Inorganic-Organic Hybrid Materials

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1 Inorganic-rganic Hybrid Materials Bressanone Sept Hybrid Materials 1 Bressanone Sept Hybrid Materials 2 1

2 Composites Hybrid Materials cm CLASSICAL CMPSITES µm Property Improvement: mechanical stability thermal stability photochemical stability nm Hybrid Materials From Molecules to anobuilding Blocks Various properties possible depending on precursors and processing Bressanone Sept Hybrid Materials 3 Hybrid Materials Composite Material Macroscopic phases Compound 1 Compound 2 Hybrid Material Molecular or nanoscale building blocks The goal is to create materials with specific combinations of properties by combining different molecular building blocks in various ratios and by controlling their mutual arrangement Control at the nanolevel Bressanone Sept Hybrid Materials 4 2

3 Homogeneity vs. Problems: scatters light, mechanical properties, etc Control over homogeneity: precursor selection (functional group) reaction conditions: kinetics, solvent, etc. interactions between the components Bressanone Sept Hybrid Materials 5 Typical Properties of rganic and Inorganic Materials Properties ature of bonds T g Thermal stability Density efractive index Mechanical properties Hydrophobicity Electronic and magnetic properties Processability rganic materials (polymers) covalent [C C], van der Waals, H-bonding low low (except polyimides) low low elastic flexible rubbery (depending on T g ) hydrophilic or hydrophobic insulating to conductive non-magnetic at low temperatures and pressures (molding, casting, etc.) Inorganic materials (glass, ceramics) ionic or covalent high high high high hard strong brittle hydrophilic insulating to semiconductors magnetic at high temperatures and/or pressures (sintering, glass forming) Bressanone Sept Hybrid Materials 6 3

4 anolego Form Function Geometry of the linkage Connectivity Kind of linkage Bressanone Sept Hybrid Materials 7 Inorganic Building Blocks anolego: Building Blocks Connecting Blocks H 2 C Ti Ti X Y Mechanical, optical, electrical, magnetical properties eduction of the crosslinking density, coupling sites between inorganic / organic components rganic Building Blocks A Functional groups, crosslinking, polymerizability Flexibility, elasticity, processability H 2 C C H 2 H 2 C C H 2 Bressanone Sept Hybrid Materials 8 4

5 Polymerization / Polycondensation anolego: Linking the Building Blocks CH 3 C CH 3 C CH 3 C H H H + H 2 H 2 H H Sol-Gel-Process + H2 H H H H - H 2 H H H a H + H H H H H H H Self-rganization Zn( 3 ) 2 + H Zn 4 (terephthalate) 6 H Bressanone Sept Hybrid Materials 9 anolego: Critical Issues Homogeneous distribution of the building blocks in the material Stable distribution: no microphase separation Interaction between the two components Structure-property relationships Inclusion of functionalities Tailoring of molecular structure nanostructure microstructure (= hierarchical structure design) Bressanone Sept Hybrid Materials 10 5

6 Precursors Molecular precursors Clusters (nano-building blocks, BB) Alkoxysilyl-substituted organic polymers Pre-formed nanostructures Classes of sol-gel hybrid materials Physically entrapped components Functionalized inorganic networks Interpenetrating networks Dual networks Bressanone Sept Hybrid Materials 11 Molecular Precursors etwork Modifiers (non-reactive organic groups) () 3 () 3 CH 3 () 3 Precursors with Functional rganic Groups () 3 () 3 () 3 Ti polymerizable organic groups inorganic-organic hybrid polymers + HS-() 3 ()3 (Et) 3 H H H 2 () 3 TiS 3 (Co-phthalocyanine) groups with other organic functions 2 Bressanone Sept Hybrid Materials 12 6

