Issue 23, 2023

Exploring SiliaCat Pd-DPP as a recyclable heterogeneous catalyst for the multi-batch direct heteroarylation polymerization for P(NDI2OD-T2)

Abstract

Donor–acceptor (D–A) conjugated polymers like P(NDI2OD-T2) are important constituents of the active layer of energy conversion devices like all-polymer solar cells. A cost-effective and environmentally amiable pathway for the synthesis of this and similar D–A polymers is highly desirable for the large-scale production of these materials. In this report we have combined two cost-effective approaches, namely, direct heteroarylation polymerization (DHAP) and a recyclable heterogeneous catalyst (SiliaCat Pd-DPP), for the multi-batch synthesis of P(NDI2OD-T2). The general applicability of the approach was first established with a series of conjugated small molecules based on naphthalene diimide and bithiophene derivatives (N1 to N6). The Meitlis hot filtration test and inductively coupled plasma-optical emission spectroscopy (ICP-OES) were conducted to estimate the quantity of leached palladium in the final reaction product. Catalyst recyclability up to five cycles was demonstrated for N1 with <2 ppm leached palladium impurity. A comparison was made with the homogeneous catalyst Pd2dba3 which indicated the presence of much higher levels of palladium impurity in the final product. The polymerization of P(NDI2OD-T2) was demonstrated using the regular monomers (NDIOD-Br2 and bithiophene) and also using a modified monomer with activated bithiophene (naphthalene diimide substituted bithiophene) under DHAP conditions employing SiliaCat Pd-DPP as the recyclable heterogeneous catalyst. The modified monomer proved to be amenable to DHAP polymerization using SiliaCat Pd-DPP as the heterogeneous catalyst, which could be consecutively reused four times with reproducible molecular weights in the range of Mn/Mw: 27.1/49.0 to 33.5/61.3.

Graphical abstract: Exploring SiliaCat Pd-DPP as a recyclable heterogeneous catalyst for the multi-batch direct heteroarylation polymerization for P(NDI2OD-T2)

Supplementary files

Article information

Article type
Paper
Submitted
18 Feb 2023
Accepted
12 Mei 2023
First published
16 Mei 2023

Polym. Chem., 2023,14, 2803-2819

Exploring SiliaCat Pd-DPP as a recyclable heterogeneous catalyst for the multi-batch direct heteroarylation polymerization for P(NDI2OD-T2)

N. R. Kakde and A. S. K., Polym. Chem., 2023, 14, 2803 DOI: 10.1039/D3PY00183K

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