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Photoredox reactions that run as radical chains

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Quantum yields of 44, 77, and 18 show product-forming chains—not a closed photocatalytic cycle of Φ ≤ 1—in three visible-light reactions.

Source

Characterizing Chain Processes in Visible Light Photoredox Catalysis

Cismesia MA, Yoon TP · Chemical science · 2015

doi.org/10.1039/c5sc02185eRead the full paper ↗617 citationscc by

What they did

Authors measured 436 nm quantum yields against ferrioxalate (Φ = 1.01; flux 6.67×10−10 E s−1), combined them with luminescence quenching, and compared light/dark experiments on a radical-cation Diels–Alder, a radical-anion [2+2], and an α-alkylation.

What they found

Φ = 44 (Diels–Alder; chain length ~41), Φ = 77 for a [2+2] (chain length Φ/Q = 135), and Φ = 18 for α-alkylation (vs 0.49 in a prior aerobic report). Φ ≫ 1 requires chains; light/dark experiments cannot disprove them.

The limits

What it doesn't show

Not every photoredox reaction is a chain; the authors warn against over-generalizing, and aerobic vs N2 conditions change observed Φ.

Key terms

Quantum yield Φ
Moles of product per einstein of photons; Φ ≫ 1 implies chains.
Chain length
Turnovers per initiation; estimated as Φ or Φ/Q if quenching is incomplete.
Light/dark experiment
Turning the lamp off; cannot prove a closed photoredox loop.
Ferrioxalate actinometry
Φ = 1.01 at 436 nm used to get photon flux.
Ru(bpz)3 2+
Photocatalyst used for the cycloaddition quantum yields.

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Φ ≫ 1 in photoredox means:

Common questions

What Φ means a chain?

Φ much greater than 1.

Diels–Alder Φ?

44, chain length ~41.

Can light/dark rule out chains?

No.

Why was α-alkylation Φ 18 not 0.49?

N2 sparging removes O2 quenching of Ru*.

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