Supramolecular Polymer Networks and Gels PDF
Preview Supramolecular Polymer Networks and Gels
Advances in Polymer Science 268 Sebastian Seiffert Editor Supramolecular Polymer Networks and Gels 268 Advances in Polymer Science EditorialBoard: A.Abe,Yokohama,Japan A.-C.Albertsson,Stockholm,Sweden G.W.Coates,Ithaca,NY,USA J.Genzer,Raleigh,NC,USA S.Kobayashi,Kyoto,Japan K.-S.Lee,Daejeon,SouthKorea L.Leibler,Paris,France T.E.Long,Blacksburg,VA,USA M.Mo¨ller,Aachen,Germany O.Okay,Istanbul,Turkey V.Percec,Philadelphia,PA,USA B.Z.Tang,HongKong,China E.M.Terentjev,Cambridge,UK M.J.Vicent,Valencia,Spain B.Voit,Dresden,Germany U.Wiesner,Ithaca,NY,USA X.Zhang,Beijing,China Aims and Scope TheseriesAdvancesinPolymerSciencepresentscriticalreviewsofthepresentand futuretrendsinpolymerandbiopolymerscience.Itcoversallareasofresearchin polymerandbiopolymerscienceincludingchemistry,physicalchemistry,physics, materialscience. The thematic volumes are addressed to scientists, whether at universities or in industry,whowishtokeepabreastoftheimportantadvancesinthecoveredtopics. AdvancesinPolymerScienceenjoysalongstandingtraditionandgoodreputa- tioninitscommunity.Eachvolumeisdedicatedtoacurrenttopic,andeachreview critically surveys one aspect of that topic, to place it within the context of the volume.Thevolumestypicallysummarizethesignificantdevelopmentsofthelast 5to10yearsanddiscussthemcritically,presentingselectedexamples,explaining and illustrating the important principles, and bringing together many important referencesofprimaryliterature.Onthatbasis,futureresearchdirectionsinthearea canbediscussed.AdvancesinPolymerSciencevolumesthusareimportantrefer- ences for every polymer scientist, as well as for other scientists interested in polymerscience-asanintroductiontoaneighboringfield,orasacompilationof detailedinformationforthespecialist. Review articles for the individual volumes are invited by the volume editors. Singlecontributionscanbespeciallycommissioned. Readership:Polymerscientists,orscientistsinrelatedfieldsinterestedinpoly- merandbiopolymerscience,atuniversitiesorinindustry,graduatestudents. Specialoffer: For all clients with a standing order we offer the electronic form of Advances in PolymerSciencefreeofcharge. Moreinformationaboutthisseriesat http://www.springer.com/series/12 Sebastian Seiffert Editor Supramolecular Polymer Networks and Gels With contributions by (cid:1) (cid:1) (cid:1) M. Anthamatten M. Chau P.Y.W. Dankers (cid:1) (cid:1) (cid:1) (cid:1) B.W. Greenland W. Hayes E. Kumacheva P. Li (cid:1) (cid:1) (cid:1) (cid:1) (cid:1) R. Liu O. Okay A.C.H. Pape T. Rossow S. Seiffert S.E. Sriskandha (cid:1) H. The´rien-Aubin Editor SebastianSeiffert FreieUniversita¨tBerlin InstituteofChemistryandBiochemistry Berlin Germany ISSN0065-3195 ISSN1436-5030 (electronic) AdvancesinPolymerScience ISBN978-3-319-15403-9 ISBN978-3-319-15404-6 (eBook) DOI10.1007/978-3-319-15404-6 LibraryofCongressControlNumber:2015936665 SpringerChamHeidelbergNewYorkDordrechtLondon ©SpringerInternationalPublishingSwitzerland2015 Thisworkissubjecttocopyright.AllrightsarereservedbythePublisher,whetherthewholeorpartof the material is concerned, specifically the rights of translation, reprinting, reuse of illustrations, recitation, broadcasting, reproduction on microfilms or in any other physical way, and transmission or information storage and retrieval, electronic adaptation, computer software, or by similar or dissimilarmethodologynowknownorhereafterdeveloped. The use of general descriptive names, registered names, trademarks, service marks, etc. in this publicationdoesnotimply,evenintheabsenceofaspecificstatement,thatsuchnamesareexempt fromtherelevantprotectivelawsandregulationsandthereforefreeforgeneraluse. Thepublisher,theauthorsandtheeditorsaresafetoassumethattheadviceandinformationinthis book are believed to be true and accurate at the date of publication. Neither the publisher nor the authors or the editors give a warranty, express or implied, with respect to the material contained hereinorforanyerrorsoromissionsthatmayhavebeenmade. Printedonacid-freepaper Springer International Publishing AG Switzerland is part of Springer Science+Business Media (www.springer.com) Preface Supramolecular polymer networks and gels consist of monomeric, oligomeric, or polymeric building blocks transiently and dynamically interconnected by non- covalent bonds. This mode of interconnection is responsible for the promising potential of these materials to serve as adaptive, self-healing, and