Summary of the technology
A new synthetic method to access precursors of linear polyacenes has been developed. The method allows for the preparation of hydrogenated polyacenes which are readily converted into the corresponding polyacene. Prepared materials are useful starting materials in the preparation of organic field effect transistors (OFETs), used in organic electronics. The method paves the way to the preparation of more efficient OFET components.
Description of the technology
Acenes are a class of polycyclic aromatic hydrocarbons consisting of planar sets of linearly fused benzene rings that have been the subject of extensive study due to their distinctive optoelectronic properties, which make them appealing materials for use in molecular electronic devices.Nonetheless, both the preparation and the application of extended acenes as functional materials are severely limited by their low stability, which diminish as the number of rings grows. Thus, heptacene has been only detected upon its in situ generation in a polymer matrix, whereas octacene and nonacene could be generated by using the photochemically induced bisdecarbonylation of the α-diketone precursors at 30K in an argon matrix. The synthesis of these precursors is far from trivial, requiring many steps and rather specialized techniques.
We have developed the first general synthesis of functionalized hydroacenes through a gold(I)-catalyzed cyclization of 1,7-enynes. This transformation allows the synthesis of non-substituted hydroacenes up to tetrahydrononacene in a highly modular manner in two steps. Remarkably, formation of the elusive nonacene has been achieved by dehydrogenation of stable tetrahydrononacene.
Our new approach has many of the characteristics of an ideal synthesis of this class of molecules, which could become readily available for industrial implementation:
- Our synthesis from commercially available aryl iodides and 1,7-enynes is highly modular.
- general and experimentally simple Pd-catalyzed coupling method.
- Our gold-catalyzed [4+2] intramolecular cycloaddition is also a very robust synthetic procedure that tolerates most functional groups and proceeds under very mild conditions.
- Hydroacenes obtained as final compounds are air stable and easily purified compounds than can be stored indefinitely under ordinary conditions.
The platform technology object of this application paves the way towards the preparation of shelf-stable precursors of large acenes and new polyaromatic hydrocarbons (PAHs). Such compounds find applications in organic electronics, more particularly in Organic Field Effect Transistors (OFETs) or as semiconductors, or in environmental chemistry, for the monitoring of air pollution with PAHs as standards in analytical methods. The global market for end-user products containing organic electronic components is expected to be worth $75 billion by 2020, while experiencing an impressive CAGR of 29%. The most popular acenes in organic electronics are tetracene, pentacene, and rubrene. Each of these components is being used industrially for the manufacture of devices, in particular with electroluminescent properties.
Current development status
preparation of OFETs
Desired business relationship
New technology applications
Other : joint R&D (e.g. custom synthesis of acenes)
Intellectual property status
Patent already applied for
Institute of Chemical Research of Catalonia
Technology Transfer Office
Additional information (attached documents)