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Survey of recent advances of in the field of π-conjugated heterocyclic azomethines as materials with tuneable properties

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  • Special Topic Materials Research at Université de Montréal
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Abstract

This account gives an overview of our recent work in the area of conjugated azomethines derived from 2-aminothiophenes. It will be presented that mild reaction conditions can be used to selectively prepare symmetric and unsymmetric conjugated azomethines. It further will be demonstrated that azomethines consisting of various 5-membered aryl heterocycles lead to chemically, reductively, hydrolytically, and oxidatively robust compounds. The optical and electrochemical properties of these materials can be tuned contingent on the degree of conjugation, type of aryl heterocycle, and by including various electronic groups. The end result is materials having colors spanning 250 nm across the visible spectrum. These colors further can be tuned via electrochemical or chemical doping. The resulting doped states have high color contrasts from their corresponding neutral states. The collective opto-electronic properties and the means to readily tune them, make thiophenoazomethine derivatives interesting materials for potential use in a gamut of applications.

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Authors and Affiliations

  1. Laboratoire de Caractérisation Photophysique des Matériaux Conjugués, Département de Chimie, Université de Montréal, CP 6128, Centre-ville, Montreal, QC, H3C 3J7, Canada

    Andréanne Bolduc, Charlotte Mallet & W. G. Skene

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  1. Andréanne Bolduc
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  2. Charlotte Mallet
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  3. W. G. Skene
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Correspondence to W. G. Skene.

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After completing her B.Sc. degree in Chemistry at the Université de Montréal, BOLDUC Andréanne (left) joined Skene’s group as a M. Sc. student in 2008 and then transferred directly into the Ph.D. program. Her thesis focusses on preparing and examining new conjugated azomethines for different plastic electronic applications. MALLET Charlotte (center) completed her Ph.D. studies in 2010 at the Universitéd’Angers, France. She joined Skene’s group as a postdoctoral fellow in 2011, where she works on conjugated benzothiadiazole derivatives for fluorescence applications. SKENE William (right) is an associate professor at U de M. His research interests are the design, synthesis, and characterization of easily prepared conjugated materials for plastic electronics and the structure-property studies of these materials.

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Bolduc, A., Mallet, C. & Skene, W.G. Survey of recent advances of in the field of π-conjugated heterocyclic azomethines as materials with tuneable properties. Sci. China Chem. 56, 3–23 (2013). https://doi.org/10.1007/s11426-012-4778-4

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