Table Of ContentEditors
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
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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
