Optochemical Control of Therapeutic Agents through Photocatalyzed Isomerization

Winssinger, Nicolas; Watson, Emma E.; Russo, Francesco; Moreau, Dimitri

doi:10.1002/ange.202203390

Cited by 2 publications

(1 citation statement)

References 56 publications

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“…This is understandable as no factors controlling the product selectivity were incorporated into the system. Also, the prolonged light irradiation in the presence of QDs can trigger rapid E-Z isomerization in the stilbene derivatives (see Section 18 of the Supporting Information), − thereby eventually ending up in a mixed ratio of the two isomers (Figure S47). Even though there is a room for improvement with respect to product selectivity, the present study demonstrates the potency of the QD photocatalyst in creating important substituted olefins at high yields in one pot at room temperature using visible light.…”

Section: Resultsmentioning

confidence: 99%

Visible Light-Mediated Quantum Dot Photocatalysis Enables Olefination Reactions at Room Temperature

2023

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The ability of quantum dots (QDs) to photocatalyze organic reactions is gaining attention because of their distinct light harvesting properties over traditional precious metal- and small molecule-based catalysts. However, establishing the potency of QD photocatalysts in diverse and useful organic transformations, as well as deciphering the charge transfer mechanism, is essential to cement their place as an efficient photocatalyst in synthetic chemistry. Here, we report the use of QDs in efficiently catalyzing a series of olefination reactions under visible-light irradiation at room temperature (90% yield). Spectroscopic and electrochemical studies reveal intriguing insights on the charge transfer mechanism involved in QD-photocatalyzed olefination. Interestingly, the dual role of triphenylphosphineas a surface passivating agent and nucleophileturned out to be decisive in directing the charge transfer process from the QD to the reactant. Benzyl triphenylphosphonium bromide salt was accepting the electrons from the photoexcited QDs, thereby initiating the catalytic olefination reaction. QD-photocatalyzed olefination was demonstrated with formaldehyde as well, resulting in the formation of industrially relevant terminal alkene, namely styrene. Moreover, the environmentally friendly indium phosphide (InP) QD also photocatalyzed the olefination reaction under mild reaction conditions, which proves the practical suitability of our study. This work presents an attractive and efficient way to introduce double bonds in organic molecules using QDs and visible light at room temperature.

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Section: Resultsmentioning

confidence: 99%

Visible Light-Mediated Quantum Dot Photocatalysis Enables Olefination Reactions at Room Temperature

2023

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The Development and Application of Opto-Chemical Tools in the Zebrafish

et al. 2022

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The zebrafish is one of the most widely adopted animal models in both basic and translational research. This popularity of the zebrafish results from several advantages such as a high degree of similarity to the human genome, the ease of genetic and chemical perturbations, external fertilization with high fecundity, transparent and fast-developing embryos, and relatively low cost-effective maintenance. In particular, body translucency is a unique feature of zebrafish that is not adequately obtained with other vertebrate organisms. The animal’s distinctive optical clarity and small size therefore make it a successful model for optical modulation and observation. Furthermore, the convenience of microinjection and high embryonic permeability readily allow for efficient delivery of large and small molecules into live animals. Finally, the numerous number of siblings obtained from a single pair of animals offers large replicates and improved statistical analysis of the results. In this review, we describe the development of opto-chemical tools based on various strategies that control biological activities with unprecedented spatiotemporal resolution. We also discuss the reported applications of these tools in zebrafish and highlight the current challenges and future possibilities of opto-chemical approaches, particularly at the single cell level.

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Optochemical Control of Therapeutic Agents through Photocatalyzed Isomerization

Cited by 2 publications

References 56 publications

Visible Light-Mediated Quantum Dot Photocatalysis Enables Olefination Reactions at Room Temperature

Visible Light-Mediated Quantum Dot Photocatalysis Enables Olefination Reactions at Room Temperature

The Development and Application of Opto-Chemical Tools in the Zebrafish

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