Azomethine diimides end-capped with anthracene moieties: Experimental and theoretical investigations

Schab‐Balcerzak, Ewa; Grucela, Marzena; Malecki, Grzegorz; Kotowicz, Sonia; Siwy, Mariola; Janeczek, Henryk; Golba, Sylwia; Praski, Aleksander

doi:10.1016/j.molstruc.2016.09.019

Cited by 6 publications

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“…Asymmetrical 1,8-naphthalimides structures, constructed from a single imide ring, are often tested as compounds substituted in the 4-C position for organic electronics [ 1 , 39 , 40 ]. In the papers [ 8 , 9 , 41 , 42 , 43 , 44 ] the thermal, optical, and electrochemical properties of azomethinediimides, as potential candidates for optoelectronic were presented. To the best of our knowledge, only few papers present naphthalimide derivatives with imine bond substituted in the 4-C or 3-C position investigated towards applications in organic electronics [ 1 , 45 , 46 ].…”

Section: Introductionmentioning

confidence: 99%

New Acceptor–Donor–Acceptor Systems Based on Bis-(Imino-1,8-Naphthalimide)

et al. 2021

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In this paper, six novel symmetrical bis-(imino-1,8-naphthalimides) differing in core and N-substituent structure were synthesized, and their thermal (TGA, DSC), optical (UV-Vis, PL), electrochemical (DPV, CV) properties were evaluated. The compounds were stable to 280 °C and could be transferred into amorphous materials. Electrochemical investigations showed their ability to occur reductions and oxidations processes. They exhibited deep LUMO levels of about −3.22 eV and HOMO levels above −5.80 eV. The optical investigations were carried out in the solutions (polar and non-polar) and in films and blends with PVK:PBD. Bis-(imino-1,8-naphthalimides) absorbed electromagnetic radiation in the range of 243–415 nm and emitted light from blue to yellow. Their capacity for light emission under voltage was preliminarily tested in devices with an active layer consisting of a neat compound and a blend with PVK:PBD. The diodes emitted green or red light.

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Section: Introductionmentioning

confidence: 99%

New Acceptor–Donor–Acceptor Systems Based on Bis-(Imino-1,8-Naphthalimide)

et al. 2021

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“…Although many azomethine derivatives have been prepared and extensively examined, − their concise structure–property relationship remains relatively underexplored. This is particularly the case with conjugated thiophenes that are prepared from 2,5-diamino-3,4-diethylester thiophene, such as 1A and 5 (Figure ).…”

Section: Introductionmentioning

confidence: 99%

Understanding Color Tuning and Reversible Oxidation of Conjugated Azomethines

et al. 2019

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With the aim of achieving reversible oxidation and color tuning, the effect of the central aromatic on the spectroscopic, electrochemical, and spectrochemical properties of a series of electrochromic azomethine triads was investigated. The absorption of the alkylated thiophene derivatives was blue-shifted relative to their unalkylated counterparts when the central aromatic was either a bi-or terthiophene. It was further found that the alkylated thiophene derivatives had larger Stokes shifts than their unsubstituted counterparts. Theoretical calculations demonstrated that the torsion angles of these alkylated cores with respect to the flanking azomethines were responsible for the spectroscopic effects. While the electrochemical oxidation potential of the triads varied by only 100 mV, the reversibility of their anodic process was contingent on the central aromatic. The absorption of the electrochemically produced state red-shifted between 165 and 280 nm from its corresponding neutral state, leading to perceived color changes between orange and blue. Reversible color changes were chemically mediated with ferric chloride/hydrazine. The absorption of the chemically oxidized state shifted between 155 and 220 nm from the corresponding neutral state, contingent on the central aromatic. The palette of perceived colors that was possible with oxidation included orange, yellow, blue, and gray.

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