Naphthalene diimides (NDIs) have great potential for application to electrochromic Smart Windows due to their colourless native states, highly stable dark reduced states (due to a highly coloured radical anion or dianion produced both photo-and electrochemically) and fast switching times. NDIs functionalised with simple amino acids and dipeptides have advantages of facile synthesis, low cost and operating conditions (low redox potentials), and solubility in water. The effectiveness of each NDI is affected by the aggregated state used, which is affected by both functional group and the absolute pH used. We report a number of systems which demonstrate darkest colouration upon reduction and fastest electrochemical oxidation at an ‘ideal’ pH. We deduce that aggregation has a significant effect upon chromic properties of these systems and evaluate their long-term use within a Smart Window electrochromic device in their individual ideal aggregated states.

Effect of pH and functionalisation of self-assembled Naphthalene-diimides for smart window applications

ACS Fall 2021

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