Structure–Activity Relationships of Voltaglue Organic Blends

Tan, Nigel Chew Shun; Ghosh, Animesh; Steele, Terry W. J.

doi:10.1002/marc.202000188

Cited by 5 publications

(2 citation statements)

References 20 publications

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“…Diazirine offers many methods of activation, including light exposure (photocuring), heating above 80 °C (thermal curing), or voltage (electrocuring). Depending on the activation stimuli, metastable intermediates are formed capable of covalently crosslinking all amino acids [22,24–27] . The electrochemical curing mechanism possesses inherent advantages over heat and light: 1) substrates can be opaque; 2) it avoids temperatures (>60 °C) that denature proteins or exceeds the Tg/Tc of labile biomaterials; 3) it can be precisely controlled externally via microcontrollers.…”

Section: Introductionmentioning

confidence: 99%

Precise Control of Diazirine Reduction to Tune the Mechanical Properties of Electrocuring Adhesives

et al. 2021

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There is a growing interest in developing innovative adhesive materials that offer stimuli-responsive mechanical properties. Electrocuring adhesives exploit electric-field stimuli towards initiating and propagating polymerization reactions with projected benefits of on-demand adhesion and microelectronic control. Voltaglue is a recently developed biocompatible, waterbased bioadhesive that combines a biomacromolecule (polyamidoamine, PAMAM) with a grafted electrochemical crosslinker (diazirine) where the former mediates viscoelastic properties and the latter voltage-based activation. Through this relatively simple design, a range of viscoelastic and adhesive properties are possible by controlling the intensity (voltage) and duration (coulombs) of the electric field. For the first time, bioadhesive properties are correlated to the moles of diazirine reduced during electrocuring via chronoamperograms. The method is based on the precise measurement of the charge exchanged during the reductive reaction which ultimately results in a series of voltage/time combinations that can be used to drive diazirine activation and charge quantitation. A strong correlation is finally observed between diazirine electrolysis and specific mechanical properties of the cured adhesive. This ultimately enables fine-tune control over the adhesive properties with benefits in a wide variety of applications ranging from electromagnetic biomaterials to additive manufacturing.

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Section: Introductionmentioning

confidence: 99%

Precise Control of Diazirine Reduction to Tune the Mechanical Properties of Electrocuring Adhesives

et al. 2021

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“…In a two‐part adhesive formulation with epoxy resins, PAMAM dendrimers allow rapid gelation and strong bonding, [9,10] although they suffers from limited manipulation. On the other hand, PAMAM derived one‐pot adhesives suffer from weak adhesion strength [11–13] . It is hypothesized that aryl sulfonyl functionalized PAMAM should be stable in presence of an epoxy resin and therefore, can be used to formulate one‐pot structural or bioadhesives.…”

Section: Introductionmentioning

confidence: 99%

Optimizing the Reduction Potential of Sulfonamides on Polyamidoamine Dendrimers

et al. 2020

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Abstractp‐Toluenesulfonamide serves as an important functional group to protect alkyl amines. However, the electrochemical deprotection of sulfonamides requires relatively high reduction potentials (−2.4 V vs SCE) that would interfere with other functional groups. Previous investigations suggest that methods are available to decrease the reduction potential, but no systematic investigation has been conducted that evaluates the reduction potential as a function of aryl‐substitution, mediator, or multi‐arm grafting. Cyclic voltammetric studies of a library of bis‐sulfonamides bearing different aryl substituents in DMF reveals that p‐NO2 substituted bis‐sulfonamide has the lowest reduction potential. Further investigations aimed at lowering the cathodic potential with polycyclic aromatic hydrocarbon mediators display negligible or no impact. This optimized condition was successfully applied to fully p‐nitrobenzenesulfonyl protected generation‐zero and generation‐one polyamidoamine dendrimers (G0.0‐PAMAM‐Ns and G1.0‐PAMAM‐Ns, respectively), demonstrating successful amine protection and deprotection on dendrimers for the first time.

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