A master thesis from Aalborg University
Synthesis of a novel pendant side-chain conjugated perylene based polymer
[Syntese af en ny type sidekæde konjugeret perylen baseret polymer]
Author(s)
Term
4. Term
Education
Publication year
2015
Submitted on
2015-10-02
Pages
56 pages
Abstract
Fokuspunkterne i dette speciale var at udvikle en syntese-strategi for en ny type perylen baseret monomer, til radikale polymerisering. Den resulterende homopolymer med side-kæde konjugerede systemer har potentielle fotovoltaiske egenskaber via p-p kobling mellem enhederne. Monomeren blev syntetiseret gennem en 3-trins proces, efterfulgt af fjerde trin; polymerisering. Verificering af strukturen forløb vha. 1H NMR og ATR FT-IR-spektroskopi. Karakterisering af polymeren og mellemstadier inkluderede opløseligheds bestemmelse, UV/VIS absorbans og fluorescens spektroskopi og simultan termogravimetrisk analyse. Syntesen lykkedes, hvilket resulterede i en uopløselig lys orange polymer. Den lave opløselighed af mellemprodukterne førte til yderligere syntese af perylen-diimider med fire forskellige alkylamin substituenter, den mest opløselige af slagsen var diimiden af sec-butylamin. Videre syntese af diimiderne mod en tilsvarende homopolymer fejlede dog, på grund af den stærkt reducerede reaktivitet i Diels-Alder cycloadditionen af maleinsyreanhydrid, i trin to.
The focus in this master thesis was developing a synthetic strategy for a novel perylene based monomer, capable of radical polymerization, resulting in side-chain conjugated homopolymers with possible photovoltaic properties, by p-p stacking of conjugated pendants. The monomer was synthesized through a 3-step process, followed by the fourth step, i.e., polymerization. Verification of the structure was done by 1H NMR and ATR FT-IR spectroscopy, and characterization of the polymer and intermediates included solubility analysis, UV/VIS absorbance and fluorescence spectroscopy and simultaneous thermogravimetric analysis. The synthesis was successful, resulting in a completely insoluble bright orange homopolymer. The low solubility of the intermediates led to the additional synthesis of perylene diimides with four different alkylamine substitutions, the most soluble of which was the diimide of sec-butylamine. Further synthesis of the diimides towards a similar homopolymer was however unsuccessful, due to the severely reduced reactivity in the Diels-Alder cycloaddition of maleic anhydride, in step two.
Keywords
Solceller ; Organisk ; Polymer ; vinyl polymerisering ; Fotovoltaik ; Photovoltaics ; syntese ; OPV ; perylene
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