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Synthesis and Characterization of New Conjugated Azomethines End-Capped with Amino-thiophene-3,4-dicarboxylic Acid Diethyl Ester.

ABSTRACT: A new series of thiophene-based azomethines differing in the core structure was synthesized. The effect of the central core structure in azomethines on the thermal, optical and electrochemical properties was investigated. The obtained compounds exhibited the ability to form a stable amorphous phase with a high glass transition temperature above 100 °C. They were electrochemically active and undergo oxidation and reduction processes. The highest occupied (HOMO) and the lowest unoccupied molecular (LUMO) orbitals were in the range of -3.86--3.60 eV and -5.46--5.17 eV, respectively, resulting in a very low energy band gap below 1.7 eV. Optical investigations were performed in the solvents with various polarity and in the solid state as a thin film deposited on a glass substrate. The synthesized imines absorbed radiation from 350 to 600 nm, depending on its structure and showed weak emission with a photoluminescence quantum yield below 2.5%. The photophysical investigations were supported by theoretical calculations using the density functional theory. The synthesized imines doped with lithium bis-(trifluoromethanesulfonyl)imide were examined as hole transporting materials (HTM) in hybrid inorganic-organic perovskite solar cells. It was found that both a volume of lithium salt and core imine structure significantly impact device performance. The best power conversion efficiency (PCE), being about 35-63% higher compared to other devices, exhibited cells based on the imine containing a core tiphenylamine unit.

SUBMITTER: Pajak AK

PROVIDER: S-EPMC9330727 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Project description:The development of the modern society imposes a fast-growing demand for new advanced functional polymer materials. To this aim, one of the most plausible current methodologies is the end-group functionalization of existing conventional polymers. If the end functional group is able to polymerize, this method enables the synthesis of a molecularly complex, grafted architecture that opens the access to a wider range of material properties, as well as tailoring the special functions required for certain applications. In this context, the present paper reports on α-thienyl-ω-hydroxyl-end-groups functionalized oligo-(D,L-lactide) (Th-PDLLA), which was designed to combine the polymerizability and photophysical properties of thiophene with the biocompatibility and biodegradability of poly-(D,L-lactide). Th-PDLLA was synthesized using the path of "functional initiator" in the ring-opening polymerization (ROP) of (D,L)-lactide, assisted by stannous 2-ethyl hexanoate (Sn(oct)2). The results of NMR and FT-IR spectroscopic methods confirmed the Th-PDLLA's expected structure, while the oligomeric nature of Th-PDLLA, as resulting from the calculations based on 1H-NMR data, is supported by the findings from gel permeation chromatography (GPC) and by the results of the thermal analyses. The behavior of Th-PDLLA in different organic solvents, evaluated by UV-vis and fluorescence spectroscopy, but also by dynamic light scattering (DLS), suggested the presence of colloidal supramolecular structures, underlining the nature of the macromonomer Th-PDLLA as an "shape amphiphile". To test its functionality, the ability of Th-PDLLA to work as a building block for the synthesis of molecular composites was demonstrated by photoinduced oxidative homopolymerization in the presence of diphenyliodonium salt (DPI). The occurrence of a polymerization process, with the formation of a thiophene-conjugated oligomeric main chain grafted with oligomeric PDLLA, was proven, in addition to the visual changes, by the results of GPC, 1H-NMR, FT-IR, UV-vis and fluorescence measurements.

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Synthesis and Characterization of New Conjugated Azomethines End-Capped with Amino-thiophene-3,4-dicarboxylic Acid Diethyl Ester.

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