Pd(II)-catalyzed oxidative C-H cross-coupling.

5 citations

Journal ArticleDOI
TL;DR: Sulfoxide-bridged dimeric BODIPYs were developed as a new class of long-wavelength photoconvertible fluorophores in this paper , and the combination of photoactivation and red-shifted excitation/emission offered optimal contrast and eliminated the interference from biological autofluorescence.
Abstract: Sulfoxide-bridged dimeric BODIPYs were developed as a new class of long-wavelength photoconvertible fluorophores. Upon visible-light irradiation, a sulfoxide moiety was released to generate the corresponding α,α-directly linked dimeric BODIPYs. The extrusion of SO from sulfoxides was mainly through an intramolecular fashion involving reactive triplet states. By this photoconversion, not only were more than 100 nm red shifts of absorption and emission maxima (up to 648/714 nm) achieved but also stable products with bright fluorescence were produced with high efficiency. The combination of photoactivation and red-shifted excitation/emission offered optimal contrast and eliminated the interference from biological autofluorescence. More importantly, the in situ products of these visible-light-induced reactions demonstrated ideal single-molecule fluorescence properties in the near-infrared region. Therefore, this new photoconversion could be a powerful photoactivation method achieving super-resolution single-molecule localization imaging in a living cell without using UV illumination and cell-toxic additives.

4 citations

Journal ArticleDOI
TL;DR: In this article , the authors highlight the construction strategies, recognition mechanisms as well as biological imaging applications of various BODIPY-based hypoxia probes, and promote the development of diagnostics for tumors and hypoxyia-responsive anticancer nanomedicines.

3 citations

References
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Journal ArticleDOI
TL;DR: The Bodipy family, first developed as luminescent tags and laser dyes, has become a cornerstone for these new applications and the near future looks extremely bright for "porphyrin's little sister".
Abstract: The world of organic luminophores has been confined for a long time to fairly standard biological labeling applications and to certain analytical tests. Recently, however, the field has undergone a major change of direction, driven by the dual needs to develop novel organic electronic materials and to fuel the rapidly emerging nanotechnologies. Among the many diverse fluorescent molecules, the Bodipy family, first developed as luminescent tags and laser dyes, has become a cornerstone for these new applications. The near future looks extremely bright for "porphyrin's little sister".

2,705 citations

Journal ArticleDOI
Jing Zhou1, Qian Liu1, Wei Feng1, Yun Sun1, Fuyou Li1 

1,679 citations

Journal ArticleDOI
TL;DR: The attributes of BODIPY dyes for PDT are summarized, and substituents with appropriate oxidation potentials are summarized in some related areas.
Abstract: BODIPY dyes tend to be highly fluorescent, but their emissions can be attenuated by adding substituents with appropriate oxidation potentials. Substituents like these have electrons to feed into photoexcited BODIPYs, quenching their fluorescence, thereby generating relatively long-lived triplet states. Singlet oxygen is formed when these triplet states interact with 3O2. In tissues, this causes cell damage in regions that are illuminated, and this is the basis of photodynamic therapy (PDT). The PDT agents that are currently approved for clinical use do not feature BODIPYs, but there are many reasons to believe that this situation will change. This review summarizes the attributes of BODIPY dyes for PDT, and in some related areas.

1,599 citations

Journal ArticleDOI
TL;DR: This work focuses on the design and implementation of Activatable Photosensitizer Design Considerations, a very simple and straightforward process that simplifies and automates the very labor-intensive and therefore time-heavy and expensive process of Activation Mechanism Selection.
Abstract: 2. Activatable Photosensitizer Design Considerations 2842 2.1. Activation Strategy 2842 2.2. Photosensitizer Selection 2844 2.3. Photosensitizer Conjugation 2845 3. Examples of Activatable Photosensitizers 2845 3.1. Environment-Activated Photosensitizers 2845 3.2. Enzyme-Activated Photosensitizers 2846 3.3. Nucleic Acid-Activated Photosensitizers 2852 3.4. Other Activation Mechanisms 2853 4. Conclusion and Outlook 2855 5. Abbreviations 2855 6. Acknowledgments 2855 7. References 2855

1,421 citations