Indigo and its derivatives are industrially-important dyes known for centuries. The low solubility of these compounds limits their applications and hinders potential synthetic chemistry using indigo as a building-block. Herein we report attachment of the tert-butoxy carbonyl (tBOC) thermolabile protecting group to indigos, allowing their processing into neat thin films as well as mixed films with a semiconducting polymer. Photoinduced charge transfer is observed to and from these pigments and the polymer.
We report on the synthesis and properties of 6,6′-dithienylindigo (DTI) and poly(DTI). Redox chemistry and ambipolar charge transport with μh = 0.11 cm2 V−1 s−1 and μe = 0.08 cm2 V−1 s−1 and excellent air stability are shown.
Novel unsymmetrical organic sensitizers having donor, π -spacer, and anchoring groups were designed and synthesized for dye-sensitized solar cell (DSSC) application. The dyes 3-{4- [7-(4-{bis[4-(hexyl)phenyl]amino} phenyl)-11,12-dibutoxy-1,4,5,8-tetrahydrodibenzo [a, c] phenazine-2-yl]phenyl} -2-cyano acrylic acid (KD-148) and 3-{5- [7-(4-{bis[4-(hexyloxy)phenyl]amino} phenyl)-11,12-dibutoxy-1,4,5,8-tetrahydrodibenzo [a, c] phenazine-2-yl]-2-thienyl} -2cyano acrylic acid (KD-150) were anchored onto TiO 2 and tested with ionic liquid electrolyte. The monochromatic incident photon-to-current conversion efficiencies (IPCE) of the dyes were 50% and 60% at 420 nm, respectively. The KD-150-sensitized solar cell gave a short-circuit current (I SC ) of 7.37 mA/cm 2 , an open-circuit voltage (V oc) of 560 mV, a fill factor (FF) of 0.56, and overall conversion efficiency ( η) of 2.32% whereas the standard dye Z-907 dye exhibited 14.51 mA/cm 2 of I SC , 630 mV of V oc , 0.45 of FF, and 4.08% of η under AM 1.5 illumination with power of 100 mW/cm 2 .
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