Gesteuerte Reaktionsorthogonalität in der Polymer‐ und Materialwissenschaft

Wirs tellen eine wellenlängengesteuerte Syntheseroute zu Phenalendiimiden vor.Z wei aufeinanderfolgende Diels-Alder-Reaktionen von Methylisophthalaldehyden und Maleimiden ergeben Hexahydrophenalen-1,6-dioldiimide über 5-Formylhexahydrobenzo[f]isoindole als Intermediat. Beide Photoreaktionen sind hoche ffizient (82-99 %A usbeute) und weisen eine hohe Diastereoselektivitäta uf (62-98 %d.r.). Die Kontrolle der aufeinanderfolgenden Additionsreaktionen über die Wellenlänge ermçglicht die baukastenartige Konstruktion von Phenalendiimid-Gerüsten aus einfachen Bausteinen. Damit erçffnet diese Synthesemethode einen einfachen Zugang zu einer neuen Klasse von stabilen Phenalenyldiimid-Neutralradikalen.

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Wellenlängengesteuerte photochemische Synthese von Phenalendiimiden

Feist

Walden²,

Alves³

et al. 2021

Angewandte Chemie

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Wavelength‐Selective Photopolymerization of Hybrid Acrylate‐Oxetane Liquid Crystals

et al. 2021

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We report on the wavelength‐selective photopolymerization of a hybrid acrylate‐oxetane cholesteric liquid crystal monomer mixture. By controlling the sequence and rate of the orthogonal free‐radical and cationic photopolymerization reactions, it is possible to control the degree of phase separation in the resulting liquid crystal interpenetrating networks. We show that this can be used to tune the reflective color of the structurally colored coatings produced. Conversely, the structural color can be used to monitor the degree of phase separation. Our new photopolymerization procedure allows for structuring liquid crystal networks in three dimensions, which has great potential for fabricating liquid crystal polymer materials with programmable functional properties.

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Photo Click Reaction of Acylsilanes with Indoles

2021

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Light‐mediated coupling of acylsilanes with indoles is reported. This photo click reaction occurs under mild conditions (415 nm) mostly in quantitative yield and provides stable silylated N,O‐acetals via light mediated siloxycarbene generation with subsequent indole‐N‐H insertion. We show that this very efficient and fully atom economic coupling process can be applied to conjugate complex systems, as documented by the clicking of carbohydrates with indole alkaloids. The method is also applicable to the conjugation of polymer chains. The linking acetal moiety can be readily cleaved and it is also shown that wavelength‐selective coupling and cleavage with acyl silanes bearing a second photoactive moiety is possible. This is documented by a successful polymerization/depolymerization sequence and by a polymer folding/unfolding process.

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Gesteuerte Reaktionsorthogonalität in der Polymer‐ und Materialwissenschaft

Abstract: Die ORCID-Identifikationsnummer(n) fürden/dieA utor(en)d ieses Artikels findet man unter

Cited by 7 publications

References 303 publications

Wellenlängengesteuerte photochemische Synthese von Phenalendiimiden

Wellenlängengesteuerte photochemische Synthese von Phenalendiimiden

Wavelength‐Selective Photopolymerization of Hybrid Acrylate‐Oxetane Liquid Crystals

Photo Click Reaction of Acylsilanes with Indoles

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