Journal
CHEMISTRY OF MATERIALS
Volume 23, Issue 24, Pages 5484-5490Publisher
AMER CHEMICAL SOC
DOI: 10.1021/cm203111k
Keywords
organic electronics; solar cells; photovoltaic devices; electron acceptors; n-type materials
Funding
- Center for Advanced Molecular Photovoltaics (CAMP), King Abdullah University of Science and Technology (KAUST) [KUS-C1-015-21]
- Global Climate and Energy Project (GCEP) [1138721]
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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-hexylnaphthalimide)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 02 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 (.) E 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.
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