Diels-Alder Click-Crosslinked Hydrogels with Increased Reactivity Enable 3D Cell
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1 Diels-Alder Click-Crosslinked Hydrogels with Increased Reactivity Enable 3D Cell Encapsulation Supporting Information Figure S1: Characteristic rheological time sweep for HAmF Hydrogel O O O N O O O N -OH O N - O OH O O HN OH Figure S2: Mechanism of maleimide hydrolysis
2 Figure S3 M06-2x/6-311+G** calculated donor-acceptor interaction and calculated topological properties by QTAIM. The key CH methyl O interaction discussed is highlighted. Figure S4: Zoomed in section of furanic peaks of 1 H NMR spectrum of unreacted HAmF (top) and hyaluronidase-digested HA-mF/PEG hydrogels (bottom) Selected DFT Calculated Transition state geometries, pre-complexes, products and the related reactants & Thermochemical Data for Diels-Alder reaction of Furan-modified Hyaluronan (HA-FA) and methyl Furan-modified Hyaluronan (HA-mF) with maleimide Furan-modified Hyaluronan (HA-FA)
3 # opt=calcfc freq=noraman rb3lyp/6-31g(d,p) scrf=(iefpcm,solvent=water) geom=connectivity temperature=311 Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= C C O C C C C O O N C O O C H H H H H H
4 H H H H H H H O C C C O H C O H C C O H O H O H H H C H H H C H H H N H C H H C C C H C H O
5 H methyl Furan-modified Hyaluronan (HA-mF) # opt=calcfc freq=noraman b3lyp/6-31g(d,p) scrf=(iefpcm,solvent=water) geom=connectivity temperature=311 Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= C C O C C C C O O N C O O C H
6 H H H H H H H H H H H H O C C C O H C O H C C O H O H O H H H C H H H C H H H N H C H H C C
7 C H C H O C H H H Truncated maleimide # opt=calcfc freq=noraman b3lyp/6-31g(d,p) scrf=(iefpcm,solvent=water) geom=connectivity temperature=311 Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= C C C C H H O O N
8 C C H H H H O C H H H Pre-complex of DA reaction between HA-FA and maleimide (Endo route) # opt=calcfc freq=noraman b3lyp/6-31g(d,p) scrf=(iefpcm,solvent=water) geom=connectivity temperature=311 Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= SCF (RM062X/ g(d,p)) = C C O C C
9 C C O O N C O O C H H H H H H H H H H H H H O C C C O H C O H C C O H O H O H H H C H H H C
10 H H H N H C H H C C C H C H O C C C C H H O O N C C H H H H H O C H H H Transition state of DA reaction between HA-FA and maleimide (Endo route)
11 # opt=(calcfc,ts,noeigen) freq=noraman b3lyp/6-31g(d,p) scrf=(iefpcm,solvent=water) geom=connectivity temperature=311 Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= SCF (RM062X/ g(d,p)) = C C O C C C C O O N C O O C H H H H H
12 H H H H H H H H O C C C O H C O H C C O H O H O H H H C H H H C H H H N H C H H C C C H C H
13 O C C C C H H O O N C C H H H H H O C H H H Product of DA reaction between HA-FA and maleimide (Endo route) # opt=calcfc freq=noraman b3lyp/6-31g(d,p) scrf=(iefpcm,solvent=water) geom=connectivity temperature=311 Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy=
14 Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= SCF (RM062X/ g(d,p)) = C C O C C C C O O N C O O C H H H H H H H H H H H H H O C C C O H C O H C C
15 O H O H O H H H C H H H C H H H N H C H H C C C H C H O C C C C H H O O N C C H H H H H O C
16 H H H Pre-complex of DA reaction between HA-FA and maleimide (Exo route) # opt=calcfc freq=noraman b3lyp/6-31g(d,p) scrf=(iefpcm,solvent=water) geom=connectivity temperature=311 Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= SCF (RM062X/ g(d,p)) = C C O C C C C O O N C O O C
17 H H H H H H H H H H H H H O C C C O H C O H C C O H O H O H H H C H H H C H H H N H C H H C
