Aryldiazonium salt derived mixed organic layers: From surface chemistry to their applications

Jiang, Cheng; Silva, Saimon Moraes; Fan, Sanjun; Wu, Yanfang; Alam, Muhammad Tanzirul; Liu, Guozhen; Gooding, J. Justin

doi:10.1016/j.jelechem.2016.11.043

Cited by 68 publications

(58 citation statements)

References 129 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The blocking effect of the aryl layers was assessed using Fe(CN) 6 3−/4− , as depicted in Figure 2. The quasi-reversible redox wave obtained with bare ITO (Figure 2A (Figure 2A(c)), indicating a blocking effect of the aryl layer as reported by several authors [22,[42][43][44][45][46][47]. The relative Fe(CN) 6 3−/4− redox peak intensity (I rel ) decreased in the order ITO > ITO-N(CH 3 ) 2 > ITO-NH 2 > ITO-NH-Ph > ITO-CN > ITO-CO 2 H > ITO-SO 3 H (see Table 1).…”

Section: Electrochemical Modification Of Flexible Ito Sheets With Diasupporting

confidence: 81%

Diazonium Salts: Versatile Molecular Glues for Sticking Conductive Polymers to Flexible Electrodes

Pires

Diaw

et al. 2018

Surfaces

View full text Add to dashboard Cite

Adhesion of polymers to surfaces is of the upmost importance in timely applications such as protective coatings, biomaterials, sensors, new power sources and soft electronics. In this context, this work examines the role of molecular interactions in the adhesion of polypyrrole thin films to flexible Indium Tin Oxide (ITO) electrodes grafted with aryl layers from various diazonium salts, namely 4-carboxybenzenediazonium (ITO-CO2H), 4-sulfonicbenzenediazonium (ITO-SO3H), 4-N,N-dimethylbenzenediazonium (ITO-N(CH3)2), 4-aminobenzenediazonium (ITO-NH2), 4-cyanobenzenediazonium (ITO-CN) and 4-N-phenylbenzenediazonium (ITO-NHPh). It was demonstrated that PPy thin layers were adherent to all aryl-modified surfaces, whereas adhesive failure was noted for bare ITO following simple solvent washing or sonication. Adhesion of polypyrrole was investigated in terms of hydrophilic/hydrophobic character of the underlying aryl layer as probed by contact angle measurements. It was found that sulfonic acid-doped polypyrrole (PPy-BSA) thin films were preferably deposited on the most hydrophobic surfaces. More importantly, the redox properties and electrochemical impedance of PPy were closely related to the hydrophobic character of the aryl layers. This work demonstrates that diazonium compounds are unique molecular glues for conductive polymers and permit to tune their interfacial properties. With robust, diazonium-based architectured interfaces, one can design high performance materials for e.g., sensors, printed soft electronics and flexible thermoelectrics.

show abstract

Section: Electrochemical Modification Of Flexible Ito Sheets With Diasupporting

confidence: 81%

Diazonium Salts: Versatile Molecular Glues for Sticking Conductive Polymers to Flexible Electrodes

Pires

Diaw

et al. 2018

Surfaces

View full text Add to dashboard Cite

show abstract

“…39,41 Furthermore, because the grafting of these calix [4]arenes via C-Au bonds is irreversible, homogeneous mixtures of calixarenes can be grafted. 42 On gold surfaces, the ratio between two different calixarenes grafted on the surface reflects the one in the solution. 43 Additionally, the use of calix [4]arenes with carboxylates allows the post-functionalisation of the surfaces to which it is grafted.…”

Section: Introductionmentioning

confidence: 99%

Controlled Functionalization of Gold Nanoparticles with Mixtures of Calix[4]arenes Revealed by Infrared Spectroscopy

Valkenier¹,

Malytskyi²,

Blond³

et al. 2017

Langmuir

View full text Add to dashboard Cite

Labile ligands such as thiols and carboxylates are commonly used to functionalize AuNPs, though little control over the composition is possible when mixtures of ligands are used. It was shown recently that robustly functionalized AuNPs can be obtained through the reductive grafting of calix[4]arenes bearing diazonium groups on the large rim. Here, we report a calix[4]arene-tetradiazonium decorated by four oligo(ethylene glycol) chains on the small rim, which upon grafting gave AuNPs with excellent stability thanks to the C-Au bonds. Mixtures of this calixarene and one with four carboxylate groups were grafted on AuNPs. The resulting particles were analyzed by infrared spectroscopy, which revealed that the composition of the ligand shell clearly reflected the ratio of calixarenes that was present in solution. This strategy opens the way to robustly protected AuNPs with well-defined numbers of functional or postfunctionalizable groups.

show abstract

“…[22,41] The blocking effect of the aryl layers was assessed using Fe(CN)6 3-/4-, as depicted in noted by several authors. [22,42,43,44,45,46,47] The relative Fe(CN)6 3-/4-redox peak intensity (Irel) decreased in the order ITO>ITO-N(CH3)2> ITO-NH2>ITO-NH-Ph>ITO-CN>ITO-CO2 H>ITO-SO3H (see Table 1).…”

Section: Electrochemical Modification Of Flexible Ito Sheets With Diamentioning

confidence: 97%

Diazonium Salts: Versatile Molecular Glues for Sticking Conductive Polymers to Flexible Electrodes

Lo¹,

Pires²,

Diaw³

et al. 2018

Preprint

View full text Add to dashboard Cite

Adhesion of polymers to surfaces is of upmost importance in timely applications such as protective coatings, biomaterials, sensors, new power sources and soft electronics. In this context, this work examines the role of molecular interactions in the adhesion of polypyrrole thin films to flexible Indium Tin Oxide (ITO) electrodes grafted with aryl layers from various diazonium salts, namely 4-carboxybenzenediazonium (ITO-CO2H), 4-sulfonicbenzenediazonium (ITO-SO3H), 4-N,N dimethylbenzenediazonium (ITO-N(CH3)2), 4-aminobenzenediazonium (ITO-NH2), 4-cyanobenzenediazonium (ITO-CN) and 4-N-phenylbenzenediazonium (ITO-NHPh). It was demonstrated that PPy thin layers were adherent to these surfaces, whereas adhesion failure was noted on bare ITO, following simple solvent washing or sonication. Adhesion of the polypyrrole was investigated in terms of the hydrophilic/hydrophobic character of the underlying aryl layer as probed by contact angle measurements. It was found that sulfonic acid doped polypyrrole (PPy-BSA) thin films were preferably deposited on the most hydrophobic surfaces. More importantly, the redox properties and electrochemical impedance of PPy were closely related to the hydrophobic character of the aryl layers. This work demonstrates that diazonium compounds are unique molecular glues for conductive polymers, and permit to tune their interfacial properties. With diazonium-based robust, architectured interfaces, one can design high performance materials for e.g.sensors, printed soft electronics and flexible thermoelectrics.

show abstract

Aryldiazonium salt derived mixed organic layers: From surface chemistry to their applications

Cited by 68 publications

References 129 publications

Diazonium Salts: Versatile Molecular Glues for Sticking Conductive Polymers to Flexible Electrodes

Diazonium Salts: Versatile Molecular Glues for Sticking Conductive Polymers to Flexible Electrodes

Controlled Functionalization of Gold Nanoparticles with Mixtures of Calix[4]arenes Revealed by Infrared Spectroscopy

Diazonium Salts: Versatile Molecular Glues for Sticking Conductive Polymers to Flexible Electrodes

Contact Info

Product

Resources

About