Mechanistic investigation of a visible light mediated dehalogenation/cyclisation reaction using iron(iii), iridium(iii) and ruthenium(ii) photosensitizers

Aydogan, Akin; Bangle, Rachel E.; De Kreijger, Simon; Dickenson, John C.; Singleton, Michael L.; Cauët, Emilie; Cadranel, Alejandro; Meyer, Gerald J.; Elias, Benjamin; Sampaio, Renato N.; Troian-Gautier, Ludovic

doi:10.1039/d1cy01771c

Mechanistic investigation of a visible light mediated dehalogenation/cyclisation reaction using iron(_iii), iridium(_iii) and ruthenium(_ii) photosensitizers

Journal Article · Fri Nov 05 00:00:00 EDT 2021 · Catalysis Science and Technology

DOI:https://doi.org/10.1039/d1cy01771c· OSTI ID:1830362

Aydogan, Akin ^[1]; ^[2]; De Kreijger, Simon ^[1]; ^[2]; ^[1]; ^[3]; ^[4]; ^[2]; ^[1]; ^[5]; ^[1]

Université catholique de Louvain (UCLouvain), Louvain-la-Neuve (Belgium)
Univ. of North Carolina, Chapel Hill, NC (United States)
Université libre de Bruxelles (Belgium)
Friedrich-Alexander-Universitat Erlangen-Nurnberg, Erlangen (Germany); Univ. of Buenos Aires (Argentina)
Univ. of North Carolina, Chapel Hill, NC (United States); Brookhaven National Lab. (BNL), Upton, NY (United States)

The mechanism of a visible light-driven dehalogenation/cyclization reaction was investigated using ruthenium(II), iridium(III) and iron(III) photosensitizers by means of steady-state photoluminescence, time-resolved infrared spectroscopy, and nanosecond/femtosecond transient absorption spectroscopy. The nature of the photosensitizer was found to influence the product distribution such that the dehalogenated, non-cyclized products were only detected for the iron photosensitizer. Strikingly, with the iron photosensitizer, large catalytic yields required a low dielectric solvent such as dichloromethane, consistent with a previous publication. This low dielectric solvent allowed ultrafast charge-separation to outcompete geminate charge recombination and improved cage escape efficiency. Finally, the identification of reaction mechanisms unique to the iron, ruthenium, and iridium photosensitizer represents progress towards the long-sought goal of utilizing earth-abundant, first-row transition metals for emerging energy and environmental applications.

View Accepted Manuscript (DOE)

Research Organization:: Brookhaven National Laboratory (BNL), Upton, NY (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division; National Science Foundation (NSF)

Grant/Contract Number:: SC0012704; SC0021173

OSTI ID:: 1830362

Alternate ID(s):: OSTI ID: 1830265

Report Number(s):: BNL--222409-2021-JAAM

Journal Information:: Catalysis Science and Technology, Journal Name: Catalysis Science and Technology Journal Issue: 24 Vol. 11; ISSN 2044-4753

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

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Mechanistic investigation of a visible light mediated dehalogenation/cyclisation reaction using iron(_iii), iridium(_iii) and ruthenium(_ii) photosensitizers