7 ano Building Blocks: Polyhedral ligomeric lsesquioxanes (PSS) Bressanone Sept Hybrid Materials 13 ano Building Blocks: Functionalized Metal xide Clusters Ti (Et) 24 (Pr) 8 (same with CH 2 CH 2 C()C(Me)=CH 2 ) Zr 6 4 (H) 4 (methacrylate) 12 covalent interaction [(BuSn) (H) 6 ] 2+ 2 methacrylate - [W ( 2 (C 6 H 4 CH=CH 2 ) 2 )] 4- electrostatic interaction Bressanone Sept Hybrid Materials 14 7

8 Bridged Alkoxysilanes () 3 () 3 () 3 -(CH 2 ) n -() 3 () 3 -(CH 2 ) m H C H (CH 2 ) n H (CH 2 ) n C H (CH 2 ) m -() 3 (Et) 3 H S 2 (CH 2 ) 2 H (Et) 3 (Et) 3 H 2+ () 3 H i H 2 H 2 H () 3 Bressanone Sept Hybrid Materials 15 Alkoxysilyl-Substituted rganic Polymers CH 3 (Et) 3 (Et) 3 n CH 3 CH 3 H 2 C n C (Me) 3 (Et) 3 -(CH 2 ) 3 (CH 2 ) 4 - (CH 2 ) 3 -(Et) 3 n Bressanone Sept Hybrid Materials 16 8

9 (ano)particles Pre-formed anostructures Preformed ligomers and Polymers (ano)fibres, anotubes Porous Materials Clays / Layered Materials Bressanone Sept Hybrid Materials 17 Consequences of Introducing rganic Substituents educed degree of crosslinking of the inorganic network Polarity changes (changes in hydrogen bonding) eactivity change of the remaining alkoxide groups (electronic and steric effect of the organic substituents) These effects are an inevitable consequence of the organic modification Bressanone Sept Hybrid Materials 18 9

10 Degree of Crosslinking () 4-n n n = 1-3 () 3 lsesquioxanes Polyhedral ligomeric lsesquioxanes () 2 2 () 3 n ' ligo- and Polysiloxanes Dimers Bressanone Sept Hybrid Materials 19 Influence on eaction ates Example: () 3 () M in methanol, 25 C The dashed line is ph vs. gel time for (Me) 4 (2.0 M in methanol, 60 C). Bressanone Sept Hybrid Materials 20 10

11 Influence on eaction ates (acac = acetylacetonate, ftac =trifluoroacetylacetonate, dbzm = dibenzoylmethanide) Bressanone Sept Hybrid Materials 21 Precursors Molecular precursors Clusters (nano-building blocks, BB) Alkoxysilyl-substituted organic polymers Pre-formed nanostructures Classes of sol-gel hybrid materials Physically entrapped components Functionalized inorganic networks Interpenetrating structures Dual networks Bressanone Sept Hybrid Materials 22 11

12 Types of Inorganic-rganic Hybrid Materials by Sol-Gel Processing Physically entrapped molecules, particles, etc. Interpenetrating inorganic and organic networks Class I materials: weak interactions Class II materials: strong interactions Modification of the gel network by organic groups Dual inorganic and organic networks connected by covalent bonds Bressanone Sept Hybrid Materials 23 Entrapped Biomolecules Bressanone Sept Hybrid Materials 24 12

13 -releasing glucose biosensor (cleaved suppresses degradation by bacteria) Entrapped Biomolecules: Glucose Sensor CH 3 H Glucose oxidase in Me(Et) 3 Gel 2 (CH 2 ) 3 (CH2 ) 6 H H M.H.Schoenfisch et al., 2004 in polyurethan Bressanone Sept Hybrid Materials 25 Entrapped Inorganic Particles: Dental Filling abrasion 9 µm shrinkage 1,97 vol% adhesion 25,8 / 27,6 MPa pyrogenic silica ( 40 nm) + standard dental glass particles ( 0,7 µm) Bressanone Sept Hybrid Materials 26 13

14 Entrapped Inorganic Particles: Controlled elease in 2 Bressanone Sept Hybrid Materials 27 Precursors Molecular precursors Clusters (nano-building blocks, BB) Alkoxysilyl-substituted organic polymers Pre-formed nanostructures Classes of sol-gel hybrid materials Physically entrapped components Functionalized inorganic networks Interpenetrating structures Dual networks Bressanone Sept Hybrid Materials 28 14

