Handbook of Macrocyclic Supramolecular Assembly

1704 Pages·2020·94.772 MB·English

by  Yu Liu, Yong Chen, Heng-Yi Zhang

Yu Liu
Yong Chen
Heng-Yi Zhang
Editors
Handbook of
Macrocyclic
Supramolecular
Assembly
Handbook of Macrocyclic Supramolecular
Assembly
(cid:129) (cid:129)
Yu Liu Yong Chen Heng-Yi Zhang
Editors
Handbook of Macrocyclic
Supramolecular Assembly
With1098Figuresand32Tables
Editors
YuLiu YongChen
CollegeofChemistry,StateKey CollegeofChemistry,StateKey
LaboratoryofElemento-Organic LaboratoryofElemento-Organic
Chemistry Chemistry
NankaiUniversity NankaiUniversity
Tianjin,China Tianjin,China
CollaborativeInnovation CollaborativeInnovation
CenterofChemicalScienceand CenterofChemicalScienceand
Engineering(Tianjin) Engineering(Tianjin)
Tianjin,China Tianjin,China
Heng-YiZhang
CollegeofChemistry,StateKey
LaboratoryofElemento-Organic
Chemistry
NankaiUniversity
Tianjin,China
CollaborativeInnovation
CenterofChemicalScienceand
Engineering(Tianjin)
Tianjin,China
ISBN978-981-15-2685-5 ISBN978-981-15-2686-2(eBook)
ISBN978-981-15-2687-9(printandelectronicbundle)
https://doi.org/10.1007/978-981-15-2686-2
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Foreword
As a result of the significant development of supramolecular chemistry, the Nobel
Prizes were awarded to supramolecular chemists in 1987 (Donald J. Cram, Jean-
Marie Lehn, Charles J. Pedersen) and 2016 (Jean-Pierre Sauvage, Sir J. Fraser
Stoddart, Bernard L. Feringa). Within the field of supramolecular chemistry there
isanincreasinginterestfocusedonthesupramolecularassembliesbasedonmacro-
cycles, including ionic crown ethers, ionic macrocyclic arenes, cyclodextrins,
cucurbiturils,etc.,andthesemacrocyclesareextensivelyusedasnotonlyexcellent
receptorsformolecularrecognitionbutalsoconvenientbuildingblockstoconstruct
nanostructuredfunctionalmaterials,especiallybioactivematerials.
Looking back, many scientists made a solid foundation for the development of
macrocyclicsupramolecularassembly.Atthesametime,wearealsodelightedtosee
that a group of young chemists have grown and started to show their prominent
abilitiesinthisarea.Theseyearswitnessedasignificantharvestinthemacrocyclic
supramolecular chemistry. However, we believe that, with the joint efforts of all
supramolecularchemists,theexcitingfindingsareonlybeginningtobediscovered.
To further present these research achievements, Springer Nature decided to
publishtheHandbookofMacrocyclicSupramolecularAssembly,andIwasinvited
toactasaneditorofthishandbookatthetimeofThe100thAnniversaryofNankai
University.Themainpurposeofthehandbookistoprovideeducators,scientists,and
graduateandundergraduatestudentswitharelativelycomprehensivesetofknowl-
edge and recent developments covering macrocycle-based supramolecular chemis-
try,biochemistry,functionalmaterial,andnanotechnology.Iwishthatthepublishing
of this handbook will be helpful to the chemists who are interested in the
v
vi Foreword
macrocyclic supramolecular chemistry. I also wish to thank the editorial team at
SpringerNatureandco-workers,inparticularMs.HaiqinDong,Ms.LijuanWang,
andMr.StephenYeung,fortheirtremendouswork.Finally,itismyhonortothank
all the contributors of this handbook who presented so many excellent works and
madethepublicationofthehandbooksuccessful.
CollegeofChemistry,StateKeyLaboratory
ofElemento-OrganicChemistry
CollaborativeInnovationCenterof YuLiu
ChemicalScienceandEngineering
NankaiUniversity
Preface
Fromthe1960stothe1980s,Pedersenreportedthediscoveryofcrownethersashost
molecules, Cram incorporated host-guest chemistry, and Lehn created supramolec-
ular chemistry. From then on, supramolecular chemistry becomes one of the most
popularandfastestgrowingareasofchemistry,leadingtonumerousachievementsin
molecularrecognition,molecularassembly,molecularmachine,andsoon.Mostof
these works are based on macrocyclic compounds, and these macrocycles act as
goodreceptorsformolecularrecognitionandconvenientbuildingblocksformolec-
ularassemblyandmolecularmachine.Therefore,providingacomprehensivesetof
knowledge on recent developments of macrocycle-based supramolecular system,
especiallyfunctionalsupramolecularassembly,toeducators,scientists,andstudents
whoareinterestedinsupramolecularchemistrybecomesnecessary.
With this aim, Prof. Yu Liu, Prof. Yong Chen, and Prof. Heng-Yi Zhang from
NankaiUniversityjointlyeditedahandbookofmacrocyclicsupramolecularassem-
