Optimization of the reaction condition.

Entrya	Sensitizer	Annihilator	Solvent	NMR yield
1b	[Ru]2+	Pyrene	SDS (4 wt%)	62
2b	[Ru]2+	Pyrene	Triton-X-100 (4 wt%)	48
3b	[Ru]2+	Pyrene	CTAC (4 wt%)	12
4c	[Ru]2+	Pyrene	SDS (4 wt%)	76 (80d)
5c	[Ru]2+	Pyrene	Acetonitrile, no O2	52
6c	[Ru]2+	Pyrene	DCM, no O2	45
7c	[Ru]2+	Pyrene	MeOH, no O2	84 (79d)
8c	[Ru]2+	Pyrene	MeOH	64
9c	[Ru]2+	Pyrene	SDS (4 wt%), no O2	79
10c	[Ru]2+	Pyrene	H2O, no O2	22
11c	[Ru]2+	—	SDS (4 wt%)	28
12c	—	Pyrene	SDS (4 wt%)	0
13c	—	—	SDS (4 wt%)	0
14e	[Ru]2+	Pyrene	SDS (4 wt%)	0

^aFor the determination of the NMR yield, toluene (5.3 μL, 0.05 mmol) was used as internal standard.

^b3 W 520 nm LED.

^c10 W 520 nm LED.

^dYields of isolated product.

^eNo light. SDS = sodium dodecyl sulfate, CTAC = cetyltrimethylammonium chloride.