15 Heterogenization of Homogeneous Catalysts Classical approach Sol-gel approach A + ML n A ML n A + ML n A ML n A + ML n A + E() n ML n + ML n + ML n A + A A + E() n A Bressanone Sept Hybrid Materials 29 Heterogenization of Catalysts by Sol-Gel Processing A ML n + () 4 Examples: Ph Cl Ph () 3 P h P () 3 Ph C Ph 2 / A ML n Poren pores More active in the hydrosilation of 1-hexene than h(c)cl(p 3 ) 2 U. Schubert et al., 1989 (Et) 3 Ph Cl Ph (Et) 3 P u P P P (Et) 3 Ph Cl Ph (Et) 3 K K sol-gel Sol-Gelprocessing Prozeß K K Synthesis of,-diethylformamide from C 2, H 2 and diethylamine A. Baiker et al., 1999 K K K = katalytisch catalytically aktive active Spezies species K K () 3 H H H Cu Catalyst for the oxidation of 3,5-di-tert.butylcatechol to the quinone M. Louloudi et al., 1998 Bressanone Sept Hybrid Materials 30 15

16 Coatings with ptical Properties Photochromism: fast for optical switches, for eye protection, privacy shields slow for optical data storage, energy conserving coatings, etc... Example: Spirooxazine derivative hν 1 Δ or hν 2 Embedding in sol-gel coatings: For sufficient photochromism: dye concentration > 25 wt% mechanical stability of sol-gel film is deteriorated. Grafting of the dye to the sol-gel matrix higher chromophore concentrations can be achieved without affecting the mechanical integrity of the sol-gel matrix H (Et) 3 Photochromic coating on paper Bressanone Sept Hybrid Materials 31 Precursors Molecular precursors Clusters (nano-building blocks, BB) Alkoxysilyl-substituted organic polymers Pre-formed nanostructures Classes of sol-gel hybrid materials Physically entrapped components Functionalized inorganic networks Interpenetrating structures Dual networks Bressanone Sept Hybrid Materials 32 16

17 Interpenetrating etworks Sequential two-step process: Second network is is formed in in the the first first IP Examples: Generation of the organic polymer in the pores of an inorganic porous material (in channels of zeolites or mesoporous materials, between sheets of a layered lattice, such as a clay mineral) rigid inorganic moiety with a regular pore or channel structure in the nanoscale Inorganic structures form and interpenetrate an organic polymer (difficulties: incompatibility between the moieties phase separation) Bressanone Sept Hybrid Materials 33 Interpenetrating etworks Interaction via hydrogen bonds to silanol groups of the forming silica rganic polymers with hydrogen bonding ability: n n Me 2 H n n n Me n poly(vp) poly(dmaa) poly(va) poly(vac) poly(mma) poly(hema) H () 4 and/or () 3 H 2, [Kat] o macro phase separation esulting materials: high degree of homogeneity and optical transparency Important reaction parameter: ph Change of crosslinking density and interaction with polymer using () 3 /() 4 mixtures Bressanone Sept Hybrid Materials 34 17

18 Interpenetrating etworks + Poly(isopren-block-ethylenoxide) swollen in THF/CH 3 Cl Sol from GLYM and Al( s Bu) 3 (H 2 /HCl) () 3 anostructured hybrid polymer U.Wiesner et al., 2004 Bressanone Sept Hybrid Materials 35 Interpenetrating etworks rganic Monomer Initiator Inorganic Monomer Catalyst Solvent AIB TES H Addition of tetrakis(2-(acryloxy)ethoxy)silane improves homogenity TEM images of the nanocomposites: HF Water C. L. Jackson et al. Chem. Mater. 1996, 8, 727 Increasing Sol-Gel Catalyst Concentration => Faster eaction Bressanone Sept Hybrid Materials 36 18

