Synthesis and electropolymerization of a multifunctional naphthalimide clicked carbazole derivative

Abstract

In this study, a multifunctional 'clicked' naphthalimide carbazole derivative (CNaP) was synthesized via Huisgen 1,3-dipolar cycloaddition reaction. Combining carbazole as an electroactive group with naphthalimide as a fluorescence group via click chemistry imparts multifunctional properties to this unique structure. CNaP was characterized via Fourier transform IR, C-13 and H-1 NMR spectroscopy as well as fluorescence and electrochemical measurements. The electrochemical polymerization of the CNaP monomer was carried out in acetonitrile/boron trifluoride diethyl etherate (2:1) (v/v) by the cyclic voltammetry technique. The resulting polycarbazole-derived conductive polymer was characterized via optical and electrochemical measurements. PCNaP displayed multi-electrochromism behaviour with good optical contrast (41% at 693 nm) and switching time (1.92 s at 693 nm). These results demonstrate that the new 'clicked' fluorescent, polycarbazole-derived conductive polymer can be used in various applications such as electrochemical/optical sensors and electrochromic and fluorescence imaging devices. (c) 2019 Society of Chemical Industry