Abstract
Electrochemical and spectroelectrochemical properties of a series of new penta-ring donor–acceptor compounds, comprising 1,3,4-oxadiazole, 1,3,4-thiadiazole, and 1,2,4-triazole central ring, symmetrically connected to substituted bithiophenes, were investigated. Aromaticity and electrophilic–nucleophilic traits of the aza-heterocyclic units, fostering inductive and resonance effects that translate to conjugation enhancement and electron (de)localization, were found a major factor determining the key electron properties of ionization potential (IP) and electron affinity (EA) of these molecules. Replacing the alkyl thiophene substituent for an alkoxy one afforded certain control over the two parameters as well. All studied compounds were found to undergo electrochemical polymerization giving p- and n-dopable products, featuring good electrochemical reversibility of their oxidative doping process, as demonstrated by cyclic voltammetry and UV–vis–NIR, EPR spectroelectrochemistry. While electropolymerization o...
Highlights
In recent years low and high molecular weight organic semiconductors received great attention because of their potential applications in such electronic and electrochemical devices as photovoltaic cells (PCs), photodiodes (PDs), light emitting diodes (LED’s), field effect transistors (FETs), and various types of sensors and electrochromic devices.1–11Appropriate functionalization of these compounds make them solution processable and allows for precise tuning of their electronic, spectroscopic, electrochemical and mechanical properties
It was found that the exclusive contribution to the most intense band in the spectrum is associated with only one transition that is the HOMO→LUMO excitation evidenced by huge value of its oscillator strength
We have demonstrated that penta-ring compounds consisting of an electroaccepting central ring such as 1,3,4-oxadiazole, 1,3,4 - thiadiazole or 1,2,4-triazole, symmetrically connected to substituted bithiophene constitute an interesting class of solution processable electroactive and luminescent semiconductors
Summary
In recent years low and high molecular weight organic semiconductors received great attention because of their potential applications in such electronic and electrochemical devices as photovoltaic cells (PCs), photodiodes (PDs), light emitting diodes (LED’s), field effect transistors (FETs), and various types of sensors and electrochromic devices.. In recent years low and high molecular weight organic semiconductors received great attention because of their potential applications in such electronic and electrochemical devices as photovoltaic cells (PCs), photodiodes (PDs), light emitting diodes (LED’s), field effect transistors (FETs), and various types of sensors and electrochromic devices.1–11 Appropriate functionalization of these compounds make them solution processable and allows for precise tuning of their electronic, spectroscopic, electrochemical and mechanical properties. The experimental findings reported here are theoretically supported by DFT calculations
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