Rotaxanation as a sequestering template to preclude incidental metal insertion in complex oligochromophores

Huynh Thien Ngo; James E.M. Lewis; Daniel T. Payne; Francis D'Souza; Jonathan P. Hill; Katsuhiko Ariga; Genki Yoshikawa; Stephen M. Goldup

doi:10.1039/c9cc09681g

Rotaxanation as a sequestering template to preclude incidental metal insertion in complex oligochromophores

Huynh Thien Ngo^*, James E.M. Lewis, Daniel T. Payne, Francis D'Souza, Jonathan P. Hill, Katsuhiko Ariga, Genki Yoshikawa, Stephen M. Goldup

^*Corresponding author for this work

Chemistry

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

Abstract

The high yielding CuI-mediated click reaction is an effective procedure for the preparation of oligoporphyrinoid conjugates. However, the CuI catalyst leads to the adventitious and usually undesirable insertion of Cu ions into any non-metalated porphyrinoid centers during reaction. Here we report a "sacrificial rotaxane"strategy for the multifunctionalization of porphyrins with free base corroles without incidental copper insertion. This strategy can be considered a general method for implementing CuI-mediated click reactions with metal cation sequestration to avoid detrimental effects caused by the presence of copper cations.

Original language	English
Pages (from-to)	7447-7450
Number of pages	4
Journal	Chemical Communications
Volume	56
Issue number	54
DOIs	https://doi.org/10.1039/c9cc09681g
Publication status	Published - 11 Jul 2020

Bibliographical note

Funding Information:
This work was supported by the MSS alliance; a Grant-in-Aid for Research Activity Start-up, 17H07350, Ministry of Education, Culture, Sports, Science and Technology (MEXT), Japan; CREST JPMJCR1665, Japan Science and Technology (JST), Japan; the World Premier International Research Center Initiative (WPI) on Materials Nanoarchitectonics (MANA). JEML thanks the European Union for a Marie Skłodowska-Curie Fellowship (agreement no. 660731) and Imperial College London for an Imperial College Research Fellowship.

Publisher Copyright:
© The Royal Society of Chemistry.

ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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title = "Rotaxanation as a sequestering template to preclude incidental metal insertion in complex oligochromophores",

abstract = "The high yielding CuI-mediated click reaction is an effective procedure for the preparation of oligoporphyrinoid conjugates. However, the CuI catalyst leads to the adventitious and usually undesirable insertion of Cu ions into any non-metalated porphyrinoid centers during reaction. Here we report a {"}sacrificial rotaxane{"}strategy for the multifunctionalization of porphyrins with free base corroles without incidental copper insertion. This strategy can be considered a general method for implementing CuI-mediated click reactions with metal cation sequestration to avoid detrimental effects caused by the presence of copper cations.",

author = "Ngo, {Huynh Thien} and Lewis, {James E.M.} and Payne, {Daniel T.} and Francis D'Souza and Hill, {Jonathan P.} and Katsuhiko Ariga and Genki Yoshikawa and Goldup, {Stephen M.}",

note = "Funding Information: This work was supported by the MSS alliance; a Grant-in-Aid for Research Activity Start-up, 17H07350, Ministry of Education, Culture, Sports, Science and Technology (MEXT), Japan; CREST JPMJCR1665, Japan Science and Technology (JST), Japan; the World Premier International Research Center Initiative (WPI) on Materials Nanoarchitectonics (MANA). JEML thanks the European Union for a Marie Sk{\l}odowska-Curie Fellowship (agreement no. 660731) and Imperial College London for an Imperial College Research Fellowship. Publisher Copyright: {\textcopyright} The Royal Society of Chemistry.",

year = "2020",

month = jul,

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doi = "10.1039/c9cc09681g",

language = "English",

volume = "56",

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journal = "Chemical Communications",

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T1 - Rotaxanation as a sequestering template to preclude incidental metal insertion in complex oligochromophores

AU - Ngo, Huynh Thien

AU - Lewis, James E.M.

AU - Payne, Daniel T.

AU - D'Souza, Francis

AU - Hill, Jonathan P.

AU - Ariga, Katsuhiko

AU - Yoshikawa, Genki

AU - Goldup, Stephen M.

N1 - Funding Information: This work was supported by the MSS alliance; a Grant-in-Aid for Research Activity Start-up, 17H07350, Ministry of Education, Culture, Sports, Science and Technology (MEXT), Japan; CREST JPMJCR1665, Japan Science and Technology (JST), Japan; the World Premier International Research Center Initiative (WPI) on Materials Nanoarchitectonics (MANA). JEML thanks the European Union for a Marie Skłodowska-Curie Fellowship (agreement no. 660731) and Imperial College London for an Imperial College Research Fellowship. Publisher Copyright: © The Royal Society of Chemistry.

PY - 2020/7/11

Y1 - 2020/7/11

N2 - The high yielding CuI-mediated click reaction is an effective procedure for the preparation of oligoporphyrinoid conjugates. However, the CuI catalyst leads to the adventitious and usually undesirable insertion of Cu ions into any non-metalated porphyrinoid centers during reaction. Here we report a "sacrificial rotaxane"strategy for the multifunctionalization of porphyrins with free base corroles without incidental copper insertion. This strategy can be considered a general method for implementing CuI-mediated click reactions with metal cation sequestration to avoid detrimental effects caused by the presence of copper cations.

AB - The high yielding CuI-mediated click reaction is an effective procedure for the preparation of oligoporphyrinoid conjugates. However, the CuI catalyst leads to the adventitious and usually undesirable insertion of Cu ions into any non-metalated porphyrinoid centers during reaction. Here we report a "sacrificial rotaxane"strategy for the multifunctionalization of porphyrins with free base corroles without incidental copper insertion. This strategy can be considered a general method for implementing CuI-mediated click reactions with metal cation sequestration to avoid detrimental effects caused by the presence of copper cations.

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JO - Chemical Communications

JF - Chemical Communications

IS - 54

ER -

Rotaxanation as a sequestering template to preclude incidental metal insertion in complex oligochromophores

Abstract

Bibliographical note

ASJC Scopus subject areas

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