Mechanically induced chemiluminescence from polymers incorporating a 1,2-dioxetane unit in the main chain

• Published in: Nature chemistry 2012-06, Vol.4 (7), p.559-562
• Main Authors: Chen, Yulan, Spiering, A. J. H., Karthikeyan, S., Peters, Gerrit W. M., Meijer, E. W., Sijbesma, Rint P.
• Format: Article
• Language: English
• Subjects: 639/638/455; Adamantane - analogs & derivatives; Adamantane - chemistry; Adhesion; Analytical Chemistry; Biochemistry; Chemiluminescence; Chemistry; Chemistry and Materials Science; Chemistry/Food Science; Decomposition; Emissions; Energy Transfer; Heterocyclic Compounds - chemistry; Inorganic Chemistry; Light; Luminescence; Luminescent Measurements; Organic Chemistry; Physical Chemistry; Polymers; Polymers - chemistry; Polymethacrylic Acids - chemistry
• ISSN: 1755-4330; 1755-4349
• DOI: 10.1038/nchem.1358

Nature uses mechanochemical transduction processes to achieve diverse and vital functions, such as hearing, cellular adhesion and gating of ion channels. One fascinating example of biological mechanotransduction is the emission of light on mechanical stimulation. However, molecular-level transduction of force into luminescence in a synthetic system remains a challenge. Here, we show that bis(adamantyl)-1,2-dioxetane emits visible light when force is applied to a polymer chain or network in which this unit is incorporated. Bright-blue luminescence was observed on sonication of solutions of dioxetane-containing linear polymers and on the straining of polymer networks with dioxetane crosslinkers. Light is emitted from the adamantanone-excited state that forms on opening of the four-membered dioxetane ring. Increased sensitivity and colour tuning were achieved by energy transfer to suitable acceptors. High spatial and temporal resolutions highlight the potential to study the failure of polymeric materials in unprecedented detail. Bisadamantyl 1,2-dioxetane is a luminescent mechanophore that, when incorporated into polymer chains or networks, emits visible light when its 4-membered ring is opened by sonication in solution or by deformation of a bulk sample. This phenomenon mimics biological mechanoluminescence and highlights the potential to study the failure of polymeric materials with high spatial and temporal resolution.