Design and Synthesis of Thermal Delayed Fluorescence (TADF) Photocatalyst and Its Photocatalytic Dehalogenation Performance

doi:10.6023/cjoc202211015

Abstract

In order to improve the photocatalytic efficiency, a kind of thermal delayed fluorescence (TADF) photocatalyst of tricarbazolyl phthalonitrile was designed and synthesized. A system for the dehalogenation of aryl halohydrocarbons was established, using TADF material as photocatalyst and disulfide as hydrogen transfer catalyst. Different organic halides (including C—Br bonds and C—Cl bonds) can be dehalogenated with moderate to excellent yields. Compared with 2,4,5,6-tetrakis- (carbazol-9-yl)-1,3-dicyanobenzene (4CzIPN), the representative thermal delayed fluorescent material, 4-(N,N-dimethylami- no)-3,5,6-tri(9-carbazolyl)phthalonitrile (3CzDMAPN) has higher catalytic efficiency and specificity.

Key words: photocatalysis, dehalogenation

Cite this article

Yaxin Liu, Yu Zhang, Shuping Luo. Design and Synthesis of Thermal Delayed Fluorescence (TADF) Photocatalyst and Its Photocatalytic Dehalogenation Performance[J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2476-2483.

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Entry	Photocatalyst	Solvent	RSH or RSSR	Additive	Yield/%^b
1	3CzDMAPN	DMSO	(PhS)₂	None	12
2	3CzDMAPN	DMSO	(PhS)₂	AcONa	38
3	3CzDMAPN	DMSO	(PhS)₂	DIPEA	46
4	3CzDMAPN	DMSO	(PhS)₂	HCOOK	74
5	3CzDMAPN	DMSO	(PhS)₂	Cs₂CO₃	n.d.
6	3CzDMAPN	DMSO	(PhS)₂	Na₂CO₃	n.d.
7	3CzDMAPN	DMSO	(PhS)₂	K₃PO₄	0.5
8	3CzDMAPN	DMSO	(PhS)₂	HCOONa	77
9	3CzDMAIPN	DMAc	(PrS)₂	HCOONa	71
10	3CzDMATPN	DMAc	(PrS)₂	HCOONa	74
11	4CzIPN	DMAc	(PrS)₂	HCOONa	53
12	4DPAIPN	DMAc	(PrS)₂	HCOONa	47
13	5CzBN	DMAc	(PrS)₂	HCOONa	n.d.
14	3CzDMAPN	DMF	(PhS)₂	HCOONa	68
15	3CzDMAPN	DMAc	(PhS)₂	HCOONa	83
16	3CzDMAPN	CH₃CN	(PhS)₂	HCOONa	56
17	3CzDMAPN	NMP	(PhS)₂	HCOONa	76
18	3CzDMAPN	EtOAc	(PhS)₂	HCOONa	49
19	3CzDMAPN	DMAc	(ⁿPrS)₂	HCOONa	93
20	3CzDMAPN	DMAc	(ⁱPrS)₂	HCOONa	84
21	3CzDMAPN	DMAc	(CyS)₂	HCOONa	62
22	3CzDMAPN	DMAc	(^tBuS)₂	HCOONa	65
23	3CzDMAPN	DMAc	Triisopropylsilanethiol	HCOONa	59
24	3CzDMAPN	DMAc	2,4,6-Triisopropylbenzenethiol	HCOONa	52

Entry	Photocatalyst	Solvent	RSH or RSSR	Additive	Yield/%^b
1	3CzDMAPN	DMSO	(PhS)₂	None	12
2	3CzDMAPN	DMSO	(PhS)₂	AcONa	38
3	3CzDMAPN	DMSO	(PhS)₂	DIPEA	46
4	3CzDMAPN	DMSO	(PhS)₂	HCOOK	74
5	3CzDMAPN	DMSO	(PhS)₂	Cs₂CO₃	n.d.
6	3CzDMAPN	DMSO	(PhS)₂	Na₂CO₃	n.d.
7	3CzDMAPN	DMSO	(PhS)₂	K₃PO₄	0.5
8	3CzDMAPN	DMSO	(PhS)₂	HCOONa	77
9	3CzDMAIPN	DMAc	(PrS)₂	HCOONa	71
10	3CzDMATPN	DMAc	(PrS)₂	HCOONa	74
11	4CzIPN	DMAc	(PrS)₂	HCOONa	53
12	4DPAIPN	DMAc	(PrS)₂	HCOONa	47
13	5CzBN	DMAc	(PrS)₂	HCOONa	n.d.
14	3CzDMAPN	DMF	(PhS)₂	HCOONa	68
15	3CzDMAPN	DMAc	(PhS)₂	HCOONa	83
16	3CzDMAPN	CH₃CN	(PhS)₂	HCOONa	56
17	3CzDMAPN	NMP	(PhS)₂	HCOONa	76
18	3CzDMAPN	EtOAc	(PhS)₂	HCOONa	49
19	3CzDMAPN	DMAc	(ⁿPrS)₂	HCOONa	93
20	3CzDMAPN	DMAc	(ⁱPrS)₂	HCOONa	84
21	3CzDMAPN	DMAc	(CyS)₂	HCOONa	62
22	3CzDMAPN	DMAc	(^tBuS)₂	HCOONa	65
23	3CzDMAPN	DMAc	Triisopropylsilanethiol	HCOONa	59
24	3CzDMAPN	DMAc	2,4,6-Triisopropylbenzenethiol	HCOONa	52

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