---
OA_place: publisher
OA_type: hybrid
_id: '21805'
abstract:
- lang: eng
text: Donor–acceptor Stenhouse adducts (DASAs) are visible‐light‐responsive photoswitches
with a variety of emerging applications in photoresponsive materials. Their two‐step
modular synthesis, centered on the nucleophilic ring opening of an activated furan,
makes DASAs readily accessible. However, the use of less reactive donors or acceptors
renders the process slow and low yielding, which has limited their development.
We demonstrate here that 1,1,1,3,3,3‐hexafluoro‐2‐propanol (HFIP) promotes the
ring‐opening reaction and stabilizes the open isomer, allowing greatly reduced
reaction times and increased yields for known derivatives. In addition, it provides
access to previously unattainable DASA‐based photoswitches and DASA–polymer conjugates.
The role of HFIP and the photochromic properties of a set of new DASAs is probed
using a combination of 1H NMR and UV/Vis spectroscopy. The
use of sterically hindered, electron‐poor amines enabled the dark equilibrium
to be decoupled from closed‐isomer half‐lives for the first time.
article_processing_charge: No
article_type: original
author:
- first_name: Michèle
full_name: Clerc, Michèle
last_name: Clerc
- first_name: Friedrich J
full_name: Stricker, Friedrich J
id: 7aca2cfc-46cf-11f0-abd3-8c96b5186745
last_name: Stricker
- first_name: Sebastian
full_name: Ulrich, Sebastian
last_name: Ulrich
- first_name: Miranda
full_name: Sroda, Miranda
last_name: Sroda
- first_name: Nico
full_name: Bruns, Nico
last_name: Bruns
- first_name: Luciano F.
full_name: Boesel, Luciano F.
last_name: Boesel
- first_name: Javier
full_name: Read de