stimuli-respon- sivecoatings,elastomers,andscaffoldsinboththelifeandmaterialssciences.To make this truly useful, it is necessary to achieve systematic and comprehensive understandingofthemolecular-scaleinteractionsandmacromolecular-scalestruc- tures anddynamics ofthese networksandgels. Various efforts have been and are beingmadetoachievesuchunderstandingandtodevelopadvancedfunctionalsoft materials.Itisthereforeagoodtimetoreviewsomeoftheseactivities;thisvolume aims to provide such a review. In the following chapters, several examples and achievements of recent and current research activities are given. Anthamatten reviews hydrogen-bonding interactions to form soft solid polymer-network struc- turesandmaterials,includingglasses,melts,andelastomers.Okayaddsaperspec- tive on the design, mechanics, and self-healing of hydrogels formed via hydrophobic interactions, with a particular emphasis on the role of surfactant micelles within the gels. The development of donor–acceptor – stacking interac- tions that serve as transient crosslinks in self-healable supramolecular polymer networks is discussed by Greenland and Hayes. Chau, Sriskandha, The´rien- Aubin, and Kumacheva highlight recent progress in the field of nanofibrillar supramolecular gels, discussing both synthetic and natural materials. Liu adds a particular view on the potential of cellulose and cellulose derivatives for the formation of chemical and physical gels and microgels, with a specific focus on supramolecular interactions within them. Finally, Pape and Dankers provide a reviewonsupramolecularhydrogelsofseveralkindsforuseinthefieldofregener- ativemedicine. Iwouldliketotakethechancetogreatlythankallthesecolleaguesforproviding thesedeepandillustrativeinsightsintotheirworkandthatoftheirpeers.Ibelieve v vi Preface thatthecollectionofcontributionspresentedinthisvolumetrulyarcsfromfunda- mentalphysical-chemicalinvestigationtoadvanceddevelopmentanduseofsupra- molecular polymer networks and gels, which I expect to further evolve as a particularlypromisingandfascinatingclassofsoftmatterinthenearfuture. Berlin SebastianSeiffert April2015 Contents SupramolecularPolymerNetworks:Preparation,Properties, andPotential .................................................................... 1 TorstenRossowandSebastianSeiffert HydrogenBondinginSupramolecularPolymerNetworks:Glasses, Melts,andElastomers ........................................................ 47 MitchellAnthamatten Self-HealingHydrogelsFormedviaHydrophobicInteractions .......... 101 OguzOkay Donor–Acceptorp–pStackingInteractions:FromSmallMolecule ComplexestoHealableSupramolecularPolymerNetworks ............. 143 WayneHayesandBarnabyW.Greenland SupramolecularNanofibrillarPolymerHydrogels ........................ 167 MokitChau,ShivanthiEaswariSriskandha,He´lo¨ıseThe´rien-Aubin, andEugeniaKumacheva CelluloseGelsandMicrogels:Synthesis,Service,andSupramolecular Interactions ................................................................... 209 PingpingLiandRuigangLiu SupramolecularHydrogelsforRegenerativeMedicine ................... 253 A.C.H.PapeandPatriciaY.W.Dankers Index .......................................................................... 281 vii Supramolecular Polymer Networks: Preparation, Properties, and Potential TorstenRossowandSebastianSeiffert Contents 1 SupramolecularInteractions................................................................. 2 2 SupramolecularPolymerNetworksandOrganogels........................................ 5 2.1 HydrogenBonding..................................................................... 5 2.2 MetalComplexation.................................................................... 12 2.3 DynamicsinSupramolecularPolymerNetworks..................................... 18 3 SupramolecularHydrogels................................................................... 20 3.1 HydrogenBonding..................................................................... 21 3.2 MetalComplexation.................................................................... 24 3.3 MacrocyclicInclusionComplexation................................................. 26 3.4 IonicInteractions....................................................................... 30 3.5 HydrophobicInteractions.............................................................. 32 4 Applications.................................................................................. 33 4.1 Self-Healing............................................................................ 