A mild, efficient and catalyst-free thermoreversible ligation system based on dithiooxalates

Kai Pahnke; Naomi L. Haworth; Josef Brandt; Uwe Paulmann; Christian Richter; Friedrich G. Schmidt; Albena Lederer; Michelle L. Coote; Christopher Barner-Kowollik

doi:10.1039/c6py00470a

A mild, efficient and catalyst-free thermoreversible ligation system based on dithiooxalates

Kai Pahnke, Naomi L. Haworth, Josef Brandt, Uwe Paulmann, Christian Richter, Friedrich G. Schmidt, Albena Lederer, Michelle L. Coote, Christopher Barner-Kowollik

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

7 Citations (Scopus)

Abstract

We demonstrate a novel and ready to prepare thermoreversible hetero Diels-Alder dilinker on the basis of dithiooxalates, enabling the mild, rapid and catalyst-free linkage of diverse diene species under ambient conditions for applications in the fields of, for example, modular ligation, self-healing or recyclable materials and surface modification amongst others. The linker was studied using quantum chemical calculations, and experimentally in small molecular reactions via UV/Vis spectroscopy, mass spectrometry and NMR as well as in step-growth polymerizations with diene-difunctional building blocks-characterized via (temperature dependent) SEC and HT NMR-as an example for efficient polymer ligation.

Original language	English
Pages (from-to)	3244-3250
Number of pages	7
Journal	Polymer Chemistry
Volume	7
Issue number	19
DOIs	https://doi.org/10.1039/c6py00470a
Publication status	Published - 21 May 2016
Externally published	Yes

Bibliographical note

Funding Information:
C. B.-K., M. L. C. and A. L. are grateful for continued support from and the excellent collaboration with Evonik Industries. C. B.-K. additionally acknowledges continued support from the KIT via the Helmholtz association (BIFTM and STN programs) as well as the German Research Council (DFG). M. L. C. acknowledges generous allocations of supercomputing time on the National Facility of the National Computational Infrastructure. The authors thank K. K. Oehlenschlaeger for fruitful discussions and J. Lenz for his help with the TD SEC characterization. K. P. acknowledges financial support from the Karlsruhe House of Young Scientists (KHYS) funding a research stay in the laboratories of M. L. C.

Publisher Copyright:
© The Royal Society of Chemistry 2016.

Keywords

catalyst-free
thermoreversible
ligation
system
dithiooxalates

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title = "A mild, efficient and catalyst-free thermoreversible ligation system based on dithiooxalates",

abstract = "We demonstrate a novel and ready to prepare thermoreversible hetero Diels-Alder dilinker on the basis of dithiooxalates, enabling the mild, rapid and catalyst-free linkage of diverse diene species under ambient conditions for applications in the fields of, for example, modular ligation, self-healing or recyclable materials and surface modification amongst others. The linker was studied using quantum chemical calculations, and experimentally in small molecular reactions via UV/Vis spectroscopy, mass spectrometry and NMR as well as in step-growth polymerizations with diene-difunctional building blocks-characterized via (temperature dependent) SEC and HT NMR-as an example for efficient polymer ligation.",

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author = "Kai Pahnke and Haworth, {Naomi L.} and Josef Brandt and Uwe Paulmann and Christian Richter and Schmidt, {Friedrich G.} and Albena Lederer and Coote, {Michelle L.} and Christopher Barner-Kowollik",

note = "Funding Information: C. B.-K., M. L. C. and A. L. are grateful for continued support from and the excellent collaboration with Evonik Industries. C. B.-K. additionally acknowledges continued support from the KIT via the Helmholtz association (BIFTM and STN programs) as well as the German Research Council (DFG). M. L. C. acknowledges generous allocations of supercomputing time on the National Facility of the National Computational Infrastructure. The authors thank K. K. Oehlenschlaeger for fruitful discussions and J. Lenz for his help with the TD SEC characterization. K. P. acknowledges financial support from the Karlsruhe House of Young Scientists (KHYS) funding a research stay in the laboratories of M. L. C. Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2016.",

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doi = "10.1039/c6py00470a",

language = "English",

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AU - Pahnke, Kai

AU - Haworth, Naomi L.

AU - Brandt, Josef

AU - Paulmann, Uwe

AU - Richter, Christian

AU - Schmidt, Friedrich G.

AU - Lederer, Albena

AU - Coote, Michelle L.

AU - Barner-Kowollik, Christopher

N1 - Funding Information: C. B.-K., M. L. C. and A. L. are grateful for continued support from and the excellent collaboration with Evonik Industries. C. B.-K. additionally acknowledges continued support from the KIT via the Helmholtz association (BIFTM and STN programs) as well as the German Research Council (DFG). M. L. C. acknowledges generous allocations of supercomputing time on the National Facility of the National Computational Infrastructure. The authors thank K. K. Oehlenschlaeger for fruitful discussions and J. Lenz for his help with the TD SEC characterization. K. P. acknowledges financial support from the Karlsruhe House of Young Scientists (KHYS) funding a research stay in the laboratories of M. L. C. Publisher Copyright: © The Royal Society of Chemistry 2016.

PY - 2016/5/21

Y1 - 2016/5/21

N2 - We demonstrate a novel and ready to prepare thermoreversible hetero Diels-Alder dilinker on the basis of dithiooxalates, enabling the mild, rapid and catalyst-free linkage of diverse diene species under ambient conditions for applications in the fields of, for example, modular ligation, self-healing or recyclable materials and surface modification amongst others. The linker was studied using quantum chemical calculations, and experimentally in small molecular reactions via UV/Vis spectroscopy, mass spectrometry and NMR as well as in step-growth polymerizations with diene-difunctional building blocks-characterized via (temperature dependent) SEC and HT NMR-as an example for efficient polymer ligation.

AB - We demonstrate a novel and ready to prepare thermoreversible hetero Diels-Alder dilinker on the basis of dithiooxalates, enabling the mild, rapid and catalyst-free linkage of diverse diene species under ambient conditions for applications in the fields of, for example, modular ligation, self-healing or recyclable materials and surface modification amongst others. The linker was studied using quantum chemical calculations, and experimentally in small molecular reactions via UV/Vis spectroscopy, mass spectrometry and NMR as well as in step-growth polymerizations with diene-difunctional building blocks-characterized via (temperature dependent) SEC and HT NMR-as an example for efficient polymer ligation.

KW - catalyst-free

KW - thermoreversible

KW - ligation

KW - system

KW - dithiooxalates

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DO - 10.1039/c6py00470a

M3 - Article

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SP - 3244

EP - 3250

JO - Polymer Chemistry

JF - Polymer Chemistry

SN - 1759-9962

IS - 19

ER -

A mild, efficient and catalyst-free thermoreversible ligation system based on dithiooxalates

Abstract

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Keywords

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