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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2209323Generated: October 25, 2026

Potassium Phosphate, Tribasic → Diketopyrrolopyrrole

https://huagongshe.com/reaction/2209323

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPotassium Phosphate, TribasicHCID 62657—
ReactantToluene waterHCID 22272177—
Reactant3,7-dibromo-1,5-dihexyl-1H,5H-pyrrolo[2,3-f]indole-2,6-dioneHCID 86698271—
Reactant2,5-Bis(2-octyldodecyl)-3,6-bis(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dioneHCID 86698272—
CatalystTri-tert-butylphosphine tetrafluoroborateHCID 2734635—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
SolventMethanolHCID 887—
ProductDiketopyrrolopyrroleHCID 23363597655.1%

Reaction Steps

A mixture of 3,7-dibromo-1,5-dihexyl-1H,5H-pyrrolo[2,3-f]indole-2,6-dione (0.075 g, 0.148 mmol), 2,5-dihydro-2,5-bis(2-octyldodecyl)-3,6-bis[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-thienyl]-pyrrolo[3,4-c]pyrrole-1,4-dione (0.168 g, 0.150 mmol), Pd2(dba)3 (4.0 mg), tri-tert-butylphosphonium tetrafluoroborate (2.0 mg), K3PO4 (0.095 g) and toluene/H2O (8 mL/0.5 mL) was heated at reflux for 48 h. Then after cooling to room temperature, the mixture was dropped into methanol to precipitate. After being filtered and dried, the precipitation was Soxhlet extracted with methanol, acetone, hexane, dichloromethane and chloroform in succession. The chloroform solution was concentrated and reprecipitated in methanol. The solid was filtered and dried to yield polymer (0.130 g, 72.6%) as a black solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09379335B2
Source datasetuspto-grants-2016_06
ORD IDord-d2b0ddf35b62419fbba365b5389431d6
Source noteuspto-grants-2016_06