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Indeno[1,2-b]thiophene End-capped Perylene Diimide: Should the 1,6-Regioisomers be systematically considered as a byproduct?

ABSTRACT: Usually considered as a byproduct, the 1,6-dibrominated PDI has rarely been functionalized for the preparation of electro-active conjugated molecules, particularly in the field of organic photovoltaics. In light of the literature, one can ask oneself: Does a 1,7-isomer based functional molecule systematically perform better than its 1,6-analogue? To answer this question, we report herein the synthesis and direct comparison of two indeno[1,2-b]thiophene (IDT) end-capped perylene diimide regioisomers (PDI) (1,6 and 1,7) used as non-fullerene acceptors in organic solar cells. It turned out that in our case, ie, when blended with the well-known PTB7-Th donor polymer, higher performance was reached for devices made with the 1,6-analogue.

SUBMITTER: Simon Marques P

PROVIDER: S-EPMC7039957 | biostudies-literature | 2020 Feb

REPOSITORIES: biostudies-literature

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Indeno[1,2-b]thiophene End-capped Perylene Diimide: Should the 1,6-Regioisomers be systematically considered as a byproduct?

Simón Marqués Pablo P Tintori Francesco F Andrés Castán José María JM Josse Pierre P Dalinot Clément C Allain Magali M Welch Gregory G Blanchard Philippe P Cabanetos Clément C

Scientific reports 20200224 1

Usually considered as a byproduct, the 1,6-dibrominated PDI has rarely been functionalized for the preparation of electro-active conjugated molecules, particularly in the field of organic photovoltaics. In light of the literature, one can ask oneself: Does a 1,7-isomer based functional molecule systematically perform better than its 1,6-analogue? To answer this question, we report herein the synthesis and direct comparison of two indeno[1,2-b]thiophene (IDT) end-capped perylene diimide regioisom ...[more]

PMID: 32094356

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Project description:The uricosuric diuretic agent tienilic acid (TA) is a thiophene-containing compound that is metabolized by P450 2C9 to 5-OH-TA. A reactive metabolite of TA also forms a covalent adduct to P450 2C9 that inactivates the enzyme and initiates immune-mediated hepatic injury in humans, purportedly through a thiophene-S-oxide intermediate. The 3-thenoyl regioisomer of TA, tienilic acid isomer (TAI), is chemically very similar and is reported to be oxidized by P450 2C9 to a thiophene-S-oxide, yet it is not a mechanism-based inactivator (MBI) of P450 2C9 and is reported to be an intrinsic hepatotoxin in rats. The goal of the work presented in this article was to identify the reactive metabolites of TA and TAI by the characterization of products derived from P450 2C9-mediated oxidation. In addition, in silico approaches were used to better understand both the mechanisms of oxidation of TA and TAI and/or the structural rearrangements of oxidized thiophene compounds. Incubation of TA with P450 2C9 and NADPH yielded the well-characterized 5-OH-TA metabolite as the major product. However, contrary to previous reports, it was found that TAI was oxidized to two different types of reactive intermediates that ultimately lead to two types of products, a pair of hydroxythiophene/thiolactone tautomers and an S-oxide dimer. Both TA and TAI incorporated ¹?O from ¹?O? into their respective hydroxythiophene/thiolactone metabolites indicating that these products are derived from an arene oxide pathway. Intrinsic reaction coordinate calculations of the rearrangement reactions of the model compound 2-acetylthiophene-S-oxide showed that a 1,5-oxygen migration mechanism is energetically unfavorable and does not yield the 5-OH product but instead yields a six-membered oxathiine ring. Therefore, arene oxide formation and subsequent NIH-shift rearrangement remains the favored mechanism for formation of 5-OH-TA. This also implicates the arene oxide as the initiating factor in TA induced liver injury via covalent modification of P450 2C9. Finally, in silico modeling of P450 2C9 active site ligand interactions with TA using the catalytically active iron-oxo species revealed significant differences in the orientations of TA and TAI in the active site, which correlated well with experimental results showing that TA was oxidized only to a ring carbon hydroxylated product, whereas TAI formed both ring carbon hydroxylated products and an S-oxide.

Dataset Information

Indeno[1,2-b]thiophene End-capped Perylene Diimide: Should the 1,6-Regioisomers be systematically considered as a byproduct?

Publications

Indeno[1,2-b]thiophene End-capped Perylene Diimide: Should the 1,6-Regioisomers be systematically considered as a byproduct?

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