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AGGREGATION-INDUCED EMISSION (AIE) AGGREGATION- INDUCED EMISSION (AIE) A Practical Guide Edited by J X IANWEI U InstituteofMaterialsResearchandEngineering,AgencyforScience, TechnologyandResearch(A*STAR),Singapore M H C ING UI HUA InstituteofMaterialsResearchandEngineering,AgencyforScience, TechnologyandResearch(A*STAR),Singapore B Z T EN HONG ANG SchoolofScienceandEngineering,ShenzhenKeyLaboratoryofFunctionalAggregateMaterials, TheChineseUniversityofHongKong,Shenzhen,Guangdong,China Elsevier Radarweg29,POBox211,1000AEAmsterdam,Netherlands TheBoulevard,LangfordLane,Kidlington,OxfordOX51GB,UnitedKingdom 50HampshireStreet,5thFloor,Cambridge,MA02139,UnitedStates Copyright©2022ElsevierInc.Allrightsreserved. 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Practitionersandresearchersmustalwaysrelyontheirownexperienceandknowledgeinevaluatingandusing anyinformation,methods,compounds,orexperimentsdescribedherein.Inusingsuchinformationormethods theyshouldbemindfuloftheirownsafetyandthesafetyofothers,includingpartiesforwhomtheyhavea professionalresponsibility. Tothefullestextentofthelaw,neitherthePublishernortheauthors,contributors,oreditors,assumeanyliability foranyinjuryand/ordamagetopersonsorpropertyasamatterofproductsliability,negligenceorotherwise,or fromanyuseoroperationofanymethods,products,instructions,orideascontainedinthematerialherein. ISBN:978-0-12-824335-0 ForinformationonallElsevierpublications visitourwebsiteathttps://www.elsevier.com/books-and-journals Publisher:MatthewDeans AcquisitionsEditor:KaylaDosSantos EditorialProjectManager:IsabellaC.Silva ProductionProjectManager:AnithaSivaraj CoverDesigner:MarkRogers TypesetbySTRAIVE,India Contributors MassimoCametti DepartmentofChemistry, ZhiyuanGao StateKeyLaboratoryofMedicinal MaterialsandChemicalEngineering“Giulio ChemicalBiology,KeyLaboratoryofBioactive Natta”,PolitecnicodiMilano,Milano,Italy Materials,MinistryofEducation,andCollege SijieChen MingWaiLauCentreforReparative ofLifeSciences,NankaiUniversity,Tianjin, China Medicine,KarolinskaInstitutet,HongKong, China XiangyuGe PCFMLab,GDHPPCLab, XiaojieChen PCFMLab,GDHPPCLab, GuangdongEngineeringTechnologyResearch CenterforHigh-performanceOrganicand GuangdongEngineeringTechnologyResearch PolymerPhotoelectricFunctionalFilms,State CenterforHigh-performanceOrganicand PolymerPhotoelectricFunctionalFilms,State KeyLaboratoryofOEMT,SchoolofChemistry, SunYat-senUniversity,Guangzhou,China KeyLaboratoryofOEMT,SchoolofChemistry, SunYat-senUniversity,Guangzhou,China MasayukiGon DepartmentofPolymer ZhenguoChi PCFMLab,GDHPPCLab, Chemistry,GraduateSchoolofEngineering, GuangdongEngineeringTechnologyResearch KyotoUniversity,Kyoto,Japan CenterforHigh-performanceOrganicand PengboHan StateKeyLaboratoryof PolymerPhotoelectricFunctionalFilms,State LuminescentMaterialsandDevices, KeyLaboratoryofOEMT,SchoolofChemistry; GuangdongProvincialKeyLaboratoryof SchoolofMaterialsScienceandEngineering, LuminescencefromMolecularAggregates,AIE SunYat-senUniversity,Guangzhou,China Institute,CenterforAggregation-Induced MingHuiChua InstituteofMaterialsResearch Emission,SouthChinaUniversityof andEngineering,A*STAR(AgencyforScience, Technology(SCUT),Guangzhou,China TechnologyandResearch),Singapore, KyoheiHisano DepartmentofApplied Singapore Chemistry,RitsumeikanUniversity,Kusatsu, YoshikiChujo DepartmentofPolymer Japan Chemistry,GraduateSchoolofEngineering, YuningHong DepartmentofChemistryand KyotoUniversity,Kyoto,Japan Physics,LaTrobeInstituteforMolecular DanDing StateKeyLaboratoryofMedicinal Science,LaTrobeUniversity,Melbourne,VIC, Australia ChemicalBiology,KeyLaboratoryofBioactive Materials,MinistryofEducation,andCollege RongrongHu StateKeyLaboratoryof