19 anocomposites: Polymer-Clay Layered solid Layered solid Exfoliated layers + Monomer (Polymerization) + Polymer + Monomer (Polymerization) or + Polymer Bressanone Sept Hybrid Materials 37 anocomposites: Polymer-Clay Bressanone Sept Hybrid Materials 38 19

20 anocomposites: Polymer-Clay 15 μm glass fibre in polyolefin 1 nm thick montmorillonite sheet in epoxy resin Bressanone Sept Hybrid Materials 39 anocomposites: Intercalation of Polymers in Pores + Direct Intercalation Polymer Porous Host Problems: Pore diameter size of Polymer Diffusion of polymer Usually only end of polymer sits in pore but not the whole chain Bressanone Sept Hybrid Materials 40 20

21 anocomposites: Polymerization in Pores + Monomer Intercalation Polymerization Monomer Porous Host Monomer is interacalated into the pores (vapor, liquid), then polymerization T. Aida et al Bressanone Sept Hybrid Materials 41 anocomposites: Polymerization in Pores T. Aida et al T. Bein et al Bressanone Sept Hybrid Materials 42 21

22 Precursors Molecular precursors Clusters (nano-building blocks, BB) Alkoxysilyl-substituted organic polymers Pre-formed nanostructures Classes of sol-gel hybrid materials Physically entrapped components Functionalized inorganic networks Interpenetrating structures Dual networks Bressanone Sept Hybrid Materials 43 Preparation strategies Dual etwork Structures Concomitant formation of the inorganic and organic structures Stepwise formation of the organic and inorganic networks from pre-formed organic structures from pre-formed inorganic structures ptions Chemical composition of the inorganic component(s) Chemical composition of the organic component(s) Proportion of the inorganic/organic components Curing method (thermal / photochemical) Dimension of the inorganic / organic components (molecular, nanometer, extended) Bressanone Sept Hybrid Materials 44 22

23 Concomitant Formation of Inorganic and rganic etwork Typical procedure Hydrolysis Condensation Precursors Metal Alkoxides Metal Salts + water (ev. catalyst or additives) - alcohol Sol Gelation formation of inorganic network Gel Hardening (thermal or uv) Hybrid Polymer formation of organic network Many Examples: Coatings Section Bressanone Sept Hybrid Materials 45 Concomitant Formation of Inorganic and rganic etwork ften used precursors () 3 () 3 H () 3 or + Zr() 4 + () 4, Zr() 4, Al() 3, etc. increase of inorganic / organic ratio + acrylate, epoxide monomers, etc. decrease of inorganic / organic ratio Bressanone Sept Hybrid Materials 46 23

24 Concomitant Formation of Inorganic and rganic etwork Sequential formation of the organic network photo-initiator, hν UV-polymerization of methacryl groups ΔT thermal polymerization of epoxy groups Bressanone Sept Hybrid Materials 47 *) SBU: Sequentially Built-up Concomitant Formation of Inorganic and rganic etwork H 2 / af 2 + aq. MP CH 2 4 CH 2 H n (CH 2 ) 2 4 H 2 / af Free adical Polymerization 2 + (CH 2 ) 2 H 4 Bressanone Sept Hybrid Materials 48 24

25 Photochemical Crosslinking (3D Laser Lithography) Coating or forming of MCE (with chromophor as UV initiator) Direct 3D-laser writing (2-photon polymerisation with femtosecond laser pulses) Development of the structure (removal of uncured MCE ) equirements for hardening: precise focussing 2-photon process polymerisation in rmocer layer ( 2 protection) chromophor as initiator rmocer = rganically modified Ceramics Bressanone Sept Hybrid Materials 49 Photochemical Crosslinking (3D Laser Lithography) CAD File Layer model Venus of Milo in MCE (EM) I am made from MCE! Bressanone Sept Hybrid Materials 50 25

