A new series of electron-deficient molecules based on a central benzothiadiazole moiety flanked with vinylimides has been synthesized via Heck chemistry and used in solution-processed organic photovoltaics (OPV). Two new compounds, 4,7-bis(4-(N-hexyl-phthalimide)vinyl)benzo[c]1,2,5-thiadiazole (PI-BT) and 4,7-bis(4-(N-hexyl-naphthalimide)vinyl)benzo[c]1,2,5-thiadiazole (NI-BT), show significantly different behaviors in bulk heterojunction (BHJ) solar cells using poly(3-hexylthiophene) (P3HT) as the electron donor. Two-dimensional grazing incidence X-ray scattering (2D GIXS) experiments demonstrate that PI-BT shows significant crystallization in spin-coated thin films, whereas NI-BT does not. Density functional theory (DFT) calculations predict that while PI-BT maintains a planar structure in the ground state, steric interactions cause a twist in the NI-BT molecule, likely preventing significant crystallization. In BHJ solar cells with P3HT as donor, PI-BT devices achieved a large open-circuit voltage of 0.96 V and a maximum device power-conversion efficiency of 2.54%, whereas NI-BT containing devices only achieved 0.1% power-conversion efficiency. © 2011 American Chemical Society.
|Original language||English (US)|
|Number of pages||7|
|Journal||Chemistry of Materials|
|State||Published - Dec 27 2011|