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General Method to Increase Carboxylic Acid Content on Nanodiamonds

Carboxylic acid is a commonly utilized functional group for covalent surface conjugation of carbon nanoparticles that is typically generated by acid oxidation. However, acid oxidation generates additional oxygen containing groups, including epoxides, ketones, aldehydes, lactones, and alcohols. We pr...

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Autores principales: Shenoy, Ganesh, Ettedgui, Jessica, Mushti, Chandrasekhar, Hong, Jennifer, Lane, Kelly, Blackman, Burchelle, Jung, Hak-Sung, Takagi, Yasuharu, Seol, Yeonee, Brechbiel, Martin, Swenson, Rolf E., Neuman, Keir C.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8838522/
https://www.ncbi.nlm.nih.gov/pubmed/35164002
http://dx.doi.org/10.3390/molecules27030736
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author Shenoy, Ganesh
Ettedgui, Jessica
Mushti, Chandrasekhar
Hong, Jennifer
Lane, Kelly
Blackman, Burchelle
Jung, Hak-Sung
Takagi, Yasuharu
Seol, Yeonee
Brechbiel, Martin
Swenson, Rolf E.
Neuman, Keir C.
author_facet Shenoy, Ganesh
Ettedgui, Jessica
Mushti, Chandrasekhar
Hong, Jennifer
Lane, Kelly
Blackman, Burchelle
Jung, Hak-Sung
Takagi, Yasuharu
Seol, Yeonee
Brechbiel, Martin
Swenson, Rolf E.
Neuman, Keir C.
author_sort Shenoy, Ganesh
collection PubMed
description Carboxylic acid is a commonly utilized functional group for covalent surface conjugation of carbon nanoparticles that is typically generated by acid oxidation. However, acid oxidation generates additional oxygen containing groups, including epoxides, ketones, aldehydes, lactones, and alcohols. We present a method to specifically enrich the carboxylic acid content on fluorescent nanodiamond (FND) surfaces. Lithium aluminum hydride is used to reduce oxygen containing surface groups to alcohols. The alcohols are then converted to carboxylic acids through a rhodium (II) acetate catalyzed carbene insertion reaction with tert–butyl diazoacetate and subsequent ester cleavage with trifluoroacetic acid. This carboxylic acid enrichment process significantly enhanced nanodiamond homogeneity and improved the efficiency of functionalizing the FND surface. Biotin functionalized fluorescent nanodiamonds were demonstrated to be robust and stable single-molecule fluorescence and optical trapping probes.
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spelling pubmed-88385222022-02-13 General Method to Increase Carboxylic Acid Content on Nanodiamonds Shenoy, Ganesh Ettedgui, Jessica Mushti, Chandrasekhar Hong, Jennifer Lane, Kelly Blackman, Burchelle Jung, Hak-Sung Takagi, Yasuharu Seol, Yeonee Brechbiel, Martin Swenson, Rolf E. Neuman, Keir C. Molecules Article Carboxylic acid is a commonly utilized functional group for covalent surface conjugation of carbon nanoparticles that is typically generated by acid oxidation. However, acid oxidation generates additional oxygen containing groups, including epoxides, ketones, aldehydes, lactones, and alcohols. We present a method to specifically enrich the carboxylic acid content on fluorescent nanodiamond (FND) surfaces. Lithium aluminum hydride is used to reduce oxygen containing surface groups to alcohols. The alcohols are then converted to carboxylic acids through a rhodium (II) acetate catalyzed carbene insertion reaction with tert–butyl diazoacetate and subsequent ester cleavage with trifluoroacetic acid. This carboxylic acid enrichment process significantly enhanced nanodiamond homogeneity and improved the efficiency of functionalizing the FND surface. Biotin functionalized fluorescent nanodiamonds were demonstrated to be robust and stable single-molecule fluorescence and optical trapping probes. MDPI 2022-01-23 /pmc/articles/PMC8838522/ /pubmed/35164002 http://dx.doi.org/10.3390/molecules27030736 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Shenoy, Ganesh
Ettedgui, Jessica
Mushti, Chandrasekhar
Hong, Jennifer
Lane, Kelly
Blackman, Burchelle
Jung, Hak-Sung
Takagi, Yasuharu
Seol, Yeonee
Brechbiel, Martin
Swenson, Rolf E.
Neuman, Keir C.
General Method to Increase Carboxylic Acid Content on Nanodiamonds
title General Method to Increase Carboxylic Acid Content on Nanodiamonds
title_full General Method to Increase Carboxylic Acid Content on Nanodiamonds
title_fullStr General Method to Increase Carboxylic Acid Content on Nanodiamonds
title_full_unstemmed General Method to Increase Carboxylic Acid Content on Nanodiamonds
title_short General Method to Increase Carboxylic Acid Content on Nanodiamonds
title_sort general method to increase carboxylic acid content on nanodiamonds
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8838522/
https://www.ncbi.nlm.nih.gov/pubmed/35164002
http://dx.doi.org/10.3390/molecules27030736
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