TY - JOUR

T1 - Molecular structure – intrinsic photostability relationships for diketopyrrolopyrrole-based conjugated polymers

AU - Kuznetsov, Petr M.

AU - Martynov, Ilya V.

AU - Zhidkov, Ivan s.

AU - Gutsev, Lavrenty G.

AU - Khakina, Ekaterina A.

AU - Zakharchenko, Elena N.

AU - Slesarenko, Nikita A.

AU - Kukharenko, Andrey I.

AU - Troshin, Pavel A.

N1 - This work was supported by the Russian Science Foundation (project no. 22-23-01125). The XPS measurements were supported by the Ministry of Science and Higher Education of the Russian Federation (Ural Federal University Program of Development within the Priority-2030 Program). We acknowledge the contributions of Dr A. V. Akkuratov and Dr I. E. Kuznetsov to the preparation of initial batches of some polymers. NMR measurements were performed using equipment of the Multi-User Analytical Center of the Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry RAS.

PY - 2023

Y1 - 2023

N2 - Widespread practical application of organic solar cells requires their long-term operational stability, a prerequisite which has not yet been achieved. Achieving long device lifetimes depends on the availability of intrinsically stable absorber materials and a thorough understanding of their degradation pathways; both of these aspects are still insufficiently explored. In this work, we present a systematic study of a series of 18 conjugated polymers composed of diketopyrrolopyrrole (DPP) subunits combined with various kinds of other building blocks. It has been shown that the DPP unit itself substantially accelerates the degradation of conjugated polymers due to its favorable photochemical transformation into, as we experimentally and theoretically demonstrate, 1,4-di(thiophen-2-yl)but-2-yne-1,4-diamine (major product) and 1,4-di(thiophen-2-yl)benzene (minor product). Using a set of complementary analytical techniques, we compared the degradation rates of various polymers and established some important correlations between the molecular structures of the materials and their intrinsic photostability. The revealed relationships provide valuable new guidelines for furthering the rational design of new organic absorber materials with largely enhanced photochemical stability. © 2023 The Royal Society of Chemistry.

AB - Widespread practical application of organic solar cells requires their long-term operational stability, a prerequisite which has not yet been achieved. Achieving long device lifetimes depends on the availability of intrinsically stable absorber materials and a thorough understanding of their degradation pathways; both of these aspects are still insufficiently explored. In this work, we present a systematic study of a series of 18 conjugated polymers composed of diketopyrrolopyrrole (DPP) subunits combined with various kinds of other building blocks. It has been shown that the DPP unit itself substantially accelerates the degradation of conjugated polymers due to its favorable photochemical transformation into, as we experimentally and theoretically demonstrate, 1,4-di(thiophen-2-yl)but-2-yne-1,4-diamine (major product) and 1,4-di(thiophen-2-yl)benzene (minor product). Using a set of complementary analytical techniques, we compared the degradation rates of various polymers and established some important correlations between the molecular structures of the materials and their intrinsic photostability. The revealed relationships provide valuable new guidelines for furthering the rational design of new organic absorber materials with largely enhanced photochemical stability. © 2023 The Royal Society of Chemistry.

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U2 - 10.1039/D2TA09402A

DO - 10.1039/D2TA09402A

M3 - Article

VL - 11

SP - 9019

EP - 9028

JO - Journal of Materials Chemistry A

JF - Journal of Materials Chemistry A

SN - 2050-7488

IS - 16

ER -