Progress in controlled radical polymerization : mechanisms and techniques PDF
Preview Progress in controlled radical polymerization : mechanisms and techniques
g or s. c Progress in Controlled a s.1 b0 u0 pw p://0.f Radical Polymerization: htt10 2 | 2-1 0101 Mechanisms and Techniques 22 pril 8, 21/bk- A0 EY on oi: 10.1 Ld KE2 | R01 E2 A B20, NIch ORMar LIFb): Ae CW V OF Date ( NIn d by Ublicatio eu dP oa nl w o D In Progress in Controlled Radical Polymerization: Mechanisms and Techniques; Matyjaszewski, K., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2012. g or s. c a s.1 b0 u0 pw p://0.f htt10 2 | 2-1 11 00 22 pril 8, 21/bk- A0 EY on oi: 10.1 Ld KE2 | R01 E2 A B20, NIch ORMar LIFb): Ae CW V OF Date ( NIn d by Ublicatio eu dP oa nl w o D In Progress in Controlled Radical Polymerization: Mechanisms and Techniques; Matyjaszewski, K., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2012. 1100 ACS SYMPOSIUM SERIES Progress in Controlled Radical Polymerization: Mechanisms and Techniques g or s. c a s.1 b0 puw0 Krzysztof Matyjaszewski, Editor p://0.f htt10 Carnegie Mellon University 2 | 2-1 Pittsburgh, Pennsylvania 11 00 22 pril 8, 21/bk- Brent S. Sumerlin, Editor A0 EY on oi: 10.1 SouthernDMaleltahso,dTiesxtaUsniversity Ld KE2 | R01 Nicolay V. Tsarevsky, Editor E2 A B20, Southern Methodist University NIch Dallas, Texas ORMar LIFb): Ae CW V OF Date ( NIn d by Ublicatio ACSDivisioSnpoofnPsoorlyedmberyCthheemistry, Inc. eu dP oa nl w o D AmericanChemicalSociety,Washington,DC DistributedinprintbyOxfordUniversityPress,Inc. In Progress in Controlled Radical Polymerization: Mechanisms and Techniques; Matyjaszewski, K., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2012. LibraryofCongressCataloging-in-PublicationData g or Progressincontrolledradicalpolymerization:mechanismsandtechniques/ cs. KrzysztofMatyjaszewski,BrentS.Sumerlin,NicolayV.Tsarevsky,editor[s];sponsored a bs.01 bytheACSDivisionofPolymerChemistry,Inc. u0 pw p.cm.-- (ACSsymposiumseries;1100) p://0.f Includesbibliographicalreferencesandindex. htt10 ISBN978-0-8412-2699-9 2 | 2-1 1. Additionpolymerization.2. Radicals(Chemistry) I.Matyjaszewski,K.(Krzysztof) 11 2020 II.Sumerlin,BrentS.III.Tsarevsky,NicolayV.IV.AmericanChemicalSociety. pril 8, 21/bk- DTivPi1si5o6n.Po6fPP7o6ly2m01e2rChemistry,Inc. A0 EY on oi: 10.1 541′.224--dc23 2012005349 Ld KE2 | R01 E2 A B20, NIch ThepaperusedinthispublicationmeetstheminimumrequirementsofAmericanNational ORMar Standard for Information Sciences—Permanence of Paper for Printed Library Materials, LIFb): ANSIZ39.48n1984. Ae CW V OF Date ( CDoisptyrirbiguhtetd©in2p0r1i2ntAbmyeOrixcfaonrdCUhenmiviecraslitSyoPcrieetsys,Inc. NIn d by Ublicatio oAfllthReiUgh.Sts.RCeospeyrrviegdh.tRAecptriosgarllaopwhiecdcfoopryinintegrnbaelyuosnedotnhlayt,pperromviidtteeddtbhyatSaepcteiro-ncsha1p0t7erofre1e0o8f eu oad P $40.25plus$0.75perpageispaidtotheCopyrightClearanceCenter,Inc.,222Rosewood nl Drive,Danvers,MA01923,USA.Republicationorreproductionforsaleofpagesinthis w o bookispermittedonlyunderlicensefromACS.Directtheseandotherpermissionrequests D toACSCopyrightOffice,PublicationsDivision,115516thStreet,N.W.,Washington,DC 20036. Thecitationoftradenamesand/ornamesofmanufacturersinthispublicationisnottobe construedasanendorsementorasapprovalbyACSofthecommercialproductsorservices referenced herein; nor should the mere reference