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2. Coumarins: their versatile use in photoredox catalysis and biological applications.

Author

Cozzi, Pier Giorgio, Jansen, Thomas Paul, Rodeghiero, Giacomo <1986>, Cozzi, Pier Giorgio, Jansen, Thomas Paul, and Rodeghiero, Giacomo <1986>

Abstract

Coumarin dyes have proven to posses unique photophysical properties thanks to the high quantum yield, and stability and an absorption and emission which cover the most part of the visible spectrum. In particular, a peculiar characteristic of this class of fluorophores is the large Stokes shift. Thanks to these exceptional photophysical properties, coumarin dyes are widespread used in different applications including fluorescent bio-label, emitting materials in OLED and dyes in solar cells as example. To the best of our knowledge their systematic use in photoredox catalysis has not been explore yet. This research aimed at the design, the synthesis, the photophysical characterization of new LSS coumarin dyes and their use in different fields such as photoredox catalysis, photopolymerization and biological applications (bioconiugation and fluorescent microscopy).

Published
2020

5. Allylation of aldehydes by dual photoredox and nickel catalysis

Author

Gualandi, Andrea, primary, Rodeghiero, Giacomo, additional, Faraone, Adriana, additional, Patuzzo, Filippo, additional, Marchini, Marianna, additional, Calogero, Francesco, additional, Perciaccante, Rossana, additional, Jansen, Thomas Paul, additional, Ceroni, Paola, additional, and Cozzi, Pier Giorgio, additional

Published
2019
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6. Catalytic Photoredox Allylation of Aldehydes Promoted by a Cobalt Complex.

Author

Gualandi, Andrea, Rodeghiero, Giacomo, Perciaccante, Rossana, Jansen, Thomas Paul, Moreno‐Cabrerizo, Cristina, Foucher, Charles, Marchini, Marianna, Ceroni, Paola, and Cozzi, Pier Giorgio

Subjects
ALLYLATION, COBALT, ALLYL compounds, ALDEHYDES, ORGANIC chemistry
Abstract

The preparation of homoallylic alcohols by addition of organometallic allyl compounds to carbonyls is an important strategy in organic chemistry. Allylating organometallic cobalt species can be generated employing stoichiometric quantities of Zn acting as reductant. To avoid the employment of stoichiometric amount of Zn, we have developed an allylation reaction of aromatic and aliphatic aldehydes promoted by photoredox catalysis in the presence of a cobalt complex, and we present herein a full account of our research. In the presence of the abundant CoBr2 (10 mol %), 4,4′‐di‐tert‐butyl‐2,2′‐dipyridyl (dtbbpy, 10 mol %), allyl acetate (3 equiv.), [Ir(dtbbpy)(ppy)2]PF6 (ppy=2‐phenylpyridine, 2 mol %), and N,N‐diisopropylethylamine (4 equiv.), an allylation of aldehydes is taking place, in moderate to good yields. Substrates scope, limitations, and photophysical investigations of this new process are reported. [ABSTRACT FROM AUTHOR]

Published
2021
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7. Application of coumarin dyes for organic photoredox catalysis

Author

Gualandi, Andrea, primary, Rodeghiero, Giacomo, additional, Della Rocca, Emanuele, additional, Bertoni, Francesco, additional, Marchini, Marianna, additional, Perciaccante, Rossana, additional, Jansen, Thomas Paul, additional, Ceroni, Paola, additional, and Cozzi, Pier Giorgio, additional

Published
2018
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8. Application of coumarin dyes for organic photoredox catalysis

Author

Francesco Bertoni, Giacomo Rodeghiero, Thomas Paul Jansen, Paola Ceroni, Marianna Marchini, Emanuele Della Rocca, Pier Giorgio Cozzi, Rossana Perciaccante, Andrea Gualandi, Gualandi, Andrea, Rodeghiero, Giacomo, Della Rocca, Emanuele, Bertoni, Francesco, Marchini, Marianna, Perciaccante, Rossana, Jansen, Thomas Paul, Ceroni, Paola, and Cozzi, Pier Giorgio

Subjects
Steric effects, TRANSFORMATIONS, Reducing agent, Radical polymerization, 010402 general chemistry, 01 natural sciences, Catalysis, CARBONYL DERIVATIVES, chemistry.chemical_compound, Materials Chemistry, Triplet state, ALDEHYDES, 010405 organic chemistry, Pinacol, Metals and Alloys, Photoredox catalysis, General Chemistry, DRIVEN, Coumarin, Combinatorial chemistry, TRIPLET-STATE, 0104 chemical sciences, Surfaces, Coatings and Films, Electronic, Optical and Magnetic Materials, BONDS, chemistry, Ceramics and Composites, FUNCTIONALIZATION, Surface modification, RADICAL POLYMERIZATION, METAL-COMPLEXES, VISIBLE-LIGHT
Abstract

Here we report the application of readily prepared and available coumarin dyes for photoredox catalysis, which are able to mimic powerful reductant [Ir(iii)] complexes. Coumarin derivatives 9 and 10 were employed as photoreductants in pinacol coupling and in other reactions, in the presence of Et3N as a sacrificial reducing agent. As the electronic, photophysical, and steric properties of coumarins could be varied, a wide applicability to several classes of photoredox reactions is predicted.

Published
2018

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