Preparation of Semiconducting Films By Electrooxidation of Naphthalene

Abstract

Due to promising electronic and optical properties, conductive polymers are attracting significant interest. Conductive polymers find applications in electronic devices, e.g. substituted polynaphthalenes are used as blue light sources in OLEDs1. The ability to block the substitution sites where the subsequent polymer unit may be added by functional groups allows the polymer structure to be designed2. Moreover, one of the benefits of conductive polymers is the ability to modify the band gap of these materials by adding substituents to the main chain.Naphthalene, as the smallest polycyclic hydrocarbon, is an interesting precursor for synthesis semiconducting materials. The anodic oxidation of naphthalene has been described several times in the literature3,4, however, only formation of 1,4-polynaphthalene in the form of a granular product has been reported.In our research, we performed naphthalene electrooxidation and investigated the impact of the experimental conditions such as naphthalene concentration, water content, and electrode material on the obtained semiconducting materials. We used mass spectrometry to observe mass progression and determine molecular mass of the obtained polymers. The results of electron microscopy imaging showed fine quality coating. We studied the electronic properties of the polymers by cyclic voltammetry and impedance spectroscopy. Based on the results, we discussed the possible mechanism of the reaction. Samanta, S. K. et al. Synthesis of high molecular weight 1,4-polynaphthalene for solution-processed true color blue light emitting diode. Macromolecules 51, 8324–8329 (2018).Debad, J. F. & Bard, A. J. Electropolymerization of acenaphtho[1,2-k]fluoranthene derivatives: Formation of a new conductive electroactive electrochromic hydrocarbon ladder polymer. J Am Chem Soc 120, 2476–2477 (1998).Zecchin, S., Tomat, R., Schiavon, G. & Zotti, G. Polynaphthylene films from anodic coupling of naphthalene. Synthetic Metals vol. 25 (1988).Huang, Z., Qu, L., Shi, G., Chen, F. & Hong, X. Electrochemical polymerization of naphthalene in the electrolyte of boron trifluoride diethyl etherate containing trifluoroacetic acid and polyethylene glycol oligomer. Journal of Electroanalytical Chemistry 556, 159–165 (2003).