Functionalization of BN-Pyrenes/Phenanthrenes andIncorporation into Organic Materials

• Applicant: Dr. Benedikt Neue
• Subject Area: Organic Molecular Chemistry - Synthesis and Characterisation
• Term: from 2012 to 2013
• Project identifier: Deutsche Forschungsgemeinschaft (DFG) - Project number 217572453

Polycyclic aromatic hydrocarbons (PAHs) such as pyrenes possess unique photophysical and electronic properties. There are numerous examples for PAHs in the literature containing exclusively carbon-carbon (C-C)-bonds. These compounds are very useful in the field of material sciences for example as organic light-emitting devices and field-effect transistors. In order to alter and tune the properties of such pi-conjugated systems for application, incorporation of main group elements into the framework as well as modifications by introduction of various substituents at the periphery can be useful. Recently systems in which an internal carbon-carbon (C-C)-fragment is exchanged by a boron-nitrogen (B-N)- unit in the pi-conjugated framework were introduced. This transformation leads to remarkable changes in the electronic and photophysical properties of these systems compared to the all-carbon analogues. Until now examples of PAHs containing internal BN units in place of CC are rare, there are only a few structural motifs known. Due to their attractive properties the design and synthesis of novel functionalized, dimeric and polymeric systems based on BN-containing heterocycles - especially with pyrene and phenanthrene frameworks - is an interesting objective in view of materials science.At first the research project will focus on structured reactivity-studies of BN-pyrenes and phenanthrenes to investigate the accessibility of possible starting materials for the synthesis of large systems. Second the work will concentrate on the development and use of straightforward synthetic strategies as well as various precursor molecules to prepare and functionalize BN-pyrenes/phenanthrenes in view of application in materials science. Pathways for the synthesis of extended dimeric or polymeric networks are proposed.

• DFG Programme: Research Fellowships
• International Connection: Canada
• Host: Professor Warren E. Piers, Ph.D.