ofLifeSciences,NankaiUniversity,Tianjin, LuminescentMaterialsandDevices, China GuangdongProvincialKeyLaboratoryof YongQiangDong BeijingKeyLaboratoryof LuminescencefromMolecularAggregates,AIE Institute,CenterforAggregation-Induced EnergyConversionandStorageMaterials, CollegeofChemistry,BeijingNormal Emission,SouthChinaUniversityof Technology(SCUT),Guangzhou,China University,Beijing,China ZoranDzˇoli(cid:1)c RuđerBosˇkovi(cid:1)cInstitute,Zagreb, YangHu StateKeyLaboratoryofLuminescent MaterialsandDevices,GuangdongProvincial Croatia ix x Contributors KeyLaboratoryofLuminescencefrom DepartmentofChemistry,Tsinghua MolecularAggregates,AIEInstitute,Centerfor University,Beijing,China Aggregation-InducedEmission,SouthChina SupattraPanthai DepartmentofApplied UniversityofTechnology(SCUT),Guangzhou, Chemistry,RitsumeikanUniversity,Kusatsu, China Japan ShunichiroIto DepartmentofPolymer SurajKumarPathak CollegeofMaterials Chemistry,GraduateSchoolofEngineering, ScienceandEngineering,ShenzhenUniversity, KyotoUniversity,Kyoto,Japan Shenzhen,China ChuenKam MingWaiLauCentrefor QianPeng SchoolofChemicalSciences, ReparativeMedicine,KarolinskaInstitutet, UniversityofChineseAcademyofSciences, HongKong,China Beijing,China BingShiLi KeyLaboratoryofNewLithium-Ion AndreaPucci DepartmentofChemistryand BatteryandMesoporousMaterial,Collegeof IndustrialChemistryoftheUniversityofPisa, ChemistryandEnvironmentalEngineering, Pisa,Italy ShenzhenUniversity,Shenzhen,China AnjunQin StateKeyLaboratoryof HongkunLi LaboratoryofAdvanced LuminescentMaterialsandDevices, OptoelectronicMaterials,CollegeofChemistry, GuangdongProvincialKeyLaboratoryof ChemicalEngineeringandMaterialsScience, LuminescencefromMolecularAggregates,AIE SoochowUniversity,Suzhou,China Institute,CenterforAggregation-Induced MengLi CenterforAIEResearch,Shenzhen Emission,SouthChinaUniversityof University,Shenzhen;ShenzhenInstituteof Technology(SCUT),Guangzhou,China AggregateScienceandTechnology,Schoolof SoheilaSabouri DepartmentofChemistryand ScienceandEngineering,TheChinese Physics,LaTrobeInstituteforMolecular UniversityofHongKong, Science,LaTrobeUniversity,Melbourne,VIC, Shenzhen,Guangdong,China Australia XiangyuLi InstituteofFineChemicals,East MasakiShimizu FacultyofMolecular ChinaUniversityofScienceandTechnology, ChemistryandEngineering,KyotoInstituteof Shanghai,China Technology,Kyoto,Japan Guey-ShengLiou InstituteofPolymerScience ZhigangShuai MOEKeyLaboratoryofOrganic andEngineering,NationalTaiwanUniversity, OptoElectronicsandMolecularEngineering, Taipei,Taiwan DepartmentofChemistry,Tsinghua YantingLyu InstituteofFineChemicals,East University,Beijing,China ChinaUniversityofScienceandTechnology, YueSi BeijingKeyLaboratoryofEnergy Shanghai,China ConversionandStorageMaterials,Collegeof JuMei KeyLaboratoryforAdvancedMaterials, Chemistry,BeijingNormalUniversity,Beijing, FeringaNobelPrizeScientistJointResearch China Center,FrontiersScienceCenterfor KazuoTanaka DepartmentofPolymer MateriobiologyandDynamicChemistry,Joint Chemistry,GraduateSchoolofEngineering, InternationalResearchLaboratoryforPrecision KyotoUniversity,Kyoto,Japan ChemistryandMolecularEngineering, BenZhongTang SchoolofScienceand InstituteofFineChemicals,Schoolof Engineering,ShenzhenKeyLaboratoryof Chemistry&MolecularEngineering,East FunctionalAggregateMaterials,TheChinese ChinaUniversityofScience&Technology, UniversityofHongKong, Shanghai,P.R.China Shenzhen,Guangdong,China QiOu MOEKeyLaboratoryofOrganic HeTian KeyLaboratoryforAdvanced OptoElectronicsandMolecularEngineering, Materials,FeringaNobelPrizeScientistJoint xi Contributors ResearchCenter,FrontiersScienceCenterfor CenterforHigh-performanceOrganicand MateriobiologyandDynamicChemistry,Joint PolymerPhotoelectricFunctionalFilms,State InternationalResearchLaboratoryforPrecision