Tuning conductivity while maintaining mechanical properties in perylene bisimide hydrogels at physiological pH

Jimenez, Juan Antonio Mena; Egan, Jacquelyn; Randle, Rebecca I.; Rezig, Amina Omelbanine; Orimolade, Benjamin O.; Ginesi, Rebecca E.; Schweins, Ralf; Riehle, Mathis O.; Draper, Emily R.

doi:10.1039/d3cc04557a

Chem. Commun.

2024

DOI: 10.1039/d3cc04557a

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Tuning conductivity while maintaining mechanical properties in perylene bisimide hydrogels at physiological pH

Juan Antonio Mena Jimenez,

Jacquelyn Egan,

Rebecca I. Randle

et al.

Abstract: Using different salts as a method of gelation of two different amino acid functionalised perylene bisimides we are able to tune the reduction potentials, whilst mainatining the mechanical and optical...

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Cited by 4 publications

References 26 publications

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3D‐Printing Multi‐Component Multi‐Domain Supramolecular Gels with Differential Conductivity

Vadukoote,

Avestro,

Smith

2024

Angewandte Chemie

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We report the use of wet‐spinning to 3D‐print gels from low‐molecular‐weight gelators (LMWGs) based on the 1,3:2,4‐dibenzylidenesorbitol (DBS) scaffold. Gel stripes assembled from DBS‐CONHNH2 and DBS‐COOH are printed, and their conductivities assessed. Printed gels based on DBS‐CONHNH2 can be loaded with Au(III), which is reduced in situ to form embedded gold nanoparticles (AuNPs). The conductivity of these gels increases because of electron transport mediated by the AuNPs, whereas the conductivity of DBS‐COOH, which does not promote AuNP formation, remains lower. We then fabricate multi‐component gel patterns comprised of spatially well‐defined domains of printed DBS‐CONHNH2/AuNP (higher conductivity) and DBS‐COOH (lower conductivity) resulting in soft multi‐domain materials with differential conductivity. Such materials have future prospects in applications such as soft nanoelectronics or tissue engineering.

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3D‐Printing Multi‐Component Multi‐Domain Supramolecular Gels with Differential Conductivity

Vadukoote,

Avestro,

Smith

2024

Angewandte Chemie

View full text Add to dashboard Cite

show abstract

3D‐Printing Multi‐Component Multi‐Domain Supramolecular Gels with Differential Conductivity

Vadukoote,

Avestro,

Smith

2024

Angew Chem Int Ed

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Boosting Supramolecular Gelation Efficiency and Properties: Ionic Strength as a Key to Superior Hydrogels

Duraisamy,

Chellani,

Saveri

et al. 2024

Langmuir

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Controlling the minimum gelation concentration (MGC) of low molecular weight (LMW) hydrogelators is a key for modulating gel properties, such as mechanical strength, viscoelasticity, and stability, which are crucial for applications ranging from drug delivery to tissue engineering. However, tweaking the MGC under specific conditions, such as pH and/or temperature, poses a considerable challenge. Herein, we varied the ionic strength of buffer solutions using NaCl for several LMW hydrogelators, including Fmoc-Phe, Fmoc-Tyr, Fmoc-Trp, Fmoc-Met, and Fmoc-Cha, and assessed their gelation efficiency at pH 7.4 and ambient temperature. Interestingly, Fmoc-Phe demonstrated a ∼67% (3fold) MGC reduction, from 0.24 to 0.08 wt %, at 500 mM NaCl, transforming it a "super hydrogelator" (MGC < 0.1 wt %), while Fmoc-Trp showed 60% MGC reduction. Higher ionic strength effectively shields the electrostatic repulsion between negatively charged (−COO − ) groups on the Fmoc-Phe, promoting closer aggregation and more efficient self-assembly and allowing for gelation at lower concentrations. In contrast, Fmoc-Met, Fmoc-Cha, and Fmoc-Tyr precipitated in the presence of NaCl, suggesting that NaCl specifically modulates the MGC of Fmoc-amino acid gelators containing unsubstituted aromatic side chains. Furthermore, these results indicate that cation-π interactions likely play a role, alongside carboxylic acid neutralization. While Fmoc-Phe forms gels in the presence of other monovalent cations, it does not form a hydrogel in the presence of divalent (CaCl 2 ) and trivalent (AlCl 3 ), indicating that enhancement of hydrogelation is specific to monovalent cations. Although the fibrillar structure of Fmoc-Phe hydrogels remained consistent, addition of NaCl increased fibril stickiness, creating densely packed networks that modulate the mechanical strength. Unlike typical cases where increased ionic strength leads to precipitation, Fmoc-Phe gelation at high NaCl concentrations (150−500 mM) is significant, yielding a robust supramolecular hydrogel that remains stable in high ionic-strength environments. This outcome suggests that ionic strength could be a valuable factor to enhance the efficient gelation of LMW hydrogelators.

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Tuning conductivity while maintaining mechanical properties in perylene bisimide hydrogels at physiological pH

Abstract: Using different salts as a method of gelation of two different amino acid functionalised perylene bisimides we are able to tune the reduction potentials, whilst mainatining the mechanical and optical...

Cited by 4 publications

References 26 publications

3D‐Printing Multi‐Component Multi‐Domain Supramolecular Gels with Differential Conductivity

3D‐Printing Multi‐Component Multi‐Domain Supramolecular Gels with Differential Conductivity

3D‐Printing Multi‐Component Multi‐Domain Supramolecular Gels with Differential Conductivity

Boosting Supramolecular Gelation Efficiency and Properties: Ionic Strength as a Key to Superior Hydrogels

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