Spectroscopic and electrochemical properties of thiophene-phenylene based Shiff-bases with alkoxy side groups, towards photovoltaic applications

Nitschke, Paweł; Jarząbek, Bożena; Damaceanu, Mariana‐Dana; Bejan, Andra-Elena; Chaber, Paweł

doi:10.1016/j.saa.2020.119242

Cited by 16 publications

(19 citation statements)

References 58 publications

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“…Before assessing the electrochemical behavior of protonated imine molecules in ACN solution, the influence of the molecular structure on the oxidation potentials of the pristine compounds as individual molecules was surveyed. As previously reported for the PAz1 -modified ITO electrode, 19 two oxidation peaks associated with the oxidation of ester-substituted thiophene were recorded for PAz1 in solution, with the onset of the oxidation process ( E onset ox ) at 0.39 V versus Fc/Fc + ( Figure 9 ).…”

Section: Resultssupporting

confidence: 81%

“…Emission spectra of alkoxy-substituted compounds, taken in binary solvents of various dielectric constants, have revealed a positive solvatofluorochromism, suggesting a more effective solvation of the excited molecule and subsequently a better stabilization of the excited states in more polar solvents, similar as that in ref ( 19 ). Apart from that, solvent polarity has affected the protonation process in a similar manner as that during absorption studies.…”

Section: Resultssupporting

confidence: 68%

“…The energy differences between neighboring peaks were found in the range of 0.16–0.22 eV for all studied compounds, with the most intense peaks corresponding to the lowest-energy transitions between 0–0 and 0–1 vibronic levels. 19 The analysis of protonated molecule bands’ positions in terms of energy has highlighted a difference between them of ∼0.2 eV ( Figure 5 ), which clearly indicates that these are vibronic peaks of the absorption band, connected with π → π* electron transitions in the protonated imine.…”

Section: Resultsmentioning

confidence: 96%

“…Results presented herein are compared with the properties of non-protonated counterparts, which were already described in our earlier studies. 9 , 19 …”

Section: Introductionmentioning

confidence: 99%

“…Azomethines (PAzs) are products of condensation (polycondensation) reaction between amines and aldehydes. Such reaction may proceed under mild conditions, using inorganic or organic catalysts or even without using any, as previously shown. , These types of materials were extensively studied due to their interesting thermal, electrical, and optical − properties and also due to the possible activity in some optoelectronic systems, such as bulk heterojunction photovoltaic cells, − perovskite solar cells, − organic light-emitting devices, , or electrochemical systems. , …”

Section: Introductionmentioning

confidence: 99%

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Effect of Protonation on Optical and Electrochemical Properties of Thiophene–Phenylene-Based Schiff Bases with Alkoxy Side Groups

Nitschke

Jarząbek

Bejan³

et al. 2021

J. Phys. Chem. B

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Three polyazomethines and their corresponding model compounds were protonated with trifluoroacetic acid, and its effect on their optical (UV–vis absorption and photoluminescence) properties and electrochemical behavior has been studied, in the context of the presence and elongation of alkoxy side groups. Moreover, the effect of environment dielectric constants (i.e., polarity of the solvent) was considered on the doping process. It has been proven that the presence of alkoxy side groups is necessary for protonation to occur, while unsubstituted compounds undergo hydrolysis to constitutive units. Acid doping of imines consisting of alkoxy side chains has resulted in a distinct bathochromic shift (>200 nm) of the low-energy absorption band. Even the length of alkyl chains has not affected the position of shifted bands; it has been observed that azomethines with smaller, methoxy side groups undergo the protonation process much faster than their octyloxy-substituted analogues, due to the absence of steric hindrance. The electrochemical studies of these alkoxy-substituted imines have indicated a better p-type behavior after protonation induced by the capability of the protonated form to easily oxidize in acetonitrile and to generate the native molecules. The environmental polarity has also had impact on the doping process, which took place only in low-polar media.

