Institute of Chemical Research of Catalonia

Method for the preparation of linear polyacenes and building blocks of organic electronic components.

Posted by Institute of Chemical Research of CataloniaResponsive · Patents for licensing · Spain

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.

Institute of Chemical Research of Catalonia

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

Experimental technologies

Applications

preparation of OFETs

Applications

organic electronics

Desired business relationship

Patent licensing

Technology development

New technology applications

Other : joint R&D (e.g. custom synthesis of acenes)

Intellectual property status

Patent already applied for
PCT/EP2017/050676
PCT

Technology Owner

Institute of Chemical Research of Catalonia

Technology Transfer Office

Additional information (attached documents)

Related keywords

  • Electronics, Microelectronics
  • Industrial Technologies
  • Chemical Technology and Engineering
  • Organic Substances
  • Semiconductors Market

About Institute of Chemical Research of Catalonia

Technology Transfer Office from Spain

The Institute of Chemical Research of Catalonia represents one of the very first fruits of the new scientific policy of the government of Catalonia (Spain) aimed at creating new research centres in strategic areas. ICIQ, in particular, has been created with the ambition of becoming a reference for chemistry in the European Research Space.

Our society faces important challenges in the XXI century, among which health and environmental concerns are of outmost importance. Chemistry will play an essential role in both of these challenges. To succeed, our increasingly knowledge-based economy will require a solid and strong chemical industry; currently 150.000 jobs in Catalonia (and more than 2 million in the EU) directly arise from the chemical industry. In order for this industry to be successful in the future, it must take a sustainable approach based on the rational use of feed-stocks and raw materials. For this, fundamental chemical research needs to be funded and novel approaches into transforming matter must be developed.

We at ICIQ consider that catalysis is the key activity for sustainable chemistry. Catalytic processes can minimize raw materials and energy consumption, and can lead to the selective formation of target products with minimal generation of wastes. In line with this consideration, we have taken catalysis as one of our main research topics.

Complementary to our research focus, attention has been paid to the development of a simple and efficient organizational model for ICIQ, able to overcome known difficulties normally associated with larger and more traditional research institutions. The Institute of Chemical Research of Catalonia aims at bridging the gap between academic research and industry, focusing its research on catalytic chemical processes for applications in health, energy and sustainability.

At ICIQ, we consider that patents are highly efficient, safe and solid tools to provide protection from competitors. This is why we file patents for our in-house developed-technologies: to give our co-development projects with industry a strong starting IP position. As a research centre our goal is always to co-develop our technology adapting it to the industrial partner’s specific needs and ultimately transfer the technology to this company, with a flexible licensing strategy adapted to each case.

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