The dark side of photocatalysis: near-infrared photoredox catalysis for organic synthesis

Sellet, Nicolas; Cormier, Morgan; Goddard, Jean‐Philippe

doi:10.1039/d1qo01476e

Cited by 40 publications

(32 citation statements)

References 54 publications

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“…73 The use of near-infrared (NIR) and deep red (DR) light photocatalysis is a promising solution based on its deeper penetration in various media (including tissue). 74 An indirect way to harness red or NIR photons is the use of an sTTA-UC system (see section 3.3.). Here, a low-energy red or NIR photon excites the photosensitizer, which transfers its energy to an annihilator.…”

Section: Red and Near-infrared Photocatalysismentioning

confidence: 99%

Emerging Activation Modes and Techniques in Visible-Light-Photocatalyzed Organic Synthesis

2022

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Visible-light photocatalysis has evolved into a promising mild and sustainable strategy to access radicals. This field unlocks formerly challenging or even previously inaccessible organic transformations. In this review, an overview of some lesser-known modes of photochemical activation of organic molecules and several emerging techniques within the versatile field of visible-light photocatalysis are discussed. These are illustrated by selected photocatalytic reactions, with particular attention given to the reaction mechanism.

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Section: Red and Near-infrared Photocatalysismentioning

confidence: 99%

Emerging Activation Modes and Techniques in Visible-Light-Photocatalyzed Organic Synthesis

2022

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“…On one hand, it can act as an intermediary to transfer its energy to another photocatalyst to initiate a photochemical reaction. On the other hand, the 1 AN* could also serve as a photocatalyst for single electron transfer (SET) to directly catalyze a photoreaction [ 71 , 72 , 73 ]. Two alternative methods provide great convenience, and various types of photochemical reactions have been successfully achieved using porphyrin-based TTA-UC technology.…”

Section: Photochemistry Of Porphyrin-based Tta-uc For Chemical Transf...mentioning

confidence: 99%

Recent Advances in the Photoreactions Triggered by Porphyrin-Based Triplet–Triplet Annihilation Upconversion Systems: Molecular Innovations and Nanoarchitectonics

Yao¹,

Sun²,

He³

et al. 2022

IJMS

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Triplet–triplet annihilation upconversion (TTA-UC) is a very promising technology that could be used to convert low-energy photons to high-energy ones and has been proven to be of great value in various areas. Porphyrins have the characteristics of high molar absorbance, can form a complex with different metal ions and a high proportion of triplet states as well as tunable structures, and thus they are important sensitizers for TTA-UC. Porphyrin-based TTA-UC plays a pivotal role in the TTA-UC systems and has been widely used in many fields such as solar cells, sensing and circularly polarized luminescence. In recent years, applications of porphyrin-based TTA-UC systems for photoinduced reactions have emerged, but have been paid little attention. As a consequence, this review paid close attention to the recent advances in the photoreactions triggered by porphyrin-based TTA-UC systems. First of all, the photochemistry of porphyrin-based TTA-UC for chemical transformations, such as photoisomerization, photocatalytic synthesis, photopolymerization, photodegradation and photochemical/photoelectrochemical water splitting, was discussed in detail, which revealed the different mechanisms of TTA-UC and methods with which to carry out reasonable molecular innovations and nanoarchitectonics to solve the existing problems in practical application. Subsequently, photoreactions driven by porphyrin-based TTA-UC for biomedical applications were demonstrated. Finally, the future developments of porphyrin-based TTA-UC systems for photoreactions were briefly discussed.

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“…In addition, the nearly 50% occupancy of NIR in solar energy provides a clean and infinite source of NIR light [8]. Despite these obvious advantages, NIR light-driven photoredox catalysis was rarely reported [8][9][10], largely due to the poor absorption of NIR light for conventional photocatalysts [3,4]. Currently there are two different approaches to achieve NIR photoredox catalysis.…”

Section: Introductionmentioning

confidence: 99%

Direct Utilization of Near-Infrared Light for Photooxidation with a Metal-Free Photocatalyst

et al. 2022

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Near-infrared (NIR) light-triggered photoredox catalysis is highly desirable because NIR light occupies almost 50% of solar energy and possesses excellent penetrating power in various media. Herein we utilize a metal-free boron dipyrromethene (BODIPY) derivative as the photocatalyst to achieve NIR light (720 nm LED)–driven oxidation of benzylamine derivatives, sulfides, and aryl boronic acids. Compared to blue light–driven photooxidation using Ru(bpy)3Cl2 as a photocatalyst, NIR light–driven photooxidation exhibited solvent independence and superior performance in large-volume (20 mL) reaction, presumably thanks to the neutral structure of a BODIPY photocatalyst and the deeper penetration depth of NIR light. We further demonstrate the application of this metal-free NIR photooxidation to prodrug activation and combination with Cu-catalysis for cross coupling reaction, exhibiting the potential of metal-free NIR photooxidation as a toolbox for organic synthesis and drug development.

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The dark side of photocatalysis: near-infrared photoredox catalysis for organic synthesis

Abstract: Near-Infrared photoredox catalysis is now consider as the next evolution of this field.

Cited by 40 publications

References 54 publications

Emerging Activation Modes and Techniques in Visible-Light-Photocatalyzed Organic Synthesis

Emerging Activation Modes and Techniques in Visible-Light-Photocatalyzed Organic Synthesis

Recent Advances in the Photoreactions Triggered by Porphyrin-Based Triplet–Triplet Annihilation Upconversion Systems: Molecular Innovations and Nanoarchitectonics

Direct Utilization of Near-Infrared Light for Photooxidation with a Metal-Free Photocatalyst

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