Recognition of Anions PDF
Preview Recognition of Anions
129 Structure and Bonding SeriesEditor:D.M.P.Mingos EditorialBoard: P.Day·X.Duan·L.H.Gade·T.J.Meyer G.Parkin·J.-P.Sauvage StructureandBonding SeriesEditor:D.M.P.Mingos RecentlyPublishedandForthcoming Volumes ContemporaryMetalBoronChemistryI Non-CovalentMulti-PorphyrinAssemblies VolumeEditors:Marder,T.B.,Lin,Z. SynthesisandProperties Vol.130,2008 VolumeEditor:Alessio,E. Vol.121,2006 RecognitionofAnions VolumeEditor:Vilar,R. RecentDevelopmentsinMercuryScience Vol.129,2008 VolumeEditor:Atwood,DavidA. Vol.120,2006 LiquidCrystallineFunctionalAssemblies andTheirSupramolecularStructures LayeredDoubleHydroxides VolumeEditor:Kato,T. VolumeEditors:Duan,X.,Evans,D.G. Vol.128,2008 Vol.119,2005 OrganometallicandCoordinationChemistry SemiconductorNanocrystals oftheActinides andSilicateNanoparticles VolumeEditor:Albrecht-Schmitt,T.E. VolumeEditors:Peng,X.,Mingos,D.M.P. Vol.127,2008 Vol.118,2005 HalogenBonding MagneticFunctionsBeyond FundamentalsandApplications theSpin-Hamiltonian VolumeEditors:Metrangolo,P.,Resnati,G. VolumeEditor:Mingos,D.M.P. Vol.126,2008 Vol.117,2005 HighEnergyDensityMaterials IntermolecularForcesandClustersII VolumeEditor:Klapötke,T.H. VolumeEditor:Wales,D.J. Vol.125,2007 Vol.116,2005 Ferro-andAntiferroelectricity IntermolecularForcesandClustersI VolumeEditors:Dalal,N.S., VolumeEditor:Wales,D.J. Bussmann-Holder,A. Vol.115,2005 Vol.124,2007 SuperconductivityinComplexSystems PhotofunctionalTransitionMetalComplexes VolumeEditors:Müller,K.A., VolumeEditor:V.W.W.Yam Bussmann-Holder,A. Vol.123,2007 Vol.114,2005 Single-MoleculeMagnets PrinciplesandApplications andRelatedPhenomena ofDensityFunctionalTheory VolumeEditor:Winpenny,R. inInorganicChemistryII Vol.122,2006 VolumeEditors: Kaltsoyannis,N.,McGrady,J.E. Vol.113,2004 Recognition of Anions Volume Editor: Ramón Vilar Withcontributionsby P.Ballester·G.W.Bates·S.R.Bayly·P.D.Beer·S.L.Ewen P.A.Gale·I.Hamachi·J.H.G.Steinke·S.Tamaru·R.Vilar 123 The series Structure and Bonding publishes critical reviews on topicsof research concerned with chemicalstructureandbonding.ThescopeoftheseriesspanstheentirePeriodicTable.Itfocuses attentiononnewanddevelopingareasofmodernstructuralandtheoreticalchemistrysuchasna- nostructures,molecularelectronics,designed molecularsolids,surfaces,metalclustersandsupra- molecularstructures.Physicalandspectroscopictechniquesusedtodetermine,examineandmodel structuresfallwithin thepurviewofStructureandBondingtotheextent thatthefocusisonthe scientificresultsobtainedandnotonspecialistinformationconcerningthetechniquesthemselves. Issuesassociatedwiththedevelopmentofbondingmodelsandgeneralizationsthatilluminatethe reactivitypathwaysandratesofchemicalprocessesarealsorelevant. Asarule,contributionsarespeciallycommissioned.Theeditorsandpublisherswill,however,always bepleasedtoreceivesuggestionsandsupplementaryinformation.PapersareacceptedforStructure andBondinginEnglish. InreferencesStructureandBondingisabbeviatedStructBondandiscitedasajournal. SpringerWWWhomepage:springer.com VisittheStructBondcontentatspringerlink.com ISBN978-3-540-79091-4 e-ISBN978-3-540-79092-1 DOI10.1007/978-3-540-79092-1 StructureandBondingISSN0081-5993 LibraryofCongressControlNumber:2008923960 (cid:1)c 2008Springer-VerlagBerlinHeidelberg Thisworkissubjecttocopyright.Allrightsarereserved,whetherthewholeorpartofthematerial isconcerned,specificallytherightsoftranslation,reprinting,reuseofillustrations,recitation,broad- casting,reproductiononmicrofilmorinanyotherway,andstorageindatabanks.Duplicationof thispublicationorpartsthereofispermittedonlyundertheprovisionsoftheGermanCopyrightLaw ofSeptember9,1965,initscurrentversion,andpermissionforusemustalwaysbeobtainedfrom Springer.ViolationsareliabletoprosecutionundertheGermanCopyrightLaw. Theuseofgeneraldescriptivenames,registerednames,trademarks,etc.inthispublicationdoesnot imply, even in the absence of a specific statement, thatsuchnamesareexempt fromthe relevant protectivelawsandregulationsandthereforefreeforgeneraluse. Coverdesign:WMXDesignGmbH,Heidelberg TypesettingandProduction:le-texpublishingservicesoHG,Leipzig Printedonacid-freepaper 9876543210 springer.com SeriesEditor Prof.D.MichaelP.Mingos Principal St.EdmundHall OxfordOX14AR,UK [email protected] VolumeEditor Dr.RamónVilar ImperialCollegeLondon DepartmentofChemistry