KeyLaboratoryofOEMT,SchoolofChemistry, ChemistryandMolecularEngineering, SunYat-senUniversity,Guangzhou,China InstituteofFineChemicals,Schoolof BichengYao DepartmentofChemistryand Chemistry&MolecularEngineering,East Physics,LaTrobeInstituteforMolecular ChinaUniversityofScience&Technology, Science,LaTrobeUniversity,Melbourne,VIC, Shanghai,P.R.China Australia OsamuTsutsumi DepartmentofApplied Hung-JuYen InstituteofChemistry,Academia Chemistry,RitsumeikanUniversity,Kusatsu, Sinica,Taipei,Taiwan Japan LihuiZhang StateKeyLaboratoryof DongWang CenterforAIEResearch,Shenzhen LuminescentMaterialsandDevices, University,Shenzhen,China GuangdongProvincialKeyLaboratoryof FeiWang MingWaiLauCentreforReparative LuminescencefromMolecularAggregates,AIE Medicine,KarolinskaInstitutet,HongKong, Institute,CenterforAggregation-Induced China Emission,SouthChinaUniversityof JiaWang StateKeyLaboratoryofLuminescent Technology(SCUT),Guangzhou,China MaterialsandDevices,GuangdongProvincial YiZhang PCFMLab,GDHPPCLab, KeyLaboratoryofLuminescencefrom GuangdongEngineeringTechnologyResearch MolecularAggregates,AIEInstitute,Centerfor CenterforHigh-performanceOrganicand Aggregation-InducedEmission,SouthChina PolymerPhotoelectricFunctionalFilms,State UniversityofTechnology(SCUT),Guangzhou, KeyLaboratoryofOEMT,SchoolofChemistry, China SunYat-senUniversity,Guangzhou,China QiWang InstituteofFineChemicals,EastChina YouhengZhang InstituteofFineChemicals, UniversityofScienceandTechnology, EastChinaUniversityofScienceand Shanghai,China Technology,Shanghai,China AlexY.H.Wong MingWaiLauCentrefor YucongZhang BeijingKeyLaboratoryof ReparativeMedicine,KarolinskaInstitutet, EnergyConversionandStorageMaterials, HongKong,China CollegeofChemistry,BeijingNormal JianweiXu InstituteofMaterialsResearchand University,Beijing,China Engineering,A*STAR(AgencyforScience, JuanZhao SchoolofMaterialsScienceand TechnologyandResearch),Singapore, Engineering,SunYat-senUniversity, Singapore Guangzhou,China ChuluoYang CollegeofMaterialsScienceand HuiZhou InstituteofMaterialsResearchand Engineering,ShenzhenUniversity,Shenzhen, Engineering,A*STAR(AgencyforScience, China TechnologyandResearch),Singapore, ZhanYang PCFMLab,GDHPPCLab, Singapore GuangdongEngineeringTechnologyResearch QiangZhu InstituteofMaterialsResearchand CenterforHigh-performanceOrganicand Engineering,A*STAR(AgencyforScience, PolymerPhotoelectricFunctionalFilms,State TechnologyandResearch),Singapore, KeyLaboratoryofOEMT,SchoolofChemistry, Singapore SunYat-senUniversity,Guangzhou,China Wei-HongZhu InstituteofFineChemicals,East ZhiyongYang PCFMLab,GDHPPCLab, ChinaUniversityofScienceandTechnology, GuangdongEngineeringTechnologyResearch Shanghai,China Preface The discovery of aggregation-induced applications. Thereafter, chiral AIEgens with emission(AIE)in2001hasservedasagame circularly polarized luminescence and helical changerinthedevelopmentandapplication self-assembly properties are described in of luminogenic functional materials. Funda- Chapter 4, followed by AIE supramolecular mentalunderstandingofphotophysicalpro- gelsystemsinChapter5. cessesandpropertiesinorganicluminogens Thesecondpartofthebookseekstoshow- has been reshaped, creating vast opportuni- casetheapplicationdiversityandusefulnessof ties for a wide range of applications of AIE AIEgens.AIEgenscanbebroadlycategorized luminogens (AIEgens). AIE has effectively intofourkeydomainsintermsoftheirmainap- overcome the limitations of aggregation- plications:(i)stimuli-responsiveAIEsystems, caused quenching (ACQ) commonly found (ii) optoelectronics, (iii) biomedical sensing, intraditionalluminogens.Thisnotonlycon- and (iv) chemical sensing. The subsequent tributes to improvement in material perfor- chaptersarethereforearrangedinaccordance mance for existing applications but also with their