Research Highlights

Cross-Linkable Fluorene-Diphenylamine Derivatives For

Silja Abraham, Gayathri Prabhu T. Ganesh, Sunil Varughese, Biswapriya Deb, and Joshy Joseph*

Cross-Linkable Fluorene-Diphenylamine Derivatives for Electrochromic Applications

Multicolor electrochromic systems based on heat cross-linkable arylamine-substituted fluorene derivatives, FD and FDOMe, are reported. These derivatives with pendant vinyl groups have been synthesized by the Buchwald–Hartwig amination reaction and were well-characterized using various analytical and spectroscopic techniques such as NMR, ESI-MS, and single-crystal X-ray diffraction analysis. FD and FDOMe exhibited thermally activated cross-linking above their melting temperatures, which was confirmed through absorption, differential scanning calorimetry (DSC), FT-IR, and wide-angle X-ray diffraction (WAXD) techniques. Cross-linked FD films (FD-X) on ITO showed two reversible redox peaks at 0.74 and 0.91 V (versus Ag/AgCl) that correspond to the formation of radical cations and dications, respectively. The corresponding redox peaks were observed at 0.6 and 0.8 V for cross-linked FDOMe films (FDOMe-X). Spectroelectrochemical studies of the electrochromic films on ITO revealed multicolor electrochromism of FD-X (colorless–yellow–dark cyan) and FDOMe-X (colorless–brick red–blue) with a color contrast of ∼44% at 485 nm for FD-X and ∼63% at 500 nm for FDOMe-X and good switching stability between the neutral and oxidized states (>300 cycles) with low switching voltages(less than 0.9 V for the first oxidation and less than 1.3 V for the second oxidation). Furthermore, fabrication of electrochromic devices using FD-X and FDOMe-X on FTO substrate with PMMA-based solid electrolyte was demonstrated, where the devices exhibited reasonably low switching time between the redox states (less than 30 s) with good optical contrast.

ACS Appl. Mater. Interfaces, 2015,7 (45), pp 25424–25433

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