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Abstract Four cross‐conjugated molecules based on the benzo[1,2‐d:4,5‐d’]bisoxazole (BBO) moiety have been synthesized from a common synthon. Theoretical studies indicated that these cruciforms had highly segregated HOMO and LUMO levels enabling semi‐autonomous tuning of the LUMO level from the HOMO through substitution along the 2,6‐axis. The experimental data confirms that the HOMO levels within these systems varied by 0.3 eV, whereas the LUMO levels varied by over 1.6 eV when the electron‐density along the 2,6‐axis was increased. The introduction of relatively electron‐deficient moieties along the 2,6‐axis resulted in a bathochromic shift in the absorption profiles concurrent with the stabilization of the LUMO. These substituents also prolonged the photoluminescent lifetimes owing to improved intramolecular charge transfer states between the 4,8‐ and 2,6‐ axis. The BBO cruciforms were evaluated as donor materials in organic solar cells (OSC)s, but the energy‐level mismatches and poor thin film morphology led to poor performance. These results indicate that benzobisoxazole cruciforms are a promising platform for the development of tunable materials for use in organic semiconductors, but improvements in the optical, electronic and film‐forming properties are needed to enable their use in efficient OSCs.
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A p-π* conjugated triarylborane as an alcohol-processable n-type semiconductor for organic optoelectronic devices
We report a p-π* conjugated organic molecule based on triarylborane as n-type organic semiconductor with unique alcohol solubility. Its favorable alcohol solubility even in the absence of polar side chains is mainly due to the large dipole moment and enhanced flexibility of the conjugated backbone once the boron atom is embedded. The p-π* conjugation directly affects the electronic structure as the LUMO is fully delocalized, including the boron atom, whereas the HOMO has the boron atom residing on a node. As a result, the molecule exhibits low-lying LUMO/HOMO energy levels of −3.61 eV/−5.73 eV paired with a good electron mobility of 1.37 × 10 −5 cm 2 V −1 s −1 . We further demonstrate its application as an electron acceptor in alcohol-processed organic solar cells (OSCs). To our best knowledge, this p-π* conjugated molecule is the first alcohol-processable non-fullerene electron acceptor, a feature that is in strong demand for environmentally friendly processing of OSCs.
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- Award ID(s):
- 1664975
- PAR ID:
- 10191587
- Date Published:
- Journal Name:
- Journal of Materials Chemistry C
- Volume:
- 7
- Issue:
- 24
- ISSN:
- 2050-7526
- Page Range / eLocation ID:
- 7427 to 7432
- Format(s):
- Medium: X
- Sponsoring Org:
- National Science Foundation
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- Free Publicly Accessible Full Text
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Accepted Manuscript1.0
- Journal Article:
- https://doi.org/10.1039/c9tc01562k
