A new conducting polymer bearing 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) subunit: Synthesis and characterization

A new monomer system based on thiophene, pyrrole and 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene dye (SNS-BODIPY) was synthesized and its corresponding polymer (PSNS-BODIPY) was obtained via repetitive cycling or constant potential electrolysis in 0.1 M tetrabutylammonium hexafluorophosphate dissolved in dichloromethane. The PSNS-BODIPY film has very stable and well-defined reversible redox couples during p-doping process. Multi-electrochromic polymer film has a band gap of 2.9 eV with two absorption bands in its neutral state at 351 and 525 nm, attributed to the polymer backbone and BODIPY subunits, respectively. The percentage transmittance changes between both states (neutral and oxidized) were found as 12.1% for 351 nm and 17.7% for 525 nm in the visible region as well as 46.2% for 1050 nm in the near-infrared region. Beyond the robustness, the PSNS-BODIPY film has high redox stability (retaining 53.3% of its electroactivity at 351 nm after 2000 switching) with a low response time of 1.0 s. (C) 2008 Elsevier Ltd. All rights reserved.