Research in our group focuses on the development of new materials for organic electronics, and in the understanding of how structure (planarity, different heteroatoms etc.) affects the properties of such materials in solution, in the solid state and as active materials in devices. For this purpose, we combine computational chemistry, organic synthesis, and materials characterization techniques. The research currently focuses on four main projects:
Helically-locked enantiopure twisted acenes.
The performance of organic electronic materials is strongly dependent on their conformation. Twisting these materials out of planarity induces chirality and thus results in new electronic, magnetic, optical and chiroptical properties with increasing numbers of applications as non-liner optical devices, spin filters, and magneto-optical devices. However, the effect of twisting is poorly understood, and often comes at the expense of π-conjugation, resulting in inferior device performance. We have recently introduced helically-locked twisted acenes, which allowing us to systematically study the effect of twisting on various electronic, optical and magnetic properties.
For more information, see: J. Am. Chem. Soc. 2018 140, 8086–8090.
The development of conducting polymers with strong emission in the visible and near infrared (NIR) spectral region.
While many conjugated polymers display strong emission at the visible spectral range, obtaining such emission in the NIR spectral region is a significant challenge. While oligo- and polyfurans present significantly stronger fluorescence than their thiophene analogs, they are yet to display fluorescence in the NIR. In addition, oligofurans suffer from low stability limiting their application. We have recently developed a new building unit, bifuranimide, which was significantly more stable than its furan analogs. Oligomers and polymers containing bifuran imide displayed strong fluorescence, from blue to red spectral region.
For more information, see: J. Mater. Chem. C 2018 6, 11951-11955.
Investigation of new macrocyclic systems.
We are investigating new macrocyclic systems for organic electronics based on oligofurans. In a computational study, we found that replacing thiophene with furan should significantly decrease the strain energies for small macrocycles. Calculations indicate that the macrocyclic ring should show low ionization potential, small reorganization energies, and small HOMO-LUMO gaps, rendering them as excellent candidates for organic semiconductors.
For more information, see: J. Org. Chem. 2018, 83, 3119-3125.
Development of new methodologies for the synthesis of conjugated backbones.
While conjugated oligomers such as oligophenylenes are important active materials in organic electronics, their synthesis can be challenging. We have recently introduced a regioselective transformation of oligofurans to oligoarenes using multiple Diels-Alder cycloadditions.
For more information, see: Angew. Chem. Int. Ed. 2017, 22, 16172-16177.