bly, which is now being published by Springer Nature. The handbook mainly
focuses on works in the field of macrocyclic supramolecular assemblies, with an
emphasisontheirconstruction,structuralcharacters,andbiologicalfunctions.All59
chapters of the handbook cover a wide variety of topics on macrocyclic supramo-
lecular assemblies including: (1) construction and structure of macrocyclic supra-
molecularassembly(keybuildingblock,constructionmethod,structuralmotif,and
stimuli responsive control); (2) approach and technology (controllable synthesis,
molecularrecognition,spectralandthermodynamicstudy,supramolecularassembly
atinterface, orthogonalself-assembly,supramolecularorganicframework,molecu-
lar induced aggregation, theoretical calculation, and molecular simulation); (3)
application(chemicalandbiologicalsensing,theranostictool,molecule/ionchannel,
drug/genedelivery,supramolecule-assistedbiomoleculeproduction,supramolecule-
assistedtransmembranetransport,supramolecule-assistedimmunityregulation,and
supramolecule-basedmedicinaldrug.).
Eachchapterinthishandbookiswrittenbyactiveexpertsintheresearchfieldof
macrocyclicsupramolecularassemblyandhasahighacademiclevel.Togetherthey
formahandbookthatmaybecomeveryimportantinthebibliographyofsupramo-
lecular chemistry. I am glad to participate in this project by recommending this
vii
viii Preface
handbook to scientists interested in the research of supramolecular assembly and
application,toengineers interestedintheuseofsupramolecular techniques,andto
undergraduateandgraduatestudentswhointendtobegintheirresearchinsupramo-
lecularchemistry.
NankaiUniversity
Jin-PeiCheng
Contents
Volume 1
PartI SupramolecularAssembliesBasedonCrownEthersand
Cyclophanes .............................................. 1
1 Water-SolubleAromaticCrownEthers ..................... 3
LingChenandYuLiu
2 PolypseudorotaxanesConstructedbyCrownEthers ........... 27
Hong-GuangFu,YongChen,andYuLiu
3 Host-GuestChemistryofaTetracationicCyclophane,Namely,
Cyclobis(paraquat-p-phenylene) .......................... 49
HaoLi,TianyuJiao,andLiboShen
4 MechanicallySelf-LockedMolecules ....................... 83
Sheng-HuaLi,YongChen,andYuLiu
5 PhotoluminescentCrownEtherAssembly ................... 107
YanZhou,Bang-TunZhao,andYuLiu
PartII SupramolecularAssembliesBasedonMacrocyclic
Arenes .................................................. 137
6 Triptycene-DerivedMacrocyclicArenes ..................... 139
YingHanandChuan-FengChen
7 EmergingMacrocyclicArenesRelatedtoCalixarenesand
Pillararenes ........................................... 181
DihuaDai,Jia-RuiWu,andYing-WeiYang
8 SupramolecularMedicineofDiverseCalixareneDerivatives .... 201
JieGaoandDong-ShengGuo
ix
x Contents
9 PreparationofBiosensorBasedonSupermolecular
Recognization ......................................... 231
JingjingJiang,XinyiLin,andGuowangDiao
10 ApplicationofAnion-πInteractiononSupramolecular
Self-Assembly ......................................... 253
De-XianWang
11 FunctionalRotaxanes ................................... 277
Cai-XinZhao,QiZhang,GáborLondon,andDa-HuiQu
12 Biphen[n]arenes:SynthesisandHost–GuestProperties ......... 311
BinLi,YiliangWang,andChunjuLi
13 Pillararene-BasedSupramolecularPolymer .................. 341
XuanWu,YongChen,andYuLiu
PartIII SupramolecularAssembliesBasedonCyclodextrins ..... 383
14 FunctionalizedCyclodextrinsandTheirApplicationsin
Biodelivery ........................................... 385
JiangLiu,PengYu,MatthieuSollogoub,andYongminZhang
15 CyclodextrinHybridInorganicNanocompositesforMolecular
Recognition,SelectiveAdsorption,andDrugDelivery .......... 425
WentingLiangandShaominShuang
16 PhotoresponsiveSupramolecularPolymersBasedonHost-Guest
Interactions ........................................... 451
FanGuandXiangMa
17 Cyclodextrin-BasedSupramolecularHydrogel ............... 483
QianZhao,YongChen,andYuLiu
18 SupramolecularPhotochirogenesiswithCyclodextrin .......... 509
JiabinYao,YoshihisaInoue,andChengYang
19 ConstructionandApplicationsofCyclodextrinPolymersin
Biology ............................................... 537
Yao-HuaLiu,Heng-YiZhang,andYuLiu
20 ConstructionandBiomedicalApplicationofMagnetic
SupramolecularAssemblies .............................. 559
QilinYu,YongChen,BingZhang,Ying-MingZhang,andYuLiu
21 SupramolecularAssemblyConstructedfromMulti-charged
Cyclodextrin-InducedAggregation ......................... 573
Pei-YuLi,YongChen,andYuLiu