318 Topics in Current Chemistry Editorial Board: K.N. Houk C.A. Hunter M.J. Krische J.-M. Lehn l l l S.V. Ley M. Olivucci J. Thiem M. Venturi P. Vogel l l l l C.-H. Wong H. Wong H. Yamamoto l l Topics in Current Chemistry Recently Published and Forthcoming Volumes LiquidCrystals:MaterialsDesignand AlkaloidSynthesis Self-Assembly VolumeEditor:Hans-JoachimKno¨lker VolumeEditor:CarstenTschierske Vol.309,2012 Vol.318,2012 FluorousChemistry Fragment-BasedDrugDiscoveryandX-Ray VolumeEditor:Istva´nT.Horva´th Crystallography Vol.308,2012 VolumeEditors:ThomasG.Davies, MultiscaleMolecularMethodsinApplied MarkoHyvo¨nen Chemistry Vol.317,2012 VolumeEditors:BarbaraKirchner,JadranVrabec Vol.307,2012 NovelSamplingApproachesinHigher DimensionalNMR SolidStateNMR VolumeEditors:MartinBilleter, VolumeEditor:JerryC.C.Chan VladislavOrekhov Vol.306,2012 Vol.316,2012 PrionProteins AdvancedX-RayCrystallography VolumeEditor:Jo¨rgTatzelt VolumeEditor:KariRissanen Vol.305,2011 Vol.315,2012 Microfluidics:TechnologiesandApplications Pyrethroids:FromChrysanthemumtoModern VolumeEditor:BingchengLin IndustrialInsecticide Vol.304,2011 VolumeEditors:NoritadaMatsuo,TatsuyaMori Vol.314,2012 Photocatalysis VolumeEditor:CarloAlbertoBignozzi UnimolecularandSupramolecular Vol.303,2011 ElectronicsII VolumeEditor:RobertM.Metzger ComputationalMechanismsofAuandPt Vol.313,2012 CatalyzedReactions VolumeEditors:ElenaSoriano, UnimolecularandSupramolecular Jose´Marco-Contelles ElectronicsI Vol.302,2011 VolumeEditor:RobertM.Metzger Vol.312,2012 ReactivityTuninginOligosaccharideAssembly VolumeEditors:BertFraser-Reid, Bismuth-MediatedOrganicReactions J.Cristo´balLo´pez VolumeEditor:ThierryOllevier Vol.301,2011 Vol.311,2012 LuminescenceAppliedinSensorScience Peptide-BasedMaterials VolumeEditors:LucaProdi,MarcoMontalti, VolumeEditor:TimothyDeming NelsiZaccheroni Vol.310,2012 Vol.300,2011 Liquid Crystals Materials Design and Self-Assembly Volume Editor: Carsten Tschierske With Contributions by T. 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Zanchetta Editor Prof.CarstenTschierske InstituteofChemistry OrganicChemistry MartinLutherUniversityHalle-Wittenberg Kurt-MothesStr.2 06120Halle/Saale Germany [email protected] ISSN0340-1022 e-ISSN1436-5049 ISBN978-3-642-27590-6 e-ISBN978-3-642-27591-3 DOI10.1007/978-3-642-27591-3 SpringerHeidelbergDordrechtLondonNewYork LibraryofCongressControlNumber:2011945782 #Springer-VerlagBerlinHeidelberg2012 Thisworkissubjecttocopyright.Allrightsarereserved,whetherthewholeorpartofthematerialis concerned,specificallytherightsoftranslation,reprinting,reuseofillustrations,recitation,broadcasting, reproductiononmicrofilmorinanyotherway,andstorageindatabanks.Duplicationofthispublication orpartsthereofispermittedonlyundertheprovisionsoftheGermanCopyrightLawofSeptember9, 1965,initscurrentversion,andpermissionforusemustalwaysbeobtainedfromSpringer.Violations areliabletoprosecutionundertheGermanCopyrightLaw. 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Printedonacid-freepaper SpringerispartofSpringerScience+BusinessMedia(www.springer.com) Volume Editor Prof.CarstenTschierske InstituteofChemistry OrganicChemistry MartinLutherUniversityHalle-Wittenberg Kurt-MothesStr.2 06120Halle/Saale Germany [email protected] Editorial Board Prof.Dr.KendallN.Houk Prof.Dr.StevenV.Ley UniversityofCalifornia UniversityChemicalLaboratory DepartmentofChemistryandBiochemistry LensfieldRoad 405HilgardAvenue CambridgeCB21EW LosAngeles,CA90024-1589,USA GreatBritain [email protected] [email protected] Prof.Dr.ChristopherA.Hunter Prof.Dr.MassimoOlivucci DepartmentofChemistry Universita`diSiena UniversityofSheffield DipartimentodiChimica SheffieldS37HF,UnitedKingdom ViaADeGasperi2 c.hunter@sheffield.ac.uk 53100Siena,Italy [email protected] Prof.MichaelJ.Krische Prof.Dr.JoachimThiem UniversityofTexasatAustin Institutfu¨rOrganischeChemie Chemistry&Biochemistry Department Universita¨tHamburg 