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EnglishUpon light-induced isomerization, diarylethenes (DAEs) equipped with reactive aldehyde moieties rearrange selectively in the presence of amines, accompanied by decoloration. In a comprehensive study, the probe structure was optimized with regard to its inherent reactivity in the nucleophile-triggered rearrangement reaction. Detailed structure-reactivity relationships could be derived, in particular with regard to the type of integrated (het)aryl moieties as well as the location of the formyl residue, and the probes' intrinsic reactivity with primary and secondary amines was optimized. Utilizing an ancillary base, the initially formed rearrangement product can engage in a subsequent catalytic cycle, leading to an amplified decoloration process. This additional catalytic pathway allows us to enhance the sensitivity of our method and successfully discriminate between amines and thiols. Moreover, probes that exhibit strong analyte-induced fluorescence modulation have been designed to further decrease the detection limit by using a more sensitive read-out. The optimized DAE probes are promising molecular components for future programmable sensing materials and devices.
| Data di pubblicazione: | 2018 |
| Titolo: | Sensitive Assays by Nucleophile-Induced Rearrangement of Photoactivated Diarylethenes |
| Autori: | |
| Citazione: | Fredrich, S., Bonasera, A., Valderrey, V., & Hecht, S. (2018). Sensitive Assays by Nucleophile-Induced Rearrangement of Photoactivated Diarylethenes. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 140(20), 6432-6440. |
| Rivista: | |
| Digital Object Identifier (DOI): | http://dx.doi.org/10.1021/jacs.8b02982 |
| Abstract: | Upon light-induced isomerization, diarylethenes (DAEs) equipped with reactive aldehyde moieties rearrange selectively in the presence of amines, accompanied by decoloration. In a comprehensive study, the probe structure was optimized with regard to its inherent reactivity in the nucleophile-triggered rearrangement reaction. Detailed structure-reactivity relationships could be derived, in particular with regard to the type of integrated (het)aryl moieties as well as the location of the formyl residue, and the probes' intrinsic reactivity with primary and secondary amines was optimized. Utilizing an ancillary base, the initially formed rearrangement product can engage in a subsequent catalytic cycle, leading to an amplified decoloration process. This additional catalytic pathway allows us to enhance the sensitivity of our method and successfully discriminate between amines and thiols. Moreover, probes that exhibit strong analyte-induced fluorescence modulation have been designed to further decrease the detection limit by using a more sensitive read-out. The optimized DAE probes are promising molecular components for future programmable sensing materials and devices. |
| URL: | http://pubs.acs.org/journal/jacsat |
| Appare nelle tipologie: | 1.01 Articolo in rivista |
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| File | Descrizione | Tipologia | Licenza | |
|---|---|---|---|---|
| B4_ja8b02982.pdf | Articolo principale | Post-print | Open Access Visualizza/Apri |
http://hdl.handle.net/10447/369201
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