Toward systems with extended conjugation in one- and two-dimensions and n-doped materials
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- Robert van Loon
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1 RIJKSUNIVERSITEIT GRONINGEN Design and synthesis of T-conjugated molecules Toward systems with extended conjugation in one- and two-dimensions and n-doped materials PROEFSCHRIFT ter verkrijging van het doctoraat in de W iskunde en Natuurwetenschappen aan de Rijksuniversiteit Groningen op gezag van de Rector Magnificus Dr. F. van der Woude in het openbaar te verdedigen op vrijdag 7 april 1995 des namiddags te 4.00 uur door Kornelis Lammert Pouwer geboren op 24 oktober 1964 te Musselkanaal
2 Promotores: Prof. Dr. E. W. Meijer Prof. Dr. R. M. Kellogg
3 Voonvoord Promoveren is een hele bevalling. Gelukkig hoef je het niet alleen te doen. Allereerst is er hulp en stimulans bij het uitvoeren van de experimenten, maar daarna ook, en dit is zeker niet onbelangrijk, bij het op papier zetten van de resultaten van die experimenten. Met het risico op het vergeten van mensen wil ik toch een aantal met name bedanken. Allereerst mijn promotoren. Prof. Dr. Wynberg voor de begeleiding tijdens de praktische jaren en voor de mogelijkheid van het opdoen van ervaring op andere synthetische terreinen by Syncom. Prof. Dr. Meijer voor het soepel ovememen van de begeleiding en de essentiele hulp gedurende de schrijffase. Prof. Dr. Kellogg voor het welwillend optreden als tweede promotor en de vlotte correctie van het manuscript. Bovendien wil ik Dr. Havinga bedanken voor de hulp bij de geleidingsmetingen en de stimulerende andere kijk op moleculen. De leden van de leescommissie, Prof. Dr. van Leusen, Prof. Dr. Feringa en Prof. Dr. Engberts ben ik erkentelijk voor de correctie van het manuscript. Verder ben ik dank verschuldigd aan Michiel Bouman, Auke Meetsma, Albert Kiewit en de heren van de analyse afdeling : Harm Draaijer, Jan Ebels en Jannes Hommes. Ton Vries wil ik bedanken voor de goede samenwerking binnen en buiten de chemie. In dit verband denk ik met name aan onze tijd in Eindhoven (een kamer met een tafel en twee matrassen), waar de oorsprong van dit boekje ligt. Voor het produceren van een proefschrift zijn de werkomstandigheden van bepalende invloed; alle bewoners van het organisch-lab (met name de A-poot) wil ik dan ook dan ook bedanken voor de rare (sterk relativerend of gewoon negatief?) maar toch we1 zeer plezierige sfeer. Het leven bestaat niet uit chemie alleen, het sociale aspect is zeker zo belangrijk voor het uiteindelijke resultaat. Vrienden die aan dit zeer plezierige gedeelte hebben bijgedragen, en dit nog steeds doen, wil ik hiervoor bedanken. Rest mij nog om mijn ouders te bedanken voor de geboden mogelijkheden en last maar zeker not least Gretha, zonder wie het toch we1 heel anders (en zeker niet beter) zou zijn gegaan.
4 This research was supported by the Dutch Ministry of Economic Affairs within the framework of Innovative Research Projects (IOP): Polymer Composites and Speciality Polymers.
5 Contents Chapter I 1.1 Introduction Synthesis of n-conjugated polymers Polythiophene Organometallic coupling Electrochemical synthesis Oxidative coupling Polypyrrole Polyaniline Other heterocyclic polymers Small Band Gab Polymers Fused Monomers Other Homopolymers Poly(parapheny1ene) Oxidative coupling Organometallic coupling Dehydrogenation of polycyclohexylenes Polyacetylene Shirakawa route The Luttinger route Precursor route Soluble polyacetylenes Polydiacetylenes Two-dimensional ladder structures Phenylene-heteroarene copolymers Direct polymerization Precursor route Oligomer polymerization Poly(ary1ene vinylene)~ Synthesis of well-defined oligomers Thiophene oligomers Other oligomers Aims of this thesis and survey of its contents Chapter 2 Design and synthesis of regioregular poly(dodecy1- [2.2'].bithienyl 2.1 Introduction Synthesis of regiorandom poly(3.dodecyl.[2,2'].bithienyl) Monomer synthesis Polymerization 43
6 2.3 Synthesis of regioregular poly(4.dodecyl.[2,2'].bithienyl) Monomer synthesis First approach Second approach Polymerization Absorption spectroscopy and thermochromism Discussion Concluding remarks Experimental section Chapter 3 Synthesis of well-defined oligomers and polymers containing thiophene. phenylene and pyrrole moieties using the Stetter reaction 3.1 Introduction The mechanisme of the Stetter reaction Oligomers Synthesis Absorption spectroscopy Discussion Polymers AA-BB-Polymerization Characterization AB-Polymerization Discussion Concluding remarks Experimental section Chapter 4 Design and synthesis of two-dimensional co-planar conjugated systems based on the pyrazine moiety 4.1 Introduction Synthesis of one-dimensional systems Model compounds Synthesis of two-dimensional systems Model compounds Oligomers Polymers Characterization Absorption spectroscopy X-ray analysis of compound Discussion Concluding remarks Experimental section
7 Chapter 5 Toward a stable n-doped conducting polymer 5.1 Introduction Synthesis of 1. 3.diketones Copper complex formation Keto-esters on both sides Mixed complexes Characterization Discussion Concluding remarks Experimental section 140 Samenvatting
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