33 4.2 ShapeMemory......................................................................... 34 4.3 DrugDelivery.......................................................................... 35 4.4 MicrogelsforCellEncapsulation...................................................... 36 5 ConclusionsandOutlook.................................................................... 38 References........................................................................................ 38 Abstract Supramolecular polymer networks consist of macromolecules interconnected by transient, noncovalent bonds such as those through hydrogen bonding, transition metal complexation, hydrophobic interaction, ionic attraction, or π–π stacking. These networks form an extraordinarily useful class of soft, stimuli-sensitive materials. Although they assemble to strong materials under T.Rossow InstituteofChemistryandBiochemistry,FreieUniversita¨tBerlin,Takustr.3,14195Berlin, Germany S.Seiffert(*) InstituteofChemistryandBiochemistry,FreieUniversita¨tBerlin,Takustr.3,14195Berlin, Germany SoftMatterandFunctionalMaterials,Helmholtz-ZentrumBerlin,Hahn-Meitner-Platz1, 14109Berlin,Germany e-mail:[email protected] ©SpringerInternationalPublishingSwitzerland2015 1 S.Seiffert(ed.),SupramolecularPolymerNetworksandGels,AdvancesinPolymer Science268,DOI10.1007/978-3-319-15404-6_1 2 T.RossowandS.Seiffert favorable conditions, they are easily disassembled under other conditions. This ambivalentnaturerenderssupramolecularpolymernetworksusefulforapplications in drug delivery, tissue engineering, self-healing, and shape-memory materials. Theseapplicationsrequireadeepandcomprehensiveunderstandingofthephysical chemistry of supramolecular networks, with a particular view to the complex interplay between their structure, dynamics, and properties. Approaches that have attemptedtoderivesuchknowledgeareoftenbasedoninvestigationsofsupramo- lecular polymer networks in the melt or of supramolecular polymer networks swollen in organic media. These approaches are reviewed in the first part of this chapter. In the second part, we focus on the preparation and characterization of supramolecularhydrogelsbasedonsyntheticandnaturalprecursorsandrevealtheir utilityandpotentialinlifescienceapplications. Keywords Supramolecular polymer gels (cid:129) Stimuli-responsive materials (cid:129) Noncovalentinteractions(cid:129)Supramolecularnetworkdynamics(cid:129)Self-assembly 1 Supramolecular Interactions “Supramolecular chemistry may be defined as ‘chemistry beyond the molecule’, bearingontheorganizedentitiesofhighercomplexitythatresultfromtheassoci- ationoftwoormorechemicalspeciesheldtogetherbyintermolecularforces.”This definitionwasgivenbyLehnin1987[1]whenhereceivedtheNobelprizetogether with C. J. Pedersen and D. J. Cram for their work on host–guestchemistry. Since then,supramolecularchemistryhasgainedincreasingattentionanddevelopedinto an important, broad, and active field of research [2–4]. Today, research on supra- molecular chemistry can be subdivided into several categories: host–guest com- plexes[5–7],self-assembledarchitectures[8,9],supramolecularpolymers[10–14], supramoleculargels[15–18],andsupramolecularpolymernetworks[19,20]. The term “supramolecular polymer” refers to a polymer built of monomeric units associated through directional noncovalent physical interactions. Supramo- leculargelstypicallyconsistoflowmolecularweightprecursorsthatself-assemble intothree-dimensionalnetworksthroughnoncovalentinteractions;thesematerials are often brittle and hard to customize. In contrast, supramolecular polymer net- worksconsistofcovalentlyjoinedmacromolecularbuildingblocks(polymers)that are functionalized with motifs that can bind to each other through noncovalent interactionssuchashydrogenbonding[21–23],transitionmetalcomplexation[11, 24,25],hydrophobicinteraction[26],ionicattraction[10],orπ–πstacking[27–29], serving to assemble the polymer chains into a network. Noncovalent interactions strongly vary in their strength, as shown in Fig. 1. As a result, supramolecular polymer materials can be tuned to exhibit different mechanical properties by customuseoftheseinteractionsforpolymercross-linking. Supramolecularpolymernetworkscombinethecharacteristicsofchemicaland physical networksand can betailored tospecific needs throughthe use ofmacro- molecular building blocks. Although they form strong materials under favorable
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