Conjugated Organic Materials

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Outline Curriculum (5 lectures) Each lecture  45 minutes

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Presentation transcript:

Conjugated Organic Materials Nobel Prize 2000: Shirakawa, Heeger, MacDiarmid Applications: Batteries Antistatic & Electrochromic Coatings Plastic Electronics Sensors, etc Konarka Sony

Conductivity in Polymers Insulating Polymers / Semiconductors / Synthetic Metals Electrical conductivity / Ionic conductivity Metals Silver Copper Aluminum 102 to 1010 S /cm Graphite Polyacetylene Poly(p-phenylene vinylene) Silicon (10-4) Aqueous salt solutions (ca. 1) Semiconductors Doping 10-5 to 102 S /cm PEO / LiOTf (10-8) Glass Polyethylene Polystyrene Insulators 10-15 to 10-5 S /cm

Band Theory CB VB Medium-sized molecule Large sized molecule Diatomic Separate atoms Antibonding orbital CB Band gap VB Bonding orbital Effect on Optical Properties and Ability to Generate Charge Carriers (Doping)

Band Gaps in Common Conjugated Polymers Conducting Polymer Band Gap trans-Polyacetylene (PAc) 1.4 eV Polythiophene (PTh) 2.1 eV Poly(p-phenylene vinylene) (PPV) 2.5 eV Intrinsically non-conductive polymers !

Synthetic Aspects Oxidative Polymerization (electrochemical / chemical) Example: Polythiophenes, polypyrrole, polyaniline Polymerization through organo- metallic coupling reactions Example: Polythiophenes, polypyrrole, PPV Polymer Modification Example: PPV derivatives Stille Coupling; Suzuki-Miyaura Coupling; etc

GRIM Process for the Synthesis of Regioregular Poly(3-alkylthiophene)s An Example of a Living Condensation Polymerization Process R group ends up at polymer chain end First Step: Conversion of dibromothiophene to Grignard Species Second Step: Catalytic process (Kumada coupling) Third Step: In our case hydrolysis; also possible to react with a second Grignard species

GRIM Mechanism

Applications h+ e - Coatings: Polypyrrole, Polythiophenes Antistatic coatings, fibers polypyrrole, PEDOT (BaytronTM) Anticorrosive coatings polypyrrole Electrochromic Windows polythiophenes Electronic Devices: PPV, Polythiophenes Polymer Light Emitting Diodes (PLEDs) Field-Effect Transistors Photovoltaics (combination with fullerenes) Sensors: functionalized PPV, polythiophene derivatives, polyaniline Mg:Ag Cathode e - Conjugated Polymer h+ ITO Anode Transparent Cover hn Swager et al., Chem Rev. 2000, 2537.