Synthesis of a novel pendant side-chain conjugated perylene based polymer

Syntese af en ny type sidekæde konjugeret perylen baseret polymer

Klitmøller, Nils Johannes

4. Term

Chemistry, Master (polyt)

2015

2015-10-02

56

Dette speciale undersøger, hvordan man kan fremstille en ny perylen-baseret monomer, der kan danne plastlignende materialer via radikal polymerisation. Målet var at lave homopolymerer med konjugerede sidekæder, som kan lægge sig tæt i lag (π–π-stabling) og dermed muligvis udvise fotovoltaiske egenskaber, dvs. omdanne lys til elektricitet. Monomeren blev syntetiseret i tre trin, efterfulgt af polymerisation som fjerde trin. Strukturen blev bekræftet med 1H NMR og ATR-FT-IR spektroskopi. Monomeren, polymeren og mellemprodukterne blev karakteriseret ved opløselighedstest, UV/Vis-absorbans og fluorescensspektroskopi samt samtidig termogravimetrisk analyse (opvarmning mens vægttab måles for at vurdere termisk stabilitet). Syntesen lykkedes og gav en kraftigt orange, fuldstændigt uopløselig homopolymer. Den lave opløselighed af flere mellemprodukter førte til, at der også blev fremstillet perylendiimider med fire forskellige alkylamin-substitutioner; den mest opløselige var diimiden af sec-butylamin. Forsøg på at føre disse diimider videre mod en tilsvarende homopolymer mislykkedes dog, fordi reaktiviteten i trin to – en Diels–Alder-cykloaddition med maleinsyreanhydrid – var kraftigt nedsat.

This thesis explores how to make a new perylene-based monomer that can be turned into a plastic-like material by radical polymerization. The aim was to produce homopolymers with conjugated side chains that can stack closely (π–π stacking), which may give photovoltaic behavior, i.e., the ability to convert light into electricity. The monomer was synthesized in three steps, followed by polymerization as the fourth step. Its structure was confirmed by 1H NMR and ATR-FT-IR spectroscopy. The monomer, polymer, and intermediates were characterized by solubility tests, UV/Vis absorption and fluorescence spectroscopy, and simultaneous thermogravimetric analysis (heating while measuring weight loss to assess thermal stability). The synthesis succeeded, yielding a bright orange homopolymer that was completely insoluble. Because several intermediates had low solubility, four perylene diimides with different alkylamine substitutions were also prepared; the sec-butylamine diimide was the most soluble. However, advancing these diimides toward a similar homopolymer was unsuccessful because step two—a Diels–Alder cycloaddition with maleic anhydride—showed severely reduced reactivity.

[This abstract was generated with the help of AI]

Solceller ; Organisk ; Polymer ; vinyl polymerisering ; Fotovoltaik ; Photovoltaics ; syntese ; OPV ; perylene

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