SouthKensington London,SW72AZ,UK [email protected] EditorialBoard Prof.PeterDay Prof.ThomasJ.Meyer DirectorandFullerianProfessor DepartmentofChemistry ofChemistry CampusBox3290 TheRoyalInstitutionofGreatBritain VenableandKenanLaboratories 21AlbermarleStreet TheUniversityofNorthCarolina LondonW1X4BS,UK andChapelHill [email protected] ChapelHill,NC27599-3290,USA [email protected] Prof.XueDuan Prof.GerardParkin Director StateKeyLaboratory DepartmentofChemistry(Box3115) ofChemicalResourceEngineering ColumbiaUniversity BeijingUniversityofChemicalTechnology 3000Broadway 15BeiSanHuanDongLu NewYork,NewYork10027,USA Beijing100029,P.R.China [email protected] [email protected] Prof.Jean-PierreSauvage Prof.LutzH.Gade FacultédeChimie Anorganisch-ChemischesInstitut LaboratoiresdeChimie UniversitätHeidelberg Organo-Minérale ImNeuenheimerFeld270 UniversitéLouisPasteur 69120Heidelberg,Germany 4,rueBlaisePascal [email protected] 67070StrasbourgCedex,France [email protected] StructureandBonding AlsoAvailableElectronically For all customers who have a standing order to Structure and Bonding, we offer the electronic version via SpringerLink free of charge. Please contact yourlibrarianwhocanreceiveapasswordorfreeaccesstothefullarticlesby registeringat: springerlink.com Ifyoudonothaveasubscription,youcanstillviewthetablesofcontentsofthe volumesandtheabstractofeacharticlebygoingtotheSpringerLinkHome- page,clickingon“BrowsebyOnlineLibraries”,then“ChemicalSciences”,and finallychooseStructureandBonding. Youwillfindinformationaboutthe – EditorialBoard – AimsandScope – InstructionsforAuthors – SampleContribution atspringer.comusingthesearchfunction. Color figures are published in full color within the electronic version on SpringerLink. Preface Alargenumberofbiologicallyrelevantspeciesarenegativelycharged,there- foreit is not surprising that nature has developed sophisticated receptors to recognise,detectandtransformanions.Forexample,complexreceptorssuch as phosphate- and sulphate-binding proteins are employed by living cells to selectively recognise these two geometrically analogous anions. In addition to their roles in biological systems, some anions also have important envi- ronmentalimpacts.Forexample,cyanide,pertechnetateandchromatespose serioushealthproblemsifpresentinwatersupplies. Because of their important biological roles and potential environmental impact there is great current interest in developing molecular receptors to selectivelyrecogniseanionsandindoingsobeabletosequester,transformor sensethem.Thesixchapterspresentedinthisvolumeprovideanoverviewof anion recognition and the most recent advances in this fast-growingarea of supramolecularchemistryarehighlighted. ThefirstchapterbyBatesandGaleprovidesanoverviewofthecoordination ofanionsbysyntheticorganichosts.Thedifferentorganicfunctionalgroups used to bind anions are presented and this provides an introduction to the structuralandelectronicpropertiesthathostsmusthavetorecogniseanionic guests.Ontheotherhand,BaylyandBeergiveadetailedaccountoftheuseof metalcomplexesasanionreceptors.Besidestheimportantstructuralfeatures that metals can confer to receptors, their optical and redox properties make themattractiveforthedevelopmentofanionsensors. Metal-based receptors have found particularly interesting applications in therecognitionofphosphorylatedspeciesofbiologicalinterest(e.g.phospho- rylatedaminoacidsandpeptides). ThisareaisreviewedindepthbyTamaru and Hamachi with particular emphasis on a series of receptors based on zinc(II) centres which have been shown to bind phosphates with very high bindingconstantsinaqueousmedia.Theapplicationsofthistypeofreceptor forthedetectionofsamplesofbiologicalinterestarealsopresented. Ballester provides an interesting account of anion···π interactions and theirimpactinhostdesign.Overthepastfewyearstherehasbeenmounting evidencethatthistypeofinteractionplaysanimportantroleinanionrecog- nition. The chapter startswithadetailed overview ofthe theoreticalaspects of anion···π interactions which is followed by a discussion of the existing X Preface experimentalevidenceforthistypeofinteraction.Both,solutionandcrystal- lographicstudiesareanalysed showingthepotentialimpactthatthistypeof interactioncouldhaveinthedesignofnewanionreceptors. The use of anions as templating agents is discussed