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Core Concepts in Supramolecular Chemistry and Nanochemistry Jonathan W. Steed, Durham University, UK David R. Turner, Monash University, Australia Karl J. Wallace, University of Southern Mississippi, USA Core Concepts in Supramolecular Chemistry and Nanochemistry Core Concepts in Supramolecular Chemistry and Nanochemistry Jonathan W. Steed, Durham University, UK David R. Turner, Monash University, Australia Karl J. Wallace, University of Southern Mississippi, USA Copyright©2007 JohnWiley&Sons,Ltd,TheAtrium,SouthernGate,Chichester, WestSussex,PO198SQ,England Telephone (cid:2)+44(cid:3)1243779777 Email(forordersandcustomerserviceenquiries):[email protected] VisitourHomePageonwww.wiley.com AllRightsReserved.Nopartofthispublicationmaybereproduced,storedinaretrievalsystemor transmittedinanyformorbyanymeans,electronic,mechanical,photocopying,recording,scanningor otherwise,exceptunderthetermsoftheCopyright,DesignsandPatentsAct1988orunderthetermsofa licenceissuedbytheCopyrightLicensingAgencyLtd,90TottenhamCourtRoad,LondonW1T4LP,UK, withoutthepermissioninwritingofthePublisher.RequeststothePublishershouldbeaddressedtothe PermissionsDepartment,JohnWiley&Sons,Ltd,TheAtrium,SouthernGate,Chichester,WestSussex PO198SQ,England,[email protected],orfaxedto(+44)1243770620. Designationsusedbycompaniestodistinguishtheirproductsareoftenclaimedastrademarks.Allbrand namesandproductnamesusedinthisbookaretradenames,servicemarks,trademarksorregistered trademarksoftheirrespectiveowners.ThePublisherisnotassociatedwithanyproductorvendor mentionedinthisbook. Thispublicationisdesignedtoprovideaccurateandauthoritativeinformationinregardtothesubject mattercovered.ItissoldontheunderstandingthatthePublisherisnotengagedinrenderingprofessional services.Ifprofessionaladviceorotherexpertassistanceisrequired,theservicesofacompetent professionalshouldbesought. OtherWileyEditorialOfﬁces JohnWiley&Sons,Inc.,111RiverStreet,Hoboken,NJ07030,USA Jossey-Bass,989MarketStreet,SanFrancisco,CA94103-1741,USA Wiley-VCHVerlagGmbH,Boschstr.12,D-69469Weinheim,Germany JohnWiley&Sons,AustraliaLtd,33ParkRoad,Milton,Queensland4064,Australia JohnWiley&Sons,(Asia)PteLtd,2ClementiLoop#02-01,JinXingDistripark,Singapore129809 JohnWiley&Sons,CanadaLtd,6045FreemontBlvd,Mississauga,Ontario,L5R4J3 Wileyalsopublishesitsbooksinavarietyofelectronicformats.Somecontentthatappearsinprintmay notbeavailableinelectronicbooks. AnniversaryLogoDesign:RichardJ.Paciﬁco LibraryofCongressCataloginginPublicationData Steed,JonathanW.,1969– Coreconceptsinsupramolecularchemistryandnanochemistry/JonathanW.Steed, DavidR.Turner,KarlJ.Wallace. p. cm. Includesbibliographicalreferencesandindex. ISBN978-0-470-85866-0(cloth:alk.paper)—ISBN978-0-470-85867-7(pbk.:alk.paper) 1. Supramolecularchemistry. 2. Nanochemistry. I.Turner,DavidR. II. Wallace,KarlJ. III.Title. QD878.S732007 547′.7—dc22 2007001274 BritishLibraryCataloguinginPublicationData AcataloguerecordforthisbookisavailablefromtheBritishLibrary ISBN-13:978-0-470-85866-0(HB) ISBN-13:978-0-470-85867-7(PB) ThefrontcoverdepictstheMinoanPhaestosdisc,ca.1600BC.Thisdiscbearshieroglyphiccharacters, separatelyimpressedbymeansofpunchesandarrangedinaspiral.Likemanyaspectsofthemolecular world,thecharactershaveyettobedeciphered.PhotocourtesyofIainForbes,DepartmentofArchaelogy, CambridgeUniversity,UK. Typesetin10/12ptPalatinobyIntegraSoftwareServicesPvt.Ltd,Pondicherry,India PrintedandboundinGreatBritainbyAntonyRoweLtd.,Chippenham,Wiltshire Thisbookisprintedonacid-freepaperresponsiblymanufacturedfromsustainableforestryinwhichat leasttwotreesareplantedforeachoneusedforpaperproduction. To Ben and Joshua Contents Preface ix About the authors xi 1 Introduction 1 1.1 Whatissupramolecularchemistry? 1 1.2 Selectivity 4 1.3 Supramolecularinteractions 17 1.4 Supramoleculardesign 26 References 27 Suggestedfurtherreading 27 2 Solution host–guest chemistry 29 2.1 Introduction:guestsinsolution 29 2.2 Macrocyclicversusacyclichosts 30 2.3 Cationbinding 36 2.4 Anionbinding 52 2.5 Metal-containingreceptors 66 2.6 Simultaneouscationandanionreceptors 73 2.7 Neutral-moleculebinding 82 2.8 Supramolecularcatalysisandenzymemimics 97 References 104 3 Self-assembly 107 3.1 Introduction 107 3.2 Biologicalself-assembly 114 3.3 Ladders,polygonsandhelices 121 3.4 Rotaxanes,catenanesandknots 133 3.5 Self-assemblingcapsules 156 References 167 4 Solid state supramolecular chemistry 171 4.1 Introduction 171 4.2 Zeolites 172 4.3 Clathrates 179 4.4 Clathratehydrates 187 viii contents 4.5 Crystalengineering 194 4.6 Coordinationpolymers 209 References 225 5 Nanochemistry 229 5.1 Introduction 229 5.2 Nanomanipulation 233 5.3 Moleculardevices 237 5.4 Self-assembledmonolayers(SAMs) 254 5.5 Softlithography 264 5.6 Nanoparticles 266 5.7 Fullerenesandnanotubes 272 5.8 Dendrimers 277 5.9 Fibres,gelsandpolymers 279 5.10 Nanobiologyandbiomimeticchemistry 284 References 293 Index 297

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Supramolecular chemistry and nanochemistry are two strongly interrelated cutting edge frontiers in research in the chemical sciences. The results of recent work in the area are now an increasing part of modern degree courses and hugely important to researchers. Core Concepts in Supramolecular Chemis