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Advances in Organic Crystal Chemistry: Comprehensive Reviews 2015 PDF

699 Pages·2015·30.165 MB·English
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Editors Rui Tamura · Mikiji Miyata Advances in Organic Crystal Chemistry Comprehensive Reviews 2015 Advances in Organic Crystal Chemistry Rui Tamura • Mikiji Miyata Editors Advances in Organic Crystal Chemistry Comprehensive Reviews 2015 123 Editors RuiTamura MikijiMiyata GraduateSchoolofHuman TheInstituteofScientific andEnvironmentalStudies andIndustrialResearch KyotoUniversity OsakaUniversity Kyoto,Japan Osaka,Japan ISBN978-4-431-55554-4 ISBN978-4-431-55555-1 (eBook) DOI10.1007/978-4-431-55555-1 LibraryofCongressControlNumber:2015947134 SpringerTokyoHeidelbergNewYorkDordrechtLondon ©SpringerJapan2015 Thisworkissubjecttocopyright.AllrightsarereservedbythePublisher,whetherthewholeorpartof thematerialisconcerned,specificallytherightsoftranslation,reprinting,reuseofillustrations,recitation, broadcasting,reproductiononmicrofilmsorinanyotherphysicalway,andtransmissionorinformation storageandretrieval,electronicadaptation,computersoftware,orbysimilarordissimilarmethodology nowknownorhereafterdeveloped. Theuseofgeneraldescriptivenames,registerednames,trademarks,servicemarks,etc.inthispublication doesnotimply,evenintheabsenceofaspecificstatement,thatsuchnamesareexemptfromtherelevant protectivelawsandregulationsandthereforefreeforgeneraluse. Thepublisher,theauthorsandtheeditorsaresafetoassumethattheadviceandinformationinthisbook arebelievedtobetrueandaccurateatthedateofpublication.Neitherthepublishernortheauthorsor theeditorsgiveawarranty,expressorimplied,withrespecttothematerialcontainedhereinorforany errorsoromissionsthatmayhavebeenmade. Printedonacid-freepaper SpringerJapanKKispartofSpringerScience+BusinessMedia(www.springer.com) Preface Forthelastdecade,thetopicsoforganiccrystalchemistryhavebecomediversified, and each topic has been substantially advanced in concert with the rapid devel- opment of various analytical and measurement techniques for solid-state organic materials. The aim of this book is to systematically summarize and record the recent notable advances in various topics of organic crystal chemistry involving liquid crystals and organic–inorganic hybrid materials that have been achieved mainly in the last 5 years or so. The summaries and records contained herein are by invited members of the Division of Organic Crystals in the Chemical Society of Japan (CSJ) and prominent invited authors from abroad. In this first volume, most of the authors were plenary or invited speakers at the Joint Congress of the 11thInternationalWorkshopon theCrystalGrowthofOrganicMaterials(CGOM 11) and the Asian Crystallization Technology Symposium 2014 (ACTS-2014) held in Nara, Japan, 17–20 June 2014. The 35 papers contributed to this volume are roughly classified into eight categories: (1) Nucleation and Crystal Growth, (2)CrystalStructureDeterminationandMolecularOrbitalCalculation,(3)Crystal Structure, (4) Polymorphism, (5) Chirality, (6) Solid-State Reaction, (7) Photo- inducedBehavior,and(8)ElectricandMagneticProperties. The Division of Organic Crystals was founded in CSJ in 1997 as a stimulus for research in organiccrystal chemistry in Japan. The first presidentwas the late ProfessorFumioToda,whoperformedagreatservicein establishingthedivision. Today’sactivitiesconsistoftwo annualdomesticconferences(theSymposiumon OrganicCrystals in the autumnand the AnnualSpringMeeting of CSJ at the end ofMarch)andbiannualpublicationoftheOrganicCrystalsDivisionNews Letter. Wehopethatthiseditedvolumewillbepublishedperiodically,atleastevery5years, as one of the division’s activities through contributions by prominent authors in Japanandfromabroad. v vi Preface Finally,weeditorswouldliketoexpressoursincerestgratitudetoallauthorsfor theirgreatcontributionstoAdvancesinOrganicCrystalChemistry:Comprehensive Reviews2015. Kyoto,Japan RuiTamura Suita,Japan MikijiMiyata February2015 Contents PartI NucleationandCrystalGrowth 1 PhotochemicallyInducedCrystallizationofProtein ................... 3 TetsuoOkutsu 2 Ultrasonication-ForcedAmyloidFibrillationofProteins.............. 15 MasatomoSo,YuichiYoshimura,andYujiGoto 3 InSituSolid-StateNMRStudiesofCrystallizationProcesses......... 