Lecture

Organic Electronics: Synthesis of Conjugated Molecules

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In course

MSE-486: Organic electronic materials

This course will introduce students to the field of organic electronic materials. The goal of this course is to discuss the origin of electronic properties in organic materials, charge transport mechanisms, chemical synthesis, materials processing, and dev ...

Description

This lecture covers the synthesis of conjugated molecules for organic electronics, focusing on classical and organometallic carbon bond forming reactions. It explains the mechanisms of palladium-catalyzed cross-coupling reactions, ligand dissociation, and oxidative addition. The lecture also delves into transmetalation, main group metals used in different name reactions, and the regioselectivity of reactions. Furthermore, it discusses the synthesis of poly(alkylthiophene)s, the dependence of molecular weight on conversion and stoichiometry, and the structure and properties of poly(thiophene)s. The lecture concludes with the band gap tuning of perylene bisimides through various reactions and the frontier orbital participation in Diels Alder reactions.

Instructor

Holger Frauenrath

Holger Frauenrath (born in Aachen, Germany) studied chemistry at RWTH Aachen , Germany from 1992 to 1997, with a focus on synthetic organic chemistry. He performed his PhD thesis from 1998 to 2001 in the research group of Prof Hartwig Höcker at RWTH Aachen, working on a project related to the stereospecific polymerization of methacrylates as well as their copolymerization with olefins using zirconocene catalysts. Holger Frauenrath then joined the group of Prof. Sam Stupp at Northwestern University , Evanston, IL, USA, as a postdoctoral fellow supported by a Feodor Lynen fellowship of the Alexander von Humboldt Foundation . His postdoctoral research projects were centered around the supramolecular self-assembly of rod-coil molecules. Holger Frauenrath returned to Germany in 2003 and started to build his own research group at FU Berlin, funded with an Emmy Noether Grant from the German Science Foundation . In 2005, the research group moved to the Department of Materials at ETH Zurich , Switzerland, where it became a scientifcally independent part of the Polymer Chemistry Group led by Prof. A. Dieter Schlüter . Holger Frauenrath obtained his Habilitation from ETH Zurich in 2009. In 2009, Holger Frauenrath has been appointed as a professor at the Institute of Materials (IMX) of the Ecole Polytechnique Federale de Lausanne (EPFL) , Switzerland, building the new Laboratory of Macromolecular and Organic Materials (LMOM) . In the same year, Holger Frauenrath was received the prestigious European Research Council (ERC) Starting Investigator grant.

Official source

Ontological neighbourhood

Chemistry

Organic chemistry: Organometallic chemistry

Related concepts (32)

Suzuki reaction

The Suzuki reaction is an organic reaction, classified as a cross-coupling reaction, where the coupling partners are a boronic acid and an organohalide and the catalyst is a palladium(0) complex. It was first published in 1979 by Akira Suzuki, and he shared the 2010 Nobel Prize in Chemistry with Richard F. Heck and Ei-ichi Negishi for their contribution to the discovery and development of palladium-catalyzed cross-couplings in organic synthesis. This reaction is also known as the Suzuki–Miyaura reaction or simply as the Suzuki coupling.

Main-group element

In chemistry and atomic physics, the main group is the group of elements (sometimes called the representative elements) whose lightest members are represented by helium, lithium, beryllium, boron, carbon, nitrogen, oxygen, and fluorine as arranged in the periodic table of the elements. The main group includes the elements (except hydrogen, which is sometimes not included) in groups 1 and 2 (s-block), and groups 13 to 18 (p-block).

Post-transition metal

The metallic elements in the periodic table located between the transition metals to their left and the chemically weak nonmetallic metalloids to their right have received many names in the literature, such as post-transition metals, poor metals, other metals, p-block metals and chemically weak metals. The most common name, post-transition metals, is generally used in this article. Physically, these metals are soft (or brittle), have poor mechanical strength, and usually have melting points lower than those of the transition metals.

Group 12 element

Group 12, by modern IUPAC numbering, is a group of chemical elements in the periodic table. It includes zinc (Zn), cadmium (Cd), mercury (Hg), and copernicium (Cn). Formerly this group was named IIB (pronounced as "group two B", as the "II" is a Roman numeral) by CAS and old IUPAC system. The three group 12 elements that occur naturally are zinc, cadmium and mercury. They are all widely used in electric and electronic applications, as well as in various alloys.

Stille reaction

The Stille reaction is a chemical reaction widely used in organic synthesis. The reaction involves the coupling of two organic groups, one of which is carried as an organotin compound (also known as organostannanes). A variety of organic electrophiles provide the other coupling partner. The Stille reaction is one of many palladium-catalyzed coupling reactions. Allyl, alkenyl, aryl, benzyl,acyl halides (Cl, Br, I), pseudohalides (OTf, OPO(OR)2), OAc The R1 group attached to the trialkyltin is normally sp2-hybridized, including vinyl, and aryl groups.

Related lectures (64)

Transition Metal Catalysis: Kumada Coupling

Explores the history and significance of the Kumada Coupling reaction in transition metal catalysis.

Synthesis of T-Conjugated Molecules

Covers the synthesis of T-conjugated molecules, cross-coupling reactions, polymerization, and band gap tuning.

V-Cross Couplings: Suzuki Stille Coupling

Covers the principles and mechanisms of V-cross couplings, focusing on Suzuki and Stille couplings.

Cross-Coupling of Organometallics

Covers versatile methods for C-C bond formation using different organometallic reagents and organic halides.

Retrosynthesis: Disconnections C-C