Is the Greener Approach Better? Application of Electrochemistry in the Synthesis of Perylenediimides
Patrycja Filipek, Agata Szlapa-Kula, Stanisław Krompiec, Krzysztof Zemlak, Bartłomiej Kula, Karol Erfurt, Michał Filapek
TL;DR
This paper explores greener electrochemical methods to synthesize perylenediimides and investigates their optical and electrochemical properties for potential use in optoelectronic devices.
Contribution
The paper introduces a novel electrochemical synthesis of perylenediimides and demonstrates their electrochromic properties and potential for nanographene production.
Findings
Electrochemical synthesis produced perylenediimides with distinct optical emission wavelengths from the same excitation.
Spectroelectrochemical measurements revealed electrochromic properties in the visible and near-infrared range.
A successful pi-expansion of cis-DBPDI via Diels–Alder cycloaddition was achieved, opening opportunities for nanographene synthesis.
Abstract
Perylenediimides are an interesting group of compounds that are finding more and more applications. However, the synthetic route of obtaining and modifying them is usually very complicated, costly, and time-consuming. Therefore, the conducted research aimed to develop new, greener, electrochemical methods of obtaining unknown perylenediimides (containing 2-ethylhexyl at the nitrogen atom). For the products obtained in this way, optical and electrochemical studies were conducted and compared with DFT results (i.e., energy gaps and HOMO and LUMO levels). Asa result of optical studies, different emission wavelengths of two isomers originating from the same excitation wavelength were observed. Electrochemical studies also confirmed significant differences in properties between the obtained isomers. Spectroelectrochemical measurements were also performed; they revealed the electrochromic…
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Taxonomy
TopicsSynthesis and Biological Evaluation · Chemical Synthesis and Reactions · Electrochemical Analysis and Applications