applications in the respective leads to the emergence of new applications. domains.Forstimuli-responsiveAIEsystems, Therefore, research interests and efforts in Chapter6discussesmechanochromicAIEgens, the area of AIE have soared over the past whereasChapter7reviewsAIEgenswithpho- two decades, with an exponential growth tochromicandthermochromicproperties. of scientific publications and citations, serv- AIEgensareexcellentcandidatesforopto- ing as a testament to the usefulness of electronic applications, notably organic AIEgens. This book, therefore, aims to pro- light-emitting diodes (OLEDs) and liquid videaholisticcoverageofbothfundamental crystal (LC) optical displays, due to their principlesandapplicationsofAIEgens,cov- amplification of luminescence intensities in eringthekeyscientificprogressesintheAIE the solid states. Chapters 8 and 9 introduce topic at an introductory-to-intermediate pure organic AIEgens that exhibit (aggrega- level, suitable for a wide range of scientific tion and crystallization-induced) phospho- and academic audiences, both within and rescence and thermally activated delayed outside the AIE research fraternity. fluorescence (TADF) properties, respec- This book begins with the introduction tively, both of which exhibit important of fundamental concepts, principles, and solid-state luminescence properties particu- mechanisms of AIE in Chapter 1. To date, a larly for the development of OLEDs. This large number of novel AIEgens have been leadsustoChapter10,inwhichtheapplica- designed and synthesized, and therefore the tion of AIEgens in OLEDs is summarized. firstpartofthebookseekstodisplaythestruc- TheuseofAIEgensinothernotableoptoelec- tural diversities of AIEgens. Chapter 2 high- tronic applications such as LC optical dis- lights novel AIEgens with boron complexes plays, electrofluorochromic devices, and while Chapter 3 summarizes numerous AIE- photovoltaics is discussed separately in activepolymersdevelopedthusfarforvarious Chapters 11–13. xiii xiv Preface Next, the book concentrates on AIEgens sensor to detect analytes in the vapor state for biomedical applications, including bio- is discussed in Chapter 18. Thereafter, sensing and bioimaging, diagnostics, the- Chapter 19 highlights the use of AIEgens in rapy, and drug delivery. AIEgens may be sensing foodstuff hazards as well as a fluo- directly used as molecular fluorescent rescent thermometer. Finally, Chapter 20 probes (mainly for biosensing and imaging) summarizes the luminescence mechanism or be further prepared as fluorescent of AIEgens utilizing computational simula- nanoparticles (FNPs) and bioconjugates to tion and modeling methods, which provide enhance luminescence intensity, sensitivity, another way to have in-depth and intrinsic and biocompatibility. The use of AIE-active understanding ofthe natureof AIE. molecular probes, FNPs, and bioconjugates Through this book, it is envisaged that foraspectrumofdifferentbiomedicalappli- readers will gain knowledge and under- cations is collectively discussed in Chapters standing about not only the fundamental 14–16,respectively. principles of AIE but more importantly In addition to biosensing, chemical sens- how AIE luminogens can be incorporated ing encompasses environmental monitoring in various molecular and polymeric mate- of harmful substances to safeguard public rials to specifically cater to targeted needs health and the detection of trace chemicals and applications. for product quality assurance. Chapter 17 Finally, the editors wish to express their thereforesummarizesAIE-basedfluorescent immense appreciation to all authors for chemosensors for explosive detection while their dedicated efforts in contributing the development of an AIE-based vapor high-quality work to thisbook.