Self-amplified depolymerization of oligo(thiourethanes) for the release of COS/H2S

Chadwick R. Powell; Jeffrey C. Foster; Sarah N. Swilley; Kuljeet Kaur; Samantha J. Scannelli; Diego Troya; John B. Matson

doi:10.1039/c9py00354a

Self-amplified depolymerization of oligo(thiourethanes) for the release of COS/H₂S

Chadwick R. Powell, Jeffrey C. Foster, Sarah N. Swilley, Kuljeet Kaur, Samantha J. Scannelli, Diego Troya, John B. Matson

Research output: Contribution to journal › Article › peer-review

24 Scopus citations

Abstract

Herein we report the self-amplified depolymerization of an aryl oligo(thiourethane) (OTU) for the release of COS/H₂S. The OTU was synthesized via polyaddition of 4-isothiocyanatobenzyl alcohol and end-capped with an aryl azide. The aryl azide chain-end was reduced by tris(2-carboxyethyl)phosphine or H₂S to the corresponding aniline, resulting in depolymerization (i.e., self-immolation) and the release of COS/H₂S. Depolymerization was monitored by ¹H NMR and UV-Vis spectroscopy, and the released COS was converted into H₂S by the ubiquitous enzyme carbonic anhydrase in aqueous media, generating an amplified response.

Original language	English
Pages (from-to)	2991-2995
Number of pages	5
Journal	Polymer Chemistry
Volume	10
Issue number	23
DOIs	https://doi.org/10.1039/c9py00354a
State	Published - Jun 21 2019
Externally published	Yes

Funding

This work was supported by the National Science Foundation (DMR-1454754), the National Institutes of Health (R01GM123508), and the Dreyfus foundation. The authors acknowledge Ryan Carrazzone for help with polymer analysis. Advanced Research Computing at Virginia Tech is gratefully acknowledged for providing computational resources and technical support that have contributed to the results reported within this paper.

Funders	Funder number
National Science Foundation	DMR-1454754
National Institutes of Health	R01GM123508
Camille and Henry Dreyfus Foundation

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title = "Self-amplified depolymerization of oligo(thiourethanes) for the release of COS/H2S",

abstract = "Herein we report the self-amplified depolymerization of an aryl oligo(thiourethane) (OTU) for the release of COS/H2S. The OTU was synthesized via polyaddition of 4-isothiocyanatobenzyl alcohol and end-capped with an aryl azide. The aryl azide chain-end was reduced by tris(2-carboxyethyl)phosphine or H2S to the corresponding aniline, resulting in depolymerization (i.e., self-immolation) and the release of COS/H2S. Depolymerization was monitored by 1H NMR and UV-Vis spectroscopy, and the released COS was converted into H2S by the ubiquitous enzyme carbonic anhydrase in aqueous media, generating an amplified response.",

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doi = "10.1039/c9py00354a",

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T1 - Self-amplified depolymerization of oligo(thiourethanes) for the release of COS/H2S

AU - Powell, Chadwick R.

AU - Foster, Jeffrey C.

AU - Swilley, Sarah N.

AU - Kaur, Kuljeet

AU - Scannelli, Samantha J.

AU - Troya, Diego

AU - Matson, John B.

PY - 2019/6/21

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N2 - Herein we report the self-amplified depolymerization of an aryl oligo(thiourethane) (OTU) for the release of COS/H2S. The OTU was synthesized via polyaddition of 4-isothiocyanatobenzyl alcohol and end-capped with an aryl azide. The aryl azide chain-end was reduced by tris(2-carboxyethyl)phosphine or H2S to the corresponding aniline, resulting in depolymerization (i.e., self-immolation) and the release of COS/H2S. Depolymerization was monitored by 1H NMR and UV-Vis spectroscopy, and the released COS was converted into H2S by the ubiquitous enzyme carbonic anhydrase in aqueous media, generating an amplified response.

AB - Herein we report the self-amplified depolymerization of an aryl oligo(thiourethane) (OTU) for the release of COS/H2S. The OTU was synthesized via polyaddition of 4-isothiocyanatobenzyl alcohol and end-capped with an aryl azide. The aryl azide chain-end was reduced by tris(2-carboxyethyl)phosphine or H2S to the corresponding aniline, resulting in depolymerization (i.e., self-immolation) and the release of COS/H2S. Depolymerization was monitored by 1H NMR and UV-Vis spectroscopy, and the released COS was converted into H2S by the ubiquitous enzyme carbonic anhydrase in aqueous media, generating an amplified response.

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ER -

Self-amplified depolymerization of oligo(thiourethanes) for the release of COS/H₂S

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