by Vilar. The chapter startswithageneraloverviewoftheareaandadiscussionoftheapplications of anion templates in organic and coordination chemistry. The second part of the chapter deals with examples where anions are employed as templates in dynamic combinatorial libraries. This approach promises to provide an efficient routeforthesynthesis ofbetter andmoreselective anionreceptors. The last chapter by Ewen and Steinke also deals with the use of anions as templatesbutinthiscaseinthecontextofmolecularimprintedpolymers.The firsthalf ofthechapterprovidesan introductioninto molecularly imprinted polymers and this is followed by a detailed discussion of examples where anionicspecieshavebeenusedtoimprintthisclassofpolymericmaterials. The topics discussed in this volume provide an exciting and stimulating overviewofthemostrecentstudieswithinanionrecognitionandtemplation. Althoughthesupramolecularchemistryofanionstookalongtimetodevelop, itisnowamatureareathatprovidessolutionstochallengingproblems.Thereis nodoubtthatitsgrowthwillcontinueyieldingmoresophisticatedandefficient receptorsfortherecognitionofawiderangeofnegativelychargedspecies. London,February2008 RamónVilar Contents AnIntroductiontoAnionReceptorsBasedonOrganicFrameworks G.W.Bates·P.A.Gale . . . . . . . . . . . . . . . . . . . . . . . . . . . 1 Metal-BasedAnionReceptorSystems S.R.Bayly·P.D.Beer . . . . . . . . . . . . . . . . . . . . . . . . . . . . 45 RecentProgressofPhosphateDerivativesRecognition UtilizingArtificialSmallMolecularReceptorsinAqueousMedia S.Tamaru·I.Hamachi . . . . . . . . . . . . . . . . . . . . . . . . . . . 95 Anionsandπ-AromaticSystems.DoTheyInteractAttractively? P.Ballester . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 127 AnionTemplatesinSynthesisandDynamicCombinatorialLibraries R.Vilar . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 175 MolecularlyImprintedPolymersUsingAnionsasTemplates S.L.Ewen·J.H.G.Steinke . . . . . . . . . . . . . . . . . . . . . . . . . 207 SubjectIndex . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 249 StructBond(2008)129:1–44 DOI10.1007/430_2007_069 © Springer-VerlagBerlinHeidelberg Publishedonline:10November2007 AnIntroductiontoAnionReceptors BasedonOrganicFrameworks GarethW.Bates·PhilipA.Gale((cid:1)) SchoolofChemistry,UniversityofSouthampton,SouthamptonSO171BJ,UK [email protected] 1 Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1 2 NeutralReceptors . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2 2.1 AcyclicAmideandSulfonamide-BasedReceptors . . . . . . . . . . . . . . 2 2.2 MacrocyclicAmideReceptors . . . . . . . . . . . . . . . . . . . . . . . . . 6 2.3 UreaandThiourea-BasedReceptors . . . . . . . . . . . . . . . . . . . . . . 12 3 AromaticNHDonorContainingNeutralReceptors . . . . . . . . . . . . . 21 3.1 Pyrrole-BasedReceptors . . . . . . . . . . . . . . . . . . . . . . . . . . . . 21 3.2 CarbazoleandIndole-BasedReceptors . . . . . . . . . . . . . . . . . . . . 29 4 Hydroxy(OH)DonorsinNeutralReceptors . . . . . . . . . . . . . . . . . 32 5 ChargedReceptors . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 33 5.1 ImidazoliumandPyridinium-BasedReceptors . . . . . . . . . . . . . . . . 34 5.2 Guanidinium-BasedReceptors . . . . . . . . . . . . . . . . . . . . . . . . . 37 5.3 Ammonium-ContainingReceptors . . . . . . . . . . . . . . . . . . . . . . . 39 6 Conclusions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 42 References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 42 Abstract Thisreviewarticleprovidesabroadoverviewtotheareaofanioncoordination bysyntheticorganicreceptorsandincludesexamplesofdifferentfunctionalgroupsused to bind anions. The first section examines neutral anion receptors containing amide-, sulfonamide-, urea- and thiourea-based receptors. Then aromaticssuch as pyrrole, car- bazoleandindolearediscussedbeforeconcludingthediscussionofneutralsystemswith examplesofhydroxyOHdonors.Abriefoverviewofchargedsystemsisalsoprovided. Keywords Anionrecognition·Complexation·Crystalstructures·Hydrogenbonding· Supramolecularchemistry 1 Introduction The development ofnewanion receptors based onorganic frameworkscon- tinuestoattractconsiderableresearcheffort[1–4].Awidevarietyofsystems have been published in the last 15 years with both macrocyclic and acyclic
The list of books you might like