herein to any drawing, specification, chemicalprocess, orotherdataberegardedasalicenseorasaconveyanceofanyright or permission to the holder, reader, or any other person or corporation, to manufacture, reproduce,use,orsellanypatentedinventionorcopyrightedworkthatmayinanywaybe relatedthereto. Registerednames,trademarks,etc.,usedinthispublication,evenwithout specificindicationthereof,arenottobeconsideredunprotectedbylaw. PRINTEDINTHEUNITEDSTATESOFAMERICA In Progress in Controlled Radical Polymerization: Mechanisms and Techniques; Matyjaszewski, K., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2012. Foreword The ACS Symposium Series was first published in 1974 to provide a mechanism for publishing symposia quickly in book form. The purpose of g the series is to publish timely, comprehensive books developed from the ACS or s. sponsoredsymposiabasedoncurrentscientificresearch. Occasionally,booksare c a s.1 developed from symposia sponsored by other organizations when the topic is of b0 puw0 keeninteresttothechemistryaudience. p://0.f 12 | htt12-110 forapBperfoopreriaatgereaenidncgotmoppruebhleisnhsiavebocookv,etrhaegeparonpdofsoerdintatebrleesottfoctohneteanutdsieisncreev.iSeowmede 00 pril 8, 221/bk-2 cpoampeprsremheanysibveeenxecsslu.deWdhtoenbeatpteprrofopcriuastet,heovbeorovki;ewothoerrsinmtraoydbuectaodrydecdhtaoptperrosviadree EY on Aoi: 10.10 aadnddemd.anDursacfrtsipotsfcahreapptreerpsaarreedpienecr-armeveireaw-reedadpyrifoorrmtoafit.nalacceptanceorrejection, Ld KE2 | As a rule, only original research papers and original review papers are ER201 included in the volumes. Verbatim reproductions of previous published papers A B20, arenotaccepted. NIch ORMar LIFb): Ae ACSBooksDepartment CW V OF Date ( NIn d by Ublicatio eu dP oa nl w o D In Progress in Controlled Radical Polymerization: Mechanisms and Techniques; Matyjaszewski, K., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2012. Editors' Biographies Krzysztof Matyjaszewski Krzysztof Matyjaszewski is the J.C. Warner University Professor of Natural Sciences and Director of the Center for Macromolecular Engineering at org CarnegieMellonUniversity. Hedevelopedatomtransferradicalpolymerization, cs. commercialized in the U.S., Europe, and Japan. He has co-authored 700 a 2 | http://pubs.2-1100.ot001 4Pfpr0uroibmzUleic.tSiahn.teioaCAnnhmdse(me1cr2iiitsc0etadrniync,Ctae2.hr0ne50am09t,ii0ocP0nar0laelSstiiopmdcaeeitneesttn,iyath:sl-.i2Gn0Mdr1ee1aextnHy1j1eCa4rshm)ze,eamcwnoinss-ketMridyirateeCrckdheAa1ivl4wleedbanorgdtohe,ke2sA,02w1a0n1a1rd1Adh,wWoaalondrlddsf 11 2020 inAppliedPolymerScience,2002PolymerChemistryAward,and1995Creative RKELEY on April 8, 012 | doi: 10.1021/bk- EPonlgyiBmnereeernriCtnSgh.,eSmPuoimslitserhyrliAAncwgaardareddm.uayBHteoredfeiwSnscittaiheSmna.ceBeSms.S,uba.menfrrdoeomRrflutiNhsnseoiraUtnhSACAacraNodlaeitnmioaynSaotlaftASeccUiaendnievcmeesrys.iotyf E2 A B20, (1998)andaPh.D.fromtheUniversityofSouthernMississippi(2003)underthe NIch directionofCharlesMcCormick. AfterservingasaVisitingAssistantProfessor Rar OM at Carnegie Mellon University under the direction of Krzysztof Matyjaszewski LIFb): (2003-2005), he joined the Department of Chemistry at Southern Methodist Ae CW University (Dallas, Texas, USA) as an assistant professor in 2005 and was V OF Date ( promoted to associate professor in 2009. In 2012, Prof. Sumerlin joined the