化学发光试剂的结构修饰及化学发光性能研究进展

穆小静夏之宁*(400030)35,*Email:[e-mail](2006DFA43520)(20775096)(CQCSTC2006BB5011)20080711,20080825,1,2,1,2ProgressinModificationsandLuminescentPropertiesofChemiluminescentCompoundsMuXiaojing,XiaZhining*(CollegeofChemistry&ChemicalEngineering,ChongqingUniversity,Chongqing400030)AbstractChemiluminescentassayshowingadvantagesofhighsensitivityandlowbackgroundissuitablefortraceanalysisforcomplexsystems.Thedevelopmentofnewchemiluminescentmoleculessuchasacridinium,luminol,peroxyoxalateandtheirderivativesand1,2dioxetaneisreviewed.KeywordsChemiluminescentcompounds,Acridiniums,Luminols,Peroxyoxalates,1,2Dioxetanes,,,,DodeigneKricka[1,2][3,4],,,,,,,:(1)(acridiniums);(2)(luminol);(3)(peroxyoxalate)(4)1,2(dioxetane)1,(1)195http:(emitter)X(leavinggroup)[5]:H2O29,,(X),,,(2),X(R3R4R5)X,,,,,,,,,R1R2X,XR1R2R3R4R51Scheme1Themolecularstructureofacridiniumestersandacridiniumsulfonamides2Scheme2Thechemiluminescentmechanismofacridiniumderivatives11(X1)(X2),,5%,,,;2005,,,[6]9(2,6())9(2,6)102,62,5,,2,6()2,6,2,6,,[7]9[2,64()]10Agiamarnioti[8],,9(3)1019620093http:[9]N9,[10]NN(4)9NN9Jiang[11],,,()[12,13]Sikorski9(2)10[14]9(2)10[15]9(2,6-)10[16]9(2)[17],,;,,;,12,90,,:1,3(3aR1=R2=CH3)[18];2(3bYY)[18,19,20];2(3c,R1=CH3OHOCH3OCH2PhOPO3,R2=H)2,7(3c2,7R1=R2=OCH3,(CH2)3SO3H[17~24])3Scheme3Acridiniumesterswithsidearmsa1,3;b2;c22,7,,,C2C7,,[21][21~25](RET)[24]1,32,72,;,[18~25]:!!N!9,,272,71,3,,,C∀N197http:(1R1=CH3),,1991,Batmanghelich[26]N(),10,90,Natrajan[21~25]N(1R1=),,,Sato[27]NNNNCH3,Mu[18]Weeks[28,29]10(3(N)),10(5(N))10(10(N)),NCH3,10,,10(3(N))10(5(N))10;10(10(N))[18]2(4a),,,(4b)(01%),,,N4N(ABENH)4,420nm515nm;ABENH2[30]Motoyoshiya[31],4(4c),,Neumann[32]52,31,4,2006Murthy[33],[1,8de][1,2]1,46,5(4d),;6,4(a);(b);(c)4;(d)Scheme4Themolecularstructureof(a)luminol;(b)isoluminol;(c)4styrylphthalhydrazides;(d)naphthodiazepinederivatives3(5a),,,,[34~40]19820093http:[41~45],,Stevanideng[34]2,2,22(5)1,3,24,5),1,2(5b)Silva[35]1,2,,Lee[37]1HNMRTCPOH2O2,,,1,11,2Lee[38](2,4)(DNPO);pHTCPO41,1(4)[39]Koike[40]((4)),,,Shamsipur:[41][42][43]5(35)2{(E)2[4(35)2]1}1[44]4,4[4,6(2)1,3,52]2,2[45](2,4,6)(TCPO)5(a);(b)1,2Scheme5Themolecularstructureof(a)peroxyoxalates;and(b)1,2dioxetanedione41,21,21,2,,,,,,201,2,()Matsumoto[46]1,2,1,2[47](6,OY,Ar,R1R2X,R3,A),,,61,2Scheme6Molecularstructureofnewchemiluminescent1,2dioxetanederivatives5McCapra[48]11,2(7a),,10,Hoshino[49,50]N(7b),;10,103,39,9(DMDSBA)[51]199http:[52]9,89(2)10,15~10,d(R=H)ef(R=SO2),6~108Scheme8Thepluralacridiniumemittersanditsleavinggroups6,,,,,,,20020093http:[1]CDodeigne,LThunus,RLejeuneTalanta,2000,51(3):415~439.