Enhancement effect on the chemiluminescence of acridinium esters under neutral conditions

Abstract

Enhancement effect on the chemiluminescence of acridinium ester derivatives under neutral conditions was investigated. Additions of phenols did not enhance the chemiluminescence intensities of acridinium ester derivatives in the presence of horseradish peroxidase and hydrogen peroxide. Additions of cetyltrimethylammonium bromide apparently enhanced the chemiluminescence intensities of phenyl 10-methyl-10λ -acridine-9-carboxylate derivatives with electron-withdrawing groups at the 4-position of the phenyl group. In particular, the chemiluminescence intensity of 4-(trifluoromethyl)phenyl 10-methyl-10λ -acridine-9-carboxylate trifluoromethanesulfonate salt was 5.5 times stronger in the presence of cetyltrimethylammonium bromide than in its absence at pH 7. The chemiluminescence intensity of 3,4-dicyano-phenyl 10-methyl-10λ -acridine-9-carboxylate trifluoromethanesulfonate salt was 46 times stronger in the presence of cetyltrimethylammonium bromide at pH 7 than in its absence at pH 10.

Prevent or Cure—The Unprecedented Need for Self‐Reporting Materials

“…[124,[126][127][128][129][130] Therefore,CLreactions find widespread applications in biomedical or analytical fields with ongoing research for persistent improvement. However,the challenge to gain higher CL quantum yields,tune the emission range,or simplify the CL system is to modify the reaction environment or the luminophore itself in such away that the CL properties are not diminished accidentally.Nevertheless,recent research into common luminophores,s uch as dioxetanes, [131,132] peroxyoxalates (POs), [122,[133][134][135][136][137] acridinium esters, [138][139][140][141] luminol, [129,142] and their respective derivatives,led to the development of aplethora of advanced, promising self-reporting CL systems.T he CL of acridinium esters,f or example,c an be triggered by antioxidants,e nzymes or peroxides and thus finds application in (biomedical) analytics as self-reporting sensor for these substances. [138][139][140][141] In the presence of atrigger, the acridinium esters are oxidized to dioxetanones,w hich decompose with the release of CO 2 to form the highly emissive 10-methyl-9-acridone, [139,143] as displayed in Scheme 2A.S of ar, alkaline conditions were required for the CL emission of acridinium esters.H owever,r ecently,a cridinium ester derivatives were synthesized which allow the CL reaction to proceed under neutral conditions.T his was achieved by introducing electron withdrawing groups (e.g.…”

Vorbeugen oder Heilen – die beispiellose Notwendigkeit von selbstberichtenden Materialien

“…Die Herausforderung,h çhere CL-Quantenausbeuten zu erzielen, den Emissionsbereich einzustellen oder das CL-System zu vereinfachen, besteht jedoch darin, die Reaktionsumgebung oder den Luminophor selbst so zu modifizieren, dass die CL-Eigenschaften nicht versehentlich vermindert werden. Nichtsdestotrotz führte die aktuelle Forschung an bekannten Luminophoren wie Dioxetanen, [131,132] Peroxyoxalaten (POs), [122,[133][134][135][136][137] Acridiniumestern, [138][139][140][141] Luminol [129,142] und deren jeweiligen Derivaten zur Entwicklung einer Fülle an fortschrittlichen, vielversprechenden selbstberichtenden CL-Systemen. Die CL von Acridiniumestern beispielsweise kann durch Antioxidantien, Enzyme oder Peroxide ausgelçst werden und findet daher in der (biomedizinischen) Analytik als selbstberichtender Sensor fürd iese Stoffe Anwendung.…”

“…Die CL von Acridiniumestern beispielsweise kann durch Antioxidantien, Enzyme oder Peroxide ausgelçst werden und findet daher in der (biomedizinischen) Analytik als selbstberichtender Sensor fürd iese Stoffe Anwendung. [138][139][140][141] In der Gegenwart eines Auslçsers werden die Acridiniumester zu Dioxetanonen oxidiert, die sich durch die Freisetzung von CO 2 in das stark emittierende 10-Methyl-9acridon zersetzen, [139,143] wie in Schema 2d argestellt. Bislang waren fürd ie CL-Emission von Acridiniumestern alkalische Bedingungen erforderlich.…”

“…[139] Auch die Zugabe von Cetyltrimethylammoniumbromid führte zu einer erhçhten CL solcher Acridiniumesterderivate. [140] Ebenso eignen sich Peroxyoxalat (PO)-Luminophore ideal fürA nalysemethoden in der Lebensmittel-und Umweltanalyse,S ensortechnik, Pharmakologie,B iologie oder Medizin. [122,135,136] Wiebei den Acridiniumestern kann die CL-Reaktion von POs durch verschiedene aktive Spezies wie Peroxide,M ikroorganismen, Glucose,T oxine oder Antioxidantien induziert werden.…”

Cationic and Betaine-Type Boronated Acridinium Dyes: Synthesis, Characterization, and Photocatalytic Activity

“…23 Furthermore, selected derivatives exhibit potent chemiluminescence, making them useful in clinical diagnostics. 24−26 Among various compounds comprising acridine scaffold, cationic acridinium dyes feature the reactive 9-position which has been exploited in designing dynamic supramolecular systems 27,28 as well as for pseudobase formation. 29,30 Recently, photocatalytic properties of selected acridinium dyes with a special emphasis on 9-mesitylacridinium derivatives were discovered.…”