18 C C H C H O C C N C C O O H H C C H H H H H O C H H H Transition state of DA reaction between HA-FA and maleimide (Exo route)
19 # opt=(calcfc,ts,noeigen) freq=noraman b3lyp/6-31g(d,p) scrf=(iefpcm,solvent=water) geom=connectivity temperature=311 Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= SCF (RM062X/ g(d,p)) = C C O C C C C O O N C O O C H H H H H H H H H H H H H O C C C O H
20 C O H C C O H O H O H H H C H H H C H H H N H C H H C C C H C H O C C N C C O O H H C C H H
21 H H H O C H H H Product of DA reaction between HA-FA and maleimide (Exo route) # opt=calcfc freq=noraman b3lyp/6-31g(d,p) scrf=(iefpcm,solvent=water) geom=connectivity temperature=311 Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= SCF (RM062X/ g(d,p)) = C C O C C C
22 C O O N C O O C H H H H H H H H H H H H H O C C C O H C O H C C O H O H O H H H C H H H C H
23 H H N H C H H C C C H C H O C C N C C O O H H C C H H H H H O C H H H Pre-complex of DA reaction between HA-mF and maleimide (Endo route)
24 # opt=calcfc freq=noraman b3lyp/6-31g(d,p) scrf=(iefpcm,solvent=water) geom=connectivity temperature=311 Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= SCF (RM062X/ g(d,p)) = C C O C C C C O O N C O O C H H H H H H H H
25 H H H H H O C C C O H C O H C C O H O H O H H H C H H H C H H H N H C H H C C C H C H O C H
26 H H C C C C H H O O N C C H H H H O C H H H Transition state of DA reaction between HA-mF and maleimide (Endo route) # opt=(calcfc,ts,noeigen) freq=noraman b3lyp/6-31g(d,p) scrf=(iefpcm,solvent=water) geom=connectivity temperature=311 Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy=
27 Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= SCF (RM062X/ g(d,p)) = C C O C C C C O O N C O O C H H H H H H H H H H H H H O C C C O H C O H C C O
28 H O H O H H H C H H H C H H H N H C H H C C C H C H O C H H H C C C C H H O O N C C H H H H
29 O C H H H Product of DA reaction between HA-mF and maleimide (Endo route) # opt=calcfc freq=noraman b3lyp/6-31g(d,p) scrf=(iefpcm,solvent=water) geom=connectivity temperature=311 Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= SCF (RM062X/ g(d,p)) = C C O C C C C O
30 O N C O O C H H H H H H H H H H H H H O C C C O H C O H C C O H O H O H H H C H H H C H H H
31 N H C H H C C C H C H O C H H H C C C C H H O O N C C H H H H O C H H H Pre-complex of DA reaction between HA-mF and maleimide (Exo route)
32 # opt=calcfc freq=noraman b3lyp/6-31g(d,p) scrf=(iefpcm,solvent=water) geom=connectivity temperature=311 Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= SCF (RM062X/ g(d,p)) = C C O C C C C O O N C O O C H H H H H
33 H H H H H H H H O C C C O H C O H C C O H O H O H H H C H H H C H H H N H C H H C C C H C H
34 O C H H H C C N C C O O H H C C H H H H O C H H H Transition state of DA reaction between HA-mF and maleimide (Exo route)
35 # opt=(calcfc,ts,noeigen) freq=noraman b3lyp/6-31g(d,p) scrf=(iefpcm,solvent=water) geom=connectivity temperature=311 Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= SCF (RM062X/ g(d,p)) = C C O C C C C O O N C O O C H H H H H H H H H H H H H O C C C O
36 H C O H C C O H O H O H H H C H H H C H H H N H C H H C C C H C H O C H H H C C N C C O O H
37 H C C H H H H O C H H H Product of DA reaction between HA-mF and maleimide (Exo route) # opt=calcfc freq=noraman b3lyp/6-31g(d,p) scrf=(iefpcm,solvent=water) geom=connectivity temperature=311 Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= SCF (RM062X/ g(d,p)) = C C O
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