Fluorogenic Gold Nanoparticle (AuNP) Substrate: A Model for the Controlled Release of Molecules from AuNP Nanocarriers via Interfacial Staudinger–Bertozzi Ligation

Luo, Wilson; Gobbo, Pierangelo; Gunawardene, Praveen; Workentin, Mark S.

doi:10.1021/acs.langmuir.6b03647

Cited by 16 publications

(23 citation statements)

References 29 publications

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“…As a result of these qualities, SPAAC has been extensively used in chemical biology, − as it is bioorthogonal and facile under biological conditions. SPAAC has found less use in materials science to date, − and with respect to SWNT work, only a single report has been published on the use of SPAAC to produce nanohybrids of covalently functionalized SWNTs and gold nanoparticles (AuNPs) . Here, we sought to combine the efficacy of noncovalent functionalization in preserving SWNT optoelectronic properties with the rapid and efficient chemistry of SPAAC.…”

Section: Introductionmentioning

confidence: 99%

Decoration of Polyfluorene-Wrapped Carbon Nanotubes via Strain-Promoted Azide–Alkyne Cycloaddition

et al. 2018

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Developing methodologies that can efficiently decorate carbon nanotube surfaces with various molecular structures while avoiding damage to nanotube optoelectronic properties is an ongoing challenge. Here, we outline a methodology to perform chemistry on the nanotube surface without perturbing optoelectronic properties. Reactive, noncovalently functionalized polymer–nanotube complexes were prepared using polyfluorene with azide groups in its side chains. The azides enable strain-promoted azide–alkyne cycloaddition to occur between polymer–nanotube complexes and small molecules or polymers derivatized with a strained cyclooctyne. This reaction was found to occur efficiently at room temperature, without any catalyst or byproduct removal required. The reaction was monitored by infrared spectroscopy via the disappearance of the polymer azide stretch at ∼2090 cm–1, and this chemistry resulted in no damage to the nanotube sidewall, as evidenced by Raman spectroscopy. The azide-containing polyfluorene was used to prepare an enriched dispersion of semiconducting carbon nanotubes in organic media, which could then be redispersed in aqueous solution post-click with strained cyclooctyne-functionalized poly(ethylene glycol). Taking advantage of the ability to preserve optoelectronic properties, solvatochromism of an identical subset of semiconducting carbon nanotubes was investigated using absorption, fluorescence, and Raman spectroscopy. It was found that, in aqueous media, fluorescence was nonuniformly quenched among the different semiconducting species and that there was a significant red-shift in the emission of all nanotubes in D2O relative to nonpolar toluene.

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Section: Introductionmentioning

confidence: 99%

Decoration of Polyfluorene-Wrapped Carbon Nanotubes via Strain-Promoted Azide–Alkyne Cycloaddition

et al. 2018

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“…Calcein AM was purchased from Abcam (ab141420). Azides A and B were synthesized according to a literature procedure. , Azide C was synthesized according to a protocol previously developed in our group …”

Section: Methodsmentioning

confidence: 99%

“…27,28 Azide C was synthesized according to a protocol previously developed in our group. 29 1 H, 13 C{ 1 H}, and 19 F{ 1 H} NMR spectra were recorded on Varian INOVA 400 (or 600) or Bruker AVANCE III HD 400 spectrometers using CDCl 3 or CD 3 OD as a solvent. Fourier transform infrared (FTIR) spectra were recorded using an attenuated total reflectance (ATR) attachment using a Bruker Vector 33 FTIR spectrometer.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Investigation of Au SAMs Photoclick Derivatization by PM-IRRAS

et al. 2020

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In this work we present a clean one-step process for modifying headgroups of selfassembled monolayers (SAMs) on gold using photo-enabled click chemistry. A thiolated, cyclopropenonecaged strained alkyne precursor was first functionalized onto a flat gold substrate through self-assembly. Exposure of the cyclopropenone SAM to UV-A light initiated the efficient photochemical decarbonylation of the cyclopropenone moiety, revealing the strained alkyne capable of undergoing the interfacial strainpromoted alkyne-azide cycloaddition (SPAAC). Irradiated SAMs were derivatized with a series of model azides with varied hydrophobicity to demonstrate the generality of this chemical system for the modification and fine-tuning of the surface chemistry on gold substrates. SAMs were characterized at each step with polarization-modulation infrared reflection-absorption spectroscopy (PM-IRRAS) to confirm successful functionalization and reactivity. Furthermore, to showcase the compatibility of this approach with biochemical applications, cyclopropenone SAMs were irradiated and modified with azide-bearing cell adhesion peptides to promote human fibroblast cell adhesion, then imaged by live cell fluorescence microscopy. Thus, the "photoclick" methodology reported here represents an improved, versatile, catalyst-free protocol that allows for a high degree of control over the modification of material surfaces, with applicability in materials science as well as biochemistry.

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“…[29][30] Azide C was synthesized according to a protocol previously developed in our group. 31 1 H, 13 C{ 1 H}, and 19 F{ 1 H} NMR spectra were recorded on Varian INOVA 400 (or 600) or Bruker AvIII HD 400 spectrometers using CDCl3 or CD3OD as solvent. FTIR spectra were recorded using an attenuated total reflectance (ATR) attachment using a Bruker Vector 33 FTIR spectrometer.…”

Section: Methodsmentioning

confidence: 99%

Investigation of Au SAMs Photoclick Derivatization by PM-IRRAS

Workentin

Lagugné‐Labarthet²,

Legge³

2019

Preprint

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In this work we present a clean one-step process for modifying headgroups of self-assembled monolayers (SAMs) on gold using photo-enabled click chemistry. A thiolated, cyclopropenone-caged strained alkyne precursor was first functionalized onto a flat gold substrate through self-assembly. Exposure of the cyclopropenone SAM to UV-A light initiated the efficient photochemical decarbonylation of the cyclopropenone moiety, revealing the strained alkyne capable of undergoing the interfacial strain-promoted alkyne-azide cycloaddition (SPAAC). Irradiated SAMs were derivatized with a series of model azides with varied hydrophobicity to demonstrate the generality of this chemical system for the modification and fine-tuning of the surface chemistry on gold substrates. SAMs were characterized at each step with polarization-modulation infrared reflection-absorption spectroscopy (PM-IRRAS) to confirm successful functionalization and reactivity. Furthermore, to showcase the compatibility of this approach with biochemical applications, cyclopropenone SAMs were irradiated and modified with azide-bearing cell adhesion peptides to promote human fibroblast cell adhesion, then imaged by live cell fluorescence microscopy. Thus, the “photoclick” methodology reported here represents an improved, versatile, catalyst-free protocol that allows for a high degree of control over the modification of material surfaces, with applicability in materials science as well as biochemistry.<br>

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Fluorogenic Gold Nanoparticle (AuNP) Substrate: A Model for the Controlled Release of Molecules from AuNP Nanocarriers via Interfacial Staudinger–Bertozzi Ligation

Cited by 16 publications

References 29 publications

Decoration of Polyfluorene-Wrapped Carbon Nanotubes via Strain-Promoted Azide–Alkyne Cycloaddition

Decoration of Polyfluorene-Wrapped Carbon Nanotubes via Strain-Promoted Azide–Alkyne Cycloaddition

Investigation of Au SAMs Photoclick Derivatization by PM-IRRAS

Investigation of Au SAMs Photoclick Derivatization by PM-IRRAS

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