A Photochemical Ligation System Enabling Solid‐Phase Chemiluminescence Read‐Out. Issue 54 (9th July 2019)

• Record Type: Journal Article
• Authors: Delafresnaye, Laura; Schmitt, Christian W.; Barner, Leonie; Barner‐Kowollik, Christopher
• Is Part Of: Chemistry. Volume 25:Issue 54(2019)
• Page Start: 12538
• Page End: 12544
• Publication Date: 2019-07-09
• Subjects: chemiluminescence -- fluorescence -- microsphere -- peroxyoxalate -- tetrazole; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201901858
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: The peroxyoxalate chemiluminescence (PO‐CL) reaction is among the most powerful and versatile techniques for the detection of hydrogen peroxide (H2 O2 ) and has been employed in various biological and chemical applications over the past 50 years. However, its two‐component nature (peroxyoxalate and fluorophore) limits its use. This contribution introduces an innovative and versatile photochemical platform technology for the synthesis of inherently fluorescent PO probes by exploiting the nitrile imine‐mediated tetrazole‐ene cycloaddition (NITEC) reaction. In the presence of hydrogen peroxide, the pioneered "2‐in‐1" molecule emits either yellow or blue light, depending on tetrazole (Tz) structure. Even in the absence of base, the emitted light remains visible and H2 O2 could be detected in the nanomolar range. Critically, the PO‐Tz can be readily incorporated into polymeric materials. As a first application of this promising material, a tailor‐made PO‐Tz is grafted on poly(divinylbenzene) (PDVB) particles to enable solid‐phase chemiluminescence on microspheres. Abstract : A versatile platform technology combining a fluorescent pyrazoline–peroxyoxalate adduct is introduced. Upon addition of hydrogen peroxide, the 2‐in‐1 molecule emits yellow or blue light that is visible to the naked eye. By judiciously selecting the tetrazole, this tailor‐made molecule can be readily incorporated into polymeric materials, enabling solid‐phase chemiluminescence read‐out.