308255-23-4Relevant academic research and scientific papers
Reversible diastereoselective photocyclization of a diarylethene in a single-crystalline phase
Kodani,Matsuda,Yamada,Kobatake,Irie
, p. 9631 - 9637 (2000)
Optically active photochromic (S)- and (R)-1-(2-methyl-5-phenyl-3-thienyl)-2-[2-(3-methyl-1-penten-1-yl)-5-phenyl-3- thienyl]-3,3,4,4,5,5-hexafluorocyclopentenes ((S)-1a and (R)-1a) were synthesized. X-ray crystallographic measurement showed that (S)-1a a
Sensitive Assays by Nucleophile-Induced Rearrangement of Photoactivated Diarylethenes
Fredrich, Sebastian,Bonasera, Aurelio,Valderrey, Virginia,Hecht, Stefan
supporting information, p. 6432 - 6440 (2018/05/31)
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.
Light-Activated Sensitive Probes for Amine Detection
Valderrey, Virginia,Bonasera, Aurelio,Fredrich, Sebastian,Hecht, Stefan
supporting information, p. 1914 - 1918 (2017/02/05)
Our new, simple, and accurate colorimetric method is based on diarylethenes (DAEs) for the rapid detection of a wide range of primary and secondary amines. The probes consist of aldehyde- or ketone-substituted diarylethenes, which undergo an amine-induced decoloration reaction, selectively to give the ring-closed isomer. Thus, these probes can be activated at the desired moment by light irradiation, with a sensitivity that allows the detection of amines at concentrations as low as 10?6m in solution. In addition, the practical immobilization of DAEs on paper makes it possible to detect biogenic amines, such as cadaverine, in the gas phase above a threshold of 12 ppbv within 30 seconds.