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Section: Resultssupporting

confidence: 81%

Section: Resultssupporting

confidence: 68%

Section: Resultsmentioning

confidence: 96%

“…Results presented herein are compared with the properties of non-protonated counterparts, which were already described in our earlier studies. 9 , 19 …”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Effect of Protonation on Optical and Electrochemical Properties of Thiophene–Phenylene-Based Schiff Bases with Alkoxy Side Groups

Nitschke

Jarząbek

Bejan³

et al. 2021

J. Phys. Chem. B

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Hybrid Steroid‐[60]Fullerene as n‐Type Material for Organic Photovoltaics

Lemos,

Perez‐Badell,

Ortiz

et al. 2023

Eur J Org Chem

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Fullerene derivatives have been used as electron acceptor and transport materials in organic photovoltaics as well as in perovskite solar cells. Among them, [6,6]‐phenyl‐C61‐butyric acid methyl ester (PC61BM) has been one of the most widely used, in combination with poly‐3‐hexylthiophene (P3HT) as an electron donor semiconducting polymer, for the fabrication of organic bulk heterojunction solar cells (BHJ‐OSC). In this work, a steroid‐fullerene hybrid was synthesized through the Bingel–Hirsch reaction to compare its properties with PC61BM as the reference structure. Different spectroscopic techniques were employed to characterize the new fullerene derivative, namely 1D and 2D nuclear magnetic resonance (NMR), Fourier Transform Infrared Spectroscopy (FTIR), and high‐resolution mass spectrometry (HRMS). In addition, thermogravimetric analysis (TGA), and cyclic voltammetry were also performed. The characterization was completed by transmission electron microscopy (TEM), which explore the hybrid‘s morphology, where the presence of the steroid moiety increases the solubility of the fullerene material. DFT/PBE−D3(BJ)/6‐311G(d,p) calculations for both the steroid‐fullerene hybrid and PC61BM allowed to obtain geometry optimizations and electronic structure data. A comparative study to analyze the nature of the electronic properties of the synthesized steroid‐[60]fullerene hybrid and PC61BM with an oligomer of ten thiophene units, used in the active layer of organic solar cells, was carried out. Electron density maps using the [CIS|CNDOL/21] approach illustrate the photoexcitation of the donor followed by an electron‐charge transfer to the acceptor fullerene.

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Synthesis, characterization and application of soluble fully conjugated polyazomethine from di‐ or trifunctional monomers

Zang

Takata

et al. 2022

Polymer International

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Fully conjugated polyazomethines (PAZs) exhibit large amounts of micropores among their many short branches in relatively planar structures based on their fully conjugated configuration. However, these fully conjugated structures cause insolubility and non‐processability of the PAZs because they may have strong stacking interactions due to their planar structures. In this paper, to overcome this problem, three short lengths of oligodimethylsiloxane (ODMS) grafts (x = 9, 18 and 39) were introduced by end‐capping reaction of aldehydes at the end of insoluble PAZs with amino‐terminated ODMSs as end‐capping agents. As a result, the insoluble PAZs became almost soluble (solubility > 95–100%) and their molecular weight could be estimated using gel permeation chromatography (Mw = 15.9 × 103 g mol−1). PAZ‐embedded mixed‐matrix membranes (MMMs) were fabricated using blend solutions containing only small amounts (1.0 wt%) of the solubilized PAZs with ODMS grafts and crosslinked polydimethylsiloxane (PDMS). The PAZs/PDMS MMMs showed ultrahigh permeability to oxygen which achieved 8600 barrer without a decrease of the original permselectivity of PDMS. The excellent oxygen permeability of the PAZs/PDMS MMMs may be caused by an effective increase of porosity based on the fully conjugated PAZ nanosheet. © 2022 Society of Industrial Chemistry.

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Spectroscopic and electrochemical properties of thiophene-phenylene based Shiff-bases with alkoxy side groups, towards photovoltaic applications

Cited by 16 publications

References 58 publications

Effect of Protonation on Optical and Electrochemical Properties of Thiophene–Phenylene-Based Schiff Bases with Alkoxy Side Groups

Effect of Protonation on Optical and Electrochemical Properties of Thiophene–Phenylene-Based Schiff Bases with Alkoxy Side Groups

Hybrid Steroid‐[60]Fullerene as n‐Type Material for Organic Photovoltaics

Synthesis, characterization and application of soluble fully conjugated polyazomethine from di‐ or trifunctional monomers

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