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Synthesis of Electroactive Molecules Based on Benzodioxins and Tetrathiafulvalenes

<p>This thesis deals with the synthesis of electroactiveorganic compounds. The synthesis of ethylenedioxy-benzodioxinstri-dioxin and tetra-dioxin are described. These molecules wereprepared with the aim of creating donor molecules for cationicradical salts. The symmetric analogs of tri-dioxin,methylenedioxy-derivative and ethylenedioxy-naphthalene werealso synthesized. Three different cation radical salts with 2:1stoichiometries were obtained from tri-dioxin, whiletetra-dioxin merely provided polycrystalline materials.Tri-dioxin and tetra-dioxin were also successful as operationalmatrixes in PALDI-TOF.</p><p>Tetrathiafulvalenes with the2-dialkyl-amino-1,3-dithiolium-4-thiolate mesoion asbuilding-block was also synthesized. A series of doublyalkylthiol-substituted TTFs were prepared with the aim offorming self-assembly monolayers on gold surfaces in theapplication of organic thin film field-effect transistors.Film-formation for two TTFs were studied and they providedrelatively dense packed monolayers with a discrete distance ofthe TTF moiety from the gold surface.</p><p>The mesoionic compound was also for the first time used inan<i>umpolung</i>reaction. The electrophile obtained in situ bytreatment of mesoion with sulfuryl chloride was reacted with avariety of electron-rich aromatic compounds. From the receivedproducts three new arylthio-substituted TTFs weresynthesized.</p><p><b>Keywords:</b>Synthesis, Benzodioxin, Tetrathiafulvalene,Mesoion, Organic Conductor, Cation Radical Salt, CyclicVoltammetry, Electrocrystallization, Self-Assembly Monolayer,SAM, Organic Field-Effect Transistor, OFET</p>

Identiferoai:union.ndltd.org:UPSALLA/oai:DiVA.org:kth-3601
Date January 2003
CreatorsDahlstedt, Emma
PublisherKTH, Chemistry, Stockholm : Kemi
Source SetsDiVA Archive at Upsalla University
LanguageEnglish
Detected LanguageEnglish
TypeDoctoral thesis, comprehensive summary, text
RelationTrita-IOK, 1100-7974 ; 03:81

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