31 KennethD.M.Harris, ColanE.Hughes, andP.AndrewWilliams 4 NucleationandCrystalGrowthinLimitedCrystallizationField..... 55 HiroshiTakiyama 5 ParticleEngineeringwithCO -ExpandedSolvents:The 2 DELOSPlatform ........................................................... 73 PaulaE.Rojas,SantiSala,ElisaElizondo,JaumeVeciana, andNoraVentosa 6 AddressingtheStochasticityofNucleation:PracticalApproaches... 95 NadineCandoni, ZoubidaHammadi, RomainGrossier, ManuelIldefonso, ShuhengZhang, RogerMorin, andStéphaneVeesler 7 MetastabilityofSupersaturatedSolutionandNucleation............. 115 NoriakiKubota,MasanoriKobari,andIzumiHirasawa PartII CrystalStructureDeterminationandMOCalculation 8 StructureDeterminationofOrganicMolecularSolids from Powder X-Ray Diffraction Data: Current OpportunitiesandStateoftheArt ....................................... 141 KennethD.M.HarrisandP.AndrewWilliams vii viii Contents 9 Magnetically Oriented Microcrystal Arrays andSuspensions: ApplicationtoDiffractionMethods andSolid-StateNMRSpectroscopy ...................................... 167 TsunehisaKimura 10 AnalysisofIntermolecularInteractionsby AbInitioMolecularOrbitalCalculations:Importancefor StudyingOrganicCrystals ................................................ 187 SeijiTsuzuki PartIII CrystalStructure 11 Construction of Aromatic Folding Architecture: UtilizationofUreyleneandIminodicarbonylLinkers.................. 203 ShigeoKohmoto 12 CrystalEngineering ofCoordinationNetworksUsing Multi-interactiveLigands.................................................. 223 YumiYakiyama,TatsuhiroKojima,andMasakiKawano 13 Azacalixarene:AnEver-GrowingClassintheCalixareneFamily.... 241 HirohitoTsueandRyuseiOketani PartIV Polymorphism 14 PolymorphisminMolecularCrystalsandCocrystals.................. 265 SrinivasuluAitipamula 15 Hydration/DehydrationPhaseTransitionMechanism inOrganicCrystalsInvestigatedbyAbInitioCrystal StructureDeterminationfromPowderDiffractionData .............. 299 KotaroFujiiandHidehiroUekusa 16 CharacteristicsofCrystalTransitionsAmongPseudopolymorphs... 317 YokoSugawara 17 AnomalousFormationPropertiesofNicotinamideCo-crystals....... 337 Si-WeiZhangandLianYu 18 IsothermalCrystallizationofPharmaceuticalGlasses: TowardPredictionofPhysicalStabilityofAmorphous DosageForms............................................................... 355 KohsakuKawakami PartV Chirality 19 Twofold Helical Molecular Assemblies in Organic Crystals:ChiralityGenerationandHandednessDetermination...... 371 MikijiMiyataandIchiroHisaki Contents ix 20 ChiralDiscriminationintheSolidState:Applications toResolutionandDeracemization........................................ 393 GérardCoquerel 21 HowtoUsePasteur’sTweezers........................................... 421 RichardM.Kellogg 22 TotalResolutionofRacematesbyDynamicPreferential Crystallization .............................................................. 445 MasamiSakamotoandTakashiMino 23 ChiralRecognitionbyInclusionCrystalsofAmino-Acid DerivativesHavingTritylGroups ........................................ 463 MotohiroAkazome PartVI Solid-StateReaction 24 ReactionsandOrientationalControlofOrganicNanocrystals....... 485 ShujiOkadaandHidetoshiOikawa 25 TopochemicalPolymerizationofAminoAcidN-Carboxy AnhydridesinCrystallineState........................................... 503 HitoshiKanazawa 26 TopochemicalPolymerizationsandCrystalCross-Linking ofMetalOrganicFrameworks............................................ 517 KazukiSada,TakumiIshiwata,andKentaKokado PartVII PhotoinducedBehavior 27 Photoinduced Mechanical Motion of Photochromic CrystallineMaterials....................................................... 533 SeiyaKobatakeandDaichiKitagawa 28 Photoinduced Reversible Topographical Changes onPhotochromicMicrocrystallineSurfaces............................. 549 KingoUchida 29 Luminescence Modulation of Organic Crystals byaSupramolecularApproach........................................... 569 NorimitsuTohnai 30 Solid-StateCircularlyPolarizedLuminescenceofChiral SupramolecularOrganicFluorophore................................... 587 YoshitaneImai PartVIII ElectricandMagneticProperties 31 Relationship Between the Crystal Structures andTransistorPerformanceofOrganicSemiconductors.............. 607 YoshiroYamashita

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