[2]LJKricka.Anal.Chim.Acta,2003,500:279~286.[3]YYSu,HChen,ZMWangetal.Appl.Spectr.Rev.,2007,42(2):139~176.[4],,.,2007,20(1):124~128.[5]FMcCapra.Acc.Chem.Res.,1976,9(6):201~208.[6],,.,2008,26(4):257~264.[7],,.,2008,66:223~228.[8]KAgiamarnioti,TTriantis,KPapadopoulos.ActaChim.Slovenica,2004,51(1):67~76.[9]MAdamczyk,PGMattingly,JAMooreetal.Org.Lett.,2003,5(21):3779~3782.[10],,.,2007,26Suppl.:107~108.[11]QJiang,ANatrajan,DJSharpeetal.DE:60018758T,2006.[12]QJiang,ANatrajan,DJSharpeetal.US:2006202179,2006.[13]QJiang,ANatrajan,DJSharpeetal.US:2005032147,2005.[14]ASikorski,KKrzyminski,PMalechaetal.ActaCrystallog.SectionE,2007,63:O4484~U4984.[15]ASikorski,ANiziolek,KKrzyminskietal.ActaCrystallog.SectionE,2008,64:O372~U1731.[16]ASikorski,KKrzyminski,AKonitzetal.ActaCrystallog.SectionE,2005,61:O2131~O2133.[17]ASikorski,KKrzyminski,ABialonskaetal.ActaCrystallog.SectionE,2006,62:O555~O558.[18]XMu.Ph.DThesis,UniversityofWalesSwansea:Swansea(UK),2005.[19]FMcCapra,IBeheshti,HKoelling.US:5284951,1994.[20]FMcCapra.US:5283334,1994.[21]ANatrajan,QJiang,DSharpeetal.WO:2006130736A2,2006.[22]ANatrajan,QJiang,DSharpeetal.US:2005221390,2005.[23]ANatrajan,QJiang,DSharpeetal.US:2008014660,2008.[24]ANatrajan,TSells,HSchroederetal.US:2004063147A1,2004.[25]ANatrajan,TSells,HSchroederetal.EP:1403254A,2004.[26]SBatmanghelich,JSWoodhead,KSmithetal.J.Photochem.Photobiol.,1991,56A:249~253.[27]NSato.TetrahedronLett.,1996,37:8519~8522.[28]IWeeks,ARutter,ZLietal.US:2007166759,2007.[29]IWeeks,ARutter,ZLietal.GB:2405407,2005.[30]DFRoswell,EHWhite.MethodsEnzymol.,1978,57,409~423.[31]JMotoyoshiya,KYokota,TFukamietal.J.Heterocyclic.Chem.,2005,42(6):1063~1068.[32]HNeumann,SKlaus,MKlawonnetal.AbstractfromZeitschriftFurNaturforschungSectionB,2004,59(4):431~438.[33]NVKMurthy,ARReddy.AbstractfromIndianJ.Chem.B.,2006,45B:2512~2522.[34]CVStevaning,WJJBaader.Chem.ResearchS,2002(9):430~432.[35]SMSilva,FCasallanovo,KHOyamaguchietal.Luminescence,2002,17(5):313~320.[36]RBos,NWBarnett,GADysonetal.Anal.Chim.Acta,2004,502(2):141~147.[37]JHLee,JCRock,SBParketal.J.Chem.Soc.PerkinTransections,2,2002(4):802~809.[38]JHLee,JCRock,MASchlautmanetal.Chem.Soc.Perkin.Transections,2,2002,(10):1653~1657.[39]JHLee,JJe,JHuretal.Analyst,2003,128(10):1257~1261.[40]RKoike,YKato,JM