1UniversityStationA5300 Martin-Luther-King-Platz6 AustinTX,78712-0165,USA 20146Hamburg,Germany [email protected] [email protected] Prof.Dr.Jean-MarieLehn Prof.Dr.MargheritaVenturi ISIS DipartimentodiChimica 8,alle´eGaspardMonge Universita`diBologna BP70028 viaSelmi2 67083StrasbourgCedex,France 40126Bologna,Italy [email protected] [email protected] vi EditorialBoard Prof.Dr.PierreVogel Prof.Dr.HenryWong LaboratoryofGlycochemistry TheChineseUniversityofHongKong andAsymmetricSynthesis UniversityScienceCentre EPFL–Ecolepolytechniquefe´derale DepartmentofChemistry deLausanne Shatin,NewTerritories EPFLSBISICLGSA [email protected] BCH5307(Bat.BCH) 1015Lausanne,Switzerland Prof.Dr.HisashiYamamoto pierre.vogel@epfl.ch ArthurHollyComptonDistinguished Prof.Dr.Chi-HueyWong Professor DepartmentofChemistry Professor of Chemistry, Scripps Research TheUniversityofChicago Institute 5735SouthEllisAvenue PresidentofAcademiaSinica Chicago,IL60637 AcademiaSinica 773-702-5059 128AcademiaRoad USA Section2,Nankang [email protected] Taipei115 Taiwan [email protected] Topics in Current Chemistry Also Available Electronically Topics in Current Chemistry is included in Springer’s eBook package Chemistry andMaterialsScience.Ifalibrarydoesnotoptforthewholepackagethebookseries may be bought on a subscription basis. 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Theobjectiveofeachthematicvolumeistogivethenon-specialistreader,whether at the university or in industry, a comprehensive overview of an area where new insightsofinteresttoalargerscientificaudienceareemerging. vii viii TopicsinCurrentChemistryAlsoAvailableElectronically Thus each review within the volume critically surveys one aspect of that topic and places it within the context of the volume as a whole. The most significant developmentsofthelast5–10yearsarepresented,usingselectedexamplestoillus- trate the principles discussed. A description of the laboratory procedures involved is often useful to the reader. The coverage is not exhaustive in data, but rather conceptual, concentrating on the methodological thinking that will allow the non- specialistreadertounderstandtheinformationpresented. Discussionofpossiblefutureresearchdirectionsintheareaiswelcome. Reviewarticlesfortheindividualvolumesareinvitedbythevolumeeditors. InreferencesTopicsinCurrentChemistryisabbreviatedTop CurrChemandis citedasajournal. ImpactFactor2010:2.067;Section“Chemistry,Multidisciplinary”:Rank44of144 Preface Sincetheirdiscoveryin1888,liquidcrystals(LCs)havedevelopedfromascientific curiositytoaninterdisciplinaryresearchfieldwithbroadcommercialapplications. LC displays (LCD) represent the most obvious and successful example for the practical application of LC, well know to a broad community. The light, flat and low power-consuming LCD is one of the key components of present mobile communicationanddataprocessingdevices,whichhavechangedourlivesconsid- erably.Nowadays,eventheTV-marketisdominatedbyLCDwhichallowsincred- ible screens sizes and resolutions. However, beside the well known display technologytherearemanyotherapplicationsofliquidcrystals,forexamplepolar- izedlightreflectingandphotonicbandgapmaterialsandlightmodulators.Liquid crystallinepolymersare presentlyusedfor highstrengthfibres,fortheencapsula- tion of microelectronic circuits and the construction of micro-electromechanical andmicro-fluidicdevices.NumerousnewapplicationsofLCarealsoapproaching, such as organic light emitting diodes, photovoltaic devices, organic field effect transistors,tuneablelasersandmanyothers.Besidesthenumeroustechnicalappli- cations there are also an increasing number of biomedical applications for drug delivery, gene delivery, sensors and as promising materials for artificial bones, tissues and actuators. In a more general sense, the combination of order and mobilityintheLC state provides uniqueproperties andisabasicrequirementfor