Functionalization of conducting polymers for biointerface applications

Hackett, Alissa J.; Malmström, Jenny; Travaš-Sejdić, Jadranka

doi:10.1016/j.progpolymsci.2017.03.004

Cited by 94 publications

(87 citation statements)

References 140 publications

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“…It should be noted, however, that despite the higher initiator density on the macroinitiator, the incorporation of PeesBro in a CP matrix will decrease the actual density of grafting sites on the surfaces. For many of the applications of conducting polymers, a tool to alter the surface chemistry of the conductive substrate is very important regardless of whether the grafting to do so can achieve densely grafted true polymer brushes or not . Grafting efficiency from PeesBro with an approximate DP of 25, as described here, may also be compromised by the dopant leaching out of the CP film – especially when incorporated in more hydrophilic CPs which may swell during grafting in aqueous solution.…”

Section: Resultsmentioning

confidence: 99%

“…On PeesBro itself, the initiating site density is high enough to be well within the brush regime, however. For conducting polymers though, where many are challenging to functionalise without losing conductivity, there is a real benefit of being able to incorporate a handle to graft from to change overall film characteristics and wettability – regardless of whether true polymer brushes are produced or not …”

Section: Resultsmentioning

confidence: 99%

“…A flexible approach for the synthesis of CP‐based molecular brushes with surface‐confined backbones is to electropolymerise a CP ‘macroinitiator’ for controlled radical polymerisation (CRP) from monomers incorporating a reversible addition–fragmentation chain transfer agent or atom transfer radical polymerisation (ATRP)‐initiating site . Surface‐initiated CRP techniques allow for growth of polymer brushes with low polydispersity, can provide control over the molecular weight of grafted side chains, and give access to grafting of a wide range of monomers with desirable chemical functionalities …”

Section: Introductionmentioning

confidence: 99%

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Dopant macroinitiator for electropolymerisation and functionalisation of conducting polymer thin films

et al. 2017

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Grafting of polymer brushes from conducting polymer (CP) thin films by controlled radical polymerisation provides a versatile route for the synthesis of functional, electroactive surfaces, with applications in diverse fields. However, one of the drawbacks of this approach is the difficulty of upscaling the synthesis due to the need for specialised CP precursor monomers functionalised with initiation sites. We herein describe an alternative approach to the synthesis of CP-based polymer brushes whereby atom transfer radical polymerisation initiation sites are attached to a macrodopant incorporated into CP films during electropolymerisation. The facile electropolymerisation of commonly studied CPs with an initiator-functionalised macrodopant -poly[(styrene sulfonate)-co-(2-bromopropionyloxyethyl methacrylate)] -is demonstrated. The composite polymer films thus synthesised were used as substrates for grafting of hydrophilic polymer brushes. Although poly(styrene sulfonate) is commonly used as a macrodopant in CP films, its initiator-functionalised derivatives have not previously been utilised in this manner. Despite the elegance of this approach, to the authors' knowledge, there have been no previous examples reported of utilising macromolecular dopants as initiators for subsequent grafting of polymer brushes.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Dopant macroinitiator for electropolymerisation and functionalisation of conducting polymer thin films

et al. 2017

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“…The next generation of bioelectronics will require materials with tunable functionality that specifically addresses the requirements for an application, such as modulating mechanical softness for tissue engineering or providing a mixture of ionic and electronic conductivity for biosensing applications . Organic electronic materials, notably conjugated polymers (CPs), offer many advantageous properties for bioelectronics; the most valuable being both ionic and electrical conductivity (when doped), ease of chemical functionalization, and solution processability through the addition of side chains . For instance, side chain engineering of CPs has rendered the material's solubility to facilitate large‐area fabrication of organic devices and sensors through solution‐based processes .…”

mentioning

confidence: 99%

“…Our PPyP backbone contained i) a methoxy side chain (temonomer 1 ), ii) an azide moiety ( 2 ), and iii) an initiating site for ATRP ( 3 ). Termonomer 1 served as spacer unit with the purpose of controlling the grafting density of the resulting graft copolymers, while termonomers 2 and 3 allowed for functionalization of PPyP by azide–alkyne “click” reactions and grafting of low dispersity polymeric side chains, respectively. Initially, polymeric brushes were grafted onto termonomer 3 by means of ATRP to provide solubility for the resulting PPyP .…”

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confidence: 99%

Molecular “Building Block” and “Side Chain Engineering”: Approach to Synthesis of Multifunctional and Soluble Poly(pyrrole phenylene)s

Chan

Baek

Tan

et al. 2018

Macromol. Rapid Commun.

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Here, the synthesis of a novel poly(pyrrole phenylene) (PpyP) that is both modular in ways of functionalization and soluble in organic solvents is reported, and therefore solution processable. This is achieved through the functionalization of the side‐chain substituents in pyrrole phenylene (PyP) repeating units. t Butyl acrylate brushes are first grafted through atom transfer radical polymerization from one type of PyP, followed by oxidative chemical co‐polymerization of the grafted PyP with a PyP bearing different side chains—either an azide or a methoxy moiety, resulting in a soluble PpyP where solubility is not dopant‐dependent. Successful post‐polymerization modification through “click” chemistry and post‐polymerization processing via electrospinning are also demonstrated. Additionally, performed computational calculations indicate planarity of the novel polyrrole phenylene monomers and ionisation potentials that favor α–α bond formation during their polymerization.

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Dynamic Poly(3,4‐ethylenedioxythiophene)s Integrate Low Impedance with Redox‐Switchable Biofunction

Lin

Zhu

et al. 2018

Adv Funct Materials

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To generate the electrical communication, biocompatibility, and controlled cell attachment properties required for advanced bioelectronic technologies, a dynamic poly(3,4‐ethylenedioxythiophene) (PEDOT) film is developed based on a biomimetic approach. The dynamic PEDOT integrates low impedance, nonspecific‐binding resistance, and redox‐responsive characteristics while coupling with cells stably and specifically. The combination of these features ensures stable and efficient electrical communication with cells and promises potentially reduced disruption of complexes in physiological environments due to the material's strong resistance to nonspecific interactions; more significantly, the integration of these features in one material enables the spatiotemporal attachment and detachment of cells on demand without damage to cell viability and neurites after 5 d of electrical stimulation and culturing. The dynamic and biomimetic PEDOT material can be an ideal electronic interface with optimized electrochemical and biological characteristics toward biocompatible and controllable electrocoupling with cells at low impedance.

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Functionalization of conducting polymers for biointerface applications

Cited by 94 publications

References 140 publications

Dopant macroinitiator for electropolymerisation and functionalisation of conducting polymer thin films

Dopant macroinitiator for electropolymerisation and functionalisation of conducting polymer thin films

Molecular “Building Block” and “Side Chain Engineering”: Approach to Synthesis of Multifunctional and Soluble Poly(pyrrole phenylene)s

Dynamic Poly(3,4‐ethylenedioxythiophene)s Integrate Low Impedance with Redox‐Switchable Biofunction

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