26 Photochemical Crosslinking (3D Laser Lithography) Bressanone Sept Hybrid Materials 51 Hybrid Polymers from Pre-Formed rganic Polymers Low shrinkage by the use of prepolymerized materials CH 3 CH 3 x y acrylic component silane component (Me) 3 (H 2 C) 3 Me 1. inorganic condensation 2. organic polymerization acrylic monomer + polymer (incomplete polymerization) inorganic condensation between fully polymerized polyacrylate Bressanone Sept Hybrid Materials 52 26

27 Hybrid Polymers from Pre-Formed rganic Polymers Hybrid Materials applying Dendrimers Porous Materials using Dendrimers as Templates A.-M. Caminade, J.-P. Majoral, J. Mater. Chem., 2005, 15, Bressanone Sept Hybrid Materials 53 Hybrid Polymers from Pre-Formed Inorganic Structures Bressanone Sept Hybrid Materials 54 27

28 Hybrid Polymers from Pre-Formed Inorganic Structures Improved Properties through Controlled einforcement of Polymer Chains at the Molecular Level ' Property enhancements via PSS observed in PSS-copolymers and blends Increased T dec Increased T g educed Flammability educed Heat Evolution Lower Density Disposal as lica Extended Temperature ange Increased xygen Permeability Lower Thermal Conductivity Thermoplastic or Curable Enhanced Blend Miscibility xidation esistance Altered Mechanicals educed Viscosity Bressanone Sept Hybrid Materials 55 Hybrid Polymers from Pre-Formed Inorganic Structures PSS for fire retardant materials Bressanone Sept Hybrid Materials 56 28

29 Hybrid Polymers from Pre-Formed Inorganic Structures Polymerizable Metal xo Clusters X X X X X X X X X Polymerizable groups X Zr 6 4 (H) 4 (methacrylate) 12 for free radical polymerization Zr 6 4 (H) 4 (5-norbornene-2-carboxylate) 12 for MP Bressanone Sept Hybrid Materials 57 Hybrid Polymers from Pre-Formed Inorganic Structures Metal xo Clusters as Initiators for ATP multifunctional initiator + monomer + catalyst + solvent X X X X X X X X X = PMMA, PS, P t BuA catalyst = pmdeta / CuBr or CuCl e.g. Ti 6 4 (CCBrMe 2 )( i Pr) 8 G.Kickelbick et al. Bressanone Sept Hybrid Materials 58 ln (M 0 /M) Polydispersities < % of the chain ends still active after isolation ln (M 0 /M) linear Fit for ln (M 0 /M) Y=0,0058*X =0, Time [min] Conversion [%] 29

30 Hybrid Polymers from Pre-Formed Inorganic Structures Combination of polyoxometallates (electrochromism, photochromism, conductivity, redox activitities) + conjugated molecules and polymers electrically active organic materials (light emitting diodes, field-effect transistors, solid-state lasers) Monofunctionalization of Mo Examples: Z. Peng et al Bressanone Sept Hybrid Materials 59 Hybrid Polymers from Pre-Formed Inorganic Structures Z. Peng et al Bressanone Sept Hybrid Materials 60 30

31 Hybrid Polymers from Pre-Formed Inorganic Structures Magnetic Polymers Mn (C-CH=CH 2 ) 16 adical polymerization + CH 2 =CMe-CMe PMMA crosslinked by Mn 12 Mn 12 total cluster spin S = 10 (4 Mn IV, S = 3 / Mn III, S = 2) Superparamagnetic Bressanone Sept Hybrid Materials 61 Hybrid Polymers from Pre-Formed Inorganic Structures Preparation of nanoparticles Surface modification (Et) 3 (H 2 C) 3 Stöber-Process Initiators at the surface, e.g. C CH 3 CH 3 CH 3 C (Et) 3 (H 2 C) 3 (Et) 4 + H 4 H FG FG FG FG FG 2 FG CH 3 Br FG CH 3 FG () 3 H H H H H H 2 H H H H H H FG H H H H H H H H H H Polymerization from the functionalised surface G.Kickelbick et al. AFM Bressanone Sept Hybrid Materials 62 31

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