self-assemblyandstructureformationintechnicalandbio-systems. However,theLCdisplaysarestillbasedonthesimplestmodeofLCorganiza- tion, the nematic phase, which comprises only an orientational order of the mole- cules, new applications, as for example in organic electronics also require the directeddesignofpositionalorderinone,twoorthreedimensionsasprovidedby smectic, columnar and cubic phases, respectively. In this way, through molecular design and synthesis of new LC molecules, the complexity of LC phases can be increasedandthisisthebasisfortheemergenceofnewmaterialsproperties,paving thewaytonewfutureapplications.Onerecentexampleisprovidedbytheso-called bent-core molecules, where ferroelectricity and spontaneous achiral symmetry breakingemergeinwellordered,butstillfluidsystems. ix x Preface A number of fundamental aspects of liquid crystals chemistry were presented in volumes 94 and 95 of Structure and Bonding, edited by D. M. P. Mingos and published in 1999 and also in volume 128 of the same series, edited by T. Kato and published in 2008. Another monograph was published by Springer in 2007 (Thermotropic Liquid Crystals, edited by A. Ramamoorthy) and deals more with physical aspects of LC self assembly and methods of their investigation. This volume intends to shed light on a selection of different aspects of contemporary liquid crystal chemistry, focussing on molecular design carried out in order to influencetheself-assemblybehaviourofLC-formingmoleculesinaspecificway. The editor has intended to avoid duplications with subjects occurring in the previousvolumesoftheseriesStructureandBondingandtoprovidethereaderwith mostupdateinformationondesignandself-assemblyofLCmaterials.Thisvolume in the Topics in Current Chemistry series combines eight chapters from different areas,startingwithreviewsonthecurrentstateinthefieldsofLCswithperfluori- natedsegmentsandLCsbasedoncrownetherstructures.Thefirstoneisfocussed onnano-segregationasabasictoolforLC-design,leadingtospecificpropertiesand new modes of self-assembly in liquid crystals. The second one provides a link to host-guest chemistry, a major area of supramolecular chemistry. The first chapter alsogivesashortintroductionintothefieldofLCself-assemblyandoffersabrief description of the most important fundamental LC phase structures. LC phases formedbyunusualmolecules,namelythree-arm-starmoleculesarereviewedinthe third chapter. This is followed by a chapter presenting an overview of soft DNA- based structures, not only covering LC phases but also including other soft struc- tures based on DNA nanotechnology, which provides some examples for the importanceofLCselfassemblyinbio-systemsandfortheoriginoflife.Asalready mentioned above, another contemporary field of research is related to so-called bent-core mesogens. Two chapters are devoted to this subject, one reviewing complexphaseswithtwo-dimensionalorderandtheotheronefocussingonspon- taneous achiral symmetry breaking in bent-core LC and also in other LC phases. Another current research field deals with the combination of nano-particles and LCs.Nano-particlescaneitherbecombinedwithunitspromotingtheirmesogenity andenablingthemtoorganizeintowelldefinedperiodicLCstructures,ortheself assemblyof nano-particlescan be mediated by aLC host matrix. Finally, there is alsoaninfluenceofthenano-particlesonthephasestructureoftheLChost.Thelast chapterisdevotedtothedirectedmoleculardesignofphoto-luminescentLC. It is obvious that this volume cannot be fully comprehensive, but at least it should provide a rough overview, covering some of the important subjects in the field of liquid crystal design and self-assembly. Nevertheless, I hope the present volumewillbehighlyinformativeandinspiringforchemistsandphysicistswhoare interested in developing new materials based on the unique combination of order andmobilityprovidedbytheLCstate. Halle,December2011 CarstenTschierske