Visible-to-NIR Electrochromic Device Prepared from a Thermally Polymerizable Electroactive Organic Monomer

A monomer (1) consisting of a benzothiadiazole core flanked by two triphenylamines and two styrene pendant moieties was prepared. The monomer was fluorescent with its emission spanning 145 nm in the visible, contingent on the organic solvent used for the measurement. In addition to its positive solvatochromism, the absolute fluorescence quantum yield (Φ_fl) was consistently >20% with values >80% being measured in hexane, toluene, diethyl ether, and toluene. 1 could be reversibly oxidized with an oxidation potential of 880 mV vs SCE. The monomer could be immobilized on ITO-coated glass substrates. The resulting 425 nm thick immobilized film (poly-1) was 15% thinner than the monomer coating deposited by spray- and spin-coating. The electroactive film did not delaminate from the electrode upon either washing or cycling electrochemically between its oxidized and neutral states. Its absorption at 460 nm bleached upon electrochemical oxidation with the formation of a strong absorption at 880 nm and in the NIR, similar to 1. The perceived reversible color change with applied potential switched between yellow and gray. The fluorescence intensity of poly-1 could be switched with applied potentials. A passive transmissive device prepared from poly-1 was both electrochromic and fluorochromic, exhibiting reversible color change and fluorescence quenching.