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ORGANICLETTERS2004NewFluorescence-QuenchingProcessVol.6,No.19throughResumptionofPETProcess3301-3303InducedbyComplexationofAlkaliMetalIonJian-HuaBu,Qi-YuZheng,Chuan-FengChen,*andZhi-TangHuang*LaboratoryofChemicalBiology,CenterforMolecularScience,InstituteofChemistry,ChineseAcademyofSciences,Beijing100080,P.R.Chinahuangzt@public.bta.net.cnReceivedJune24,2004ABSTRACTUnderacidicconditions,afluorescence-quenchingprocessof1inducedbyselectivebindingofalkalimetalionswasdiscovered.Themechanismofthisnewprocessinvolvesalkalimetalion-induceddeprotonationoftheammoniumiontotriggerresumptionofafluorescence-quenchingPETprocess.ThePET(photoinducedelectrontransfer)signalprocesshassynthesizedanewfluorescentchemosensor1,whichhasabeenproventobeoneofthemostimportantmethodsforclassicalanthracene-methylene-amine-typefluorophore,fluorescentindicationinsupramolecularchemistryduetobutassembledinanuniqueway.Itsfluorescencecanbeitsuniqueadvantages,“allornone”switchability,guest-selectivelyquenchedbycomplexationofpotassiumorinduced“off-on”and“on-off”fluorescence,etc.1Itsrubidiumionunderacidicconditions.Thequenchingmech-applicationintherecognitionofalkalimetalionshasbeenanisminvolvesalkalimetalion-induceddeprotonationofwell-developed.OnerepresentativetypeofthesesensorshasammoniumiontotriggerresumptionofthePETprocess.ageneralunitofazacrown-spacer-fluorophore,inwhichAndtothebestofourknowledge,thisphenomenonhadanitrogenatomactsasboththereceptorinthecomplexationneverbeenreportedbefore.processandtheelectrondonorinthePETprocess.2However,Thesynthesisofhost1isillustratedinScheme1.Selectiveunderacidicconditions,thesignalfunctionisinvalidatednitrationof1,3-alternate-25,27-diethoxy-calix[4]crown-5(2),3+5duetotheprotonationoftheaminogroup.InspiredbytheanexcellentKionphore,withHNO3/HOAcgavemono-phenomenonofalkalimetal-inducedprotonejection,4we(3)(a)Ji,H.-F.;Dabestani,R.;Brown,G.M.J.Am.Chem.Soc.2000,(1)deSilva,A.P.;Gunaratne,H.Q.N.;Gunnlaugsson,T.;Huxley,A.122,9306-9307.
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