d by UNIblication DrReeecspeeiavarrtemcdhesnFevteelolrofawlCaswhhieapmr.diss,triyncalutdtihnegaUNniSvFerCsiAtyRoEfERFloArwidaar.daPndroafn. ASlfurmedePrl.inSlohaans eu dP a o nl w Nicolay V. (Nick) Tsarevsky o D Nicolay V. (Nick) Tsarevsky obtained a M.S. in theoretical chemistry and chemical physics from the University of Sofia, Bulgaria (1999) and a Ph.D. in chemistry from Carnegie Mellon University (CMU, 2005, under Krzysztof Matyjaszewski). He was visiting assistant professor at the CMU Department of Chemistry (2005-2006), associate director of the CRP Consortium (2006-2007), and CSO of ATRP Solutions, Inc. (2007-2010). He joined the Department of Chemistry at Southern Methodist University in 2010. Research interests include polymerization techniques, functional materials, coordination chemistry, catalysis, and the chemistry of hypervalent compounds. He is the (co)author of over65peer-reviewedpapersorbookchapters,atextbook,andseveralpatents. ©2012AmericanChemicalSociety In Progress in Controlled Radical Polymerization: Mechanisms and Techniques; Matyjaszewski, K., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2012. Preface This book and a following volume are addressed to chemists who are interested in radical processes and especially in controlled/living radical g polymerization. Theysummarizethemostrecentaccomplishmentsinthefield. or s. Thetwovolumescomprisethetopicalreviewsandspecialists'contributions c a s.1 presented at the American Chemical Society Symposium entitled Controlled/ b0 2 | http://pu2-1100.pr0 L2A9iCviS-ngSSeyRpmtaedpmiocbsaiealr Ph1eo,lld2ym0i1ne1r.iSzaanTtihoFenraDtnhecanitsvcewor,aMsCaehleeitfliodnrgniinwa,aDsinean1vs9ee9rq,7u,CelionltooNratehdweo,pOrAreluvegiaounussst, 0101 Louisiana, in 1999, in Boston, Massachusetts, in 2002, in Washington, DC, 22 pril 8, 21/bk- Sinym20p0o5siuamndSeinriePshViolalduemlpeh6i8a,5:inCo2n0tr0o8l.ledTRhaedyicwalePreolsyummermizaartiizoend,VinoluthmeeA76C8S: A0 EY on oi: 10.1 VCoolnutmroelle8d5/4L:iviAndgvRanacdeicsailnPColoynmtreorlilzeadti/oLniv:inPgroRgardesicsailnPAoTlyRmP,erNizMatPioann,dVRolAuFmTe, RKEL012 | d 9V4o4lu:mCeo1n0t2ro3l:leCdo/LnitvroinllgedR/LadiviicnaglRPaodlyicmaelrPizoaltyimone:rizFartoiomn:SPynrothgeresissstionAMTaRtPer,iaanlsd, E2 A B20, Volume 1024: Controlled/Living Radical Polymerization: Progress in RAFT, NIch DT,NMPandOMRP.TheDenverMeetingwasverysuccessfulwith96lectures Rar and 83 posters presented. This illustrates a continuous growth in comparison to OM LIFb): theSanFranciscoMeeting(32lectures),theNewOrleansMeeting(50lectures), CAWe theBostonMeeting(80lectures),theWashingtonMeeting(77lectures),andthe V OF Date ( PhilaTdheelp4h1iachMapeteetrinsgsu(b9m0iltetecdtufroers)p.ublicationintheACSSymposiumseriescould NIn d by Ublicatio nvootlufimtienst.oWoneedveocliudmede,toanddivthideeretfhoerecwhaepwteersreinastokevdobluymAeCsSretloatsepdlittothmemechinatnoistwmos eu andtechniques(21chapters)andmaterials(20chapters). dP a nlo The first chapter in this volume provides an overview of the current status w of controlled/living radical polymerization (CRP) systems. The following three o D chaptersdiscussimportantissuesrelevanttoallradicalpolymerizationmethods. The mechanistic and kinetic topics of ATRP are covered in seven chapters, and the next two are related to commercial aspects of ATRP. Two chapters discuss organometallicradicalpolymerization,andthelastsixpresentrecentprogressin reversibleaddition-fragmentationchaintransferpolymerizationandinreversible iodinetransferpolymerization. The accompanying volume contains seven chapters on macromolecular architecture,twochaptersonmaterialsforelectronicapplications,eightonhybrid materialsandfouronbio-relatedmaterials. Forty-one chapters published in two volumes show that CRP has made significantprogresswithinthelast15years. Newsystemshavebeendiscovered; xi In Progress in Controlled Radical Polymerization: Mechanisms and Techniques; Matyjaszewski, K., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2012. substantial progress has been achieved in understanding the mechanism and kineticsofreactionsinvolvedinallCRPsystems. Significantprogresshasbeen made towards a comprehensive relationship between molecular structure and macroscopicproperties. SomecommercialapplicationsofCRPwereannounced attheDenverMeeting,anditisanticipatedthatnewproductsmadebyCRPwill besoononthemarket. The financial support for the symposium from the following organizations is acknowledged: ACS Division of Polymer Chemistry, Inc., Boston Scientific, CSIRO, DSM, Evonik, General Electric, Lubrizol, the National Science Foundation,PPG,RoyalChemicalSocietyandWiley-VCH. g or s. ac KrzysztofMatyjaszewski s.1 b0 u0 12 | http://p12-1100.pr 4DC4ae0rpn0aerFgtmiifetehMntAeovllfeonCnuhUeemniivsetrrysity 00 pril 8, 221/bk-2 Pittsburgh,Pennsylvania15213 A0 EY on oi: 10.1 BrentSumerlin Ld KE2 | DepartmentofChemistry ER201 SouthernMethodistUniversity A B20, 3215DanielAvenue NIch Dallas, Texas75275 Rar OM LIFb): Ae V OF CDate (W NicolayV.Tsarevsky NIn DepartmentofChemistry d by Ublicatio S32o1u5thDerannMieletAhvoednisuteUniversity eu dP a Dallas, Texas75275 o nl w o D xii In Progress in Controlled Radical Polymerization: Mechanisms and Techniques; Matyjaszewski, K., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2012. Chapter 1 Controlled Radical Polymerization: State-of-the-Art in 2011 g or Krzysztof Matyjaszewski* s. c a s.1 ub00 Center for Macromolecular Engineering, Department of ph p://0.c Chemistry, Carnegie Mellon University, 4400 Fifth Avenue, 12 | htt12-110 Pi*tEts-bmuargilh:,[email protected].,eUduSA 00 22 pril 8, 21/bk- A0 EY on oi: 10.1 Ld KE2 | R01 E2 A B20, NIch Thestate-of-the-artofcontrolledradicalpolymerization(CRP) Rar OM in 2011 is presented. Atom transfer radical polymerization, LIFb): stableradicalmediatedpolymerization,anddegeneratetransfer Ae V OF CDate (W ptrraoncsefsesreasr,einthcelumdionsgt oreftveenrsuibseled aCdRdPitipornocferadgumreesn.taCtiRoPn ocpheanins NIn newavenuestonovelmaterialsfromalargerangeofmonomers. d by Ublicatio uDnedtaeirlsetdandsitnrugctunroet-reoancltyivithyelprselaatitotanisnhipas baentdtermceochnatrnoilslteidc eu dP oa polymerization but enables preparation of polymers with wnl complexarchitectures. Correlationofmacromolecularstructure o D with final properties of prepared materials is a prerequisite for creationofnewapplicationsandcommercializationofvarious CRPproducts. ©2012AmericanChemicalSociety In Progress in Controlled Radical Polymerization: Mechanisms and Techniques; Matyjaszewski, K., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2012. Controlled/living radical polymerization (CRP) is among the most rapidly expandingareasofchemistryandpolymerscience(1–5). Theadventofcontrolledradicalpolymerization(CRP)(IUPACrecommends the term reversible-deactivation radical polymerization (RDRP), or controlled reversible-deactivation radical polymerization and discourages using “living radical polymerization”) (6) has opened new avenues to various advanced materialswithpreciselycontrolledmoleculararchitecture. ThedynamicequilibriarequiredinRDRPsystemscanbereachedintwoways (7). Oneapproachemploysreversibledeactivationofpropagatingradicalstoform dormantspeciesthatcanbeintermittentlyre-activatedeitherinthepresenceofa catalyst,asinatomtransferradicalpolymerization,ATRP(8),orspontaneously, g or as in stable radical mediated polymerization, SRMP (with aminoxyl radicals or s. ac organometallicspecies)(9). ThekineticsofSRMPandATRPgenerallyfollowa s.1 ub00 particularpersistentradicaleffect(10). ph p://0.c The second approach employs degenerate transfer between propagating 12 | htt12-110 praodliycmalesriaznadtiodno,rmDTanRtPs,pienccileusd.eTreyvpeicrsailbelex-aamddpilteiosno-ffradgemgeennetraattieo-ntrcahnasfiner-trraandsicfearl 00 pril 8, 221/bk-2 fpoorlyDmTeRriPz,ataionne,xRteArnFaTl osoruiorcdeinoeftrraandsicfearlsraisdincaelcepsoslayrmyebruiztadtioornm(a1n1t).spGeecnieesracllayn, A0 also be activated by Cu-based catalyst, without generation of new chains (12, EY on oi: 10.1 1th3e).nRatAurFeTokfinraedtiiccsalissasnimdiilnarititaotocrosn/tvreanntsifoenraalgRePntbsuatnmdacyansobmeeaticmcoesmdpeapneienddobny Ld KE2 | retardation. ER201 RDRPisamongthemostrapidlydevelopingareasofpolymerscience. They A B20, provide a versatile synthetic tool that enables preparation of new (co)polymers NIch withcontrolledarchitectureandmaterialswithpropertiesthatcanbetargetedfor Rar OM variousadvancedtechnologiesandbiomedicine. Figure1presentsthecumulative LIFb): number of papers published on ATRP, SMRP and RAFT, as well as overall Ae V OF CDate (W RyeDarRsP. T(uhseinggrotwertmhsinlivthinegnuomrcboenrtoroflpleudblriacdaitcioalnpsoinlyamllearirzeaatsioonf)RdDurRinPgrtehfleelcatsstt1h6e NIn increasing level of interest in this field, although currently many papers do not d by Ublicatio wuseellt-ekrnmoswrnel“acteladstsoicR”DteRrmPsinintitlpeosl,yambesrtrascctieonrcke.eywNoervdesr,thaseltehsesy, haacvoenbtiencuoomues eu dP oa increaseinthenumberofpublicationsonCRPcanbenoted. Thisisaccompanied wnl by an increase in the number of patent applications and symposia partially or o D entirelydevotedtoCRP(14–19). Figure1illustratestheresultsofarecentSciFinderScholarsearchusingthe followingterms: controlledradicalpolymnorlivingradicalpolymn(“SUMCRP” inFigure1);ATRPoratomtransfer(radical)polymn(“SUMATRP”,thissearch doesnotincludetermssuchasmetalmediatedormetalcatalyzed(living)radical polymerization);NMPorSFRPornitroxidemediatedpolymnorstablefreepolymn (“SUM SFRP”) and RAFT (“SUM RAFT”). The latter two terms were refined withtermsradicalpolymnandpolymerorpolymn,respectively,sincethesearch coincideswithothercommonchemicaltermssuchasN-methylpyrrolidoneorraft- associated proteins. In summary, over 18,000 papers have been published on various CRP systems since 1995 and more than 11,000 on ATRP. Figure 1 also 2 In Progress in Controlled Radical Polymerization: Mechanisms and Techniques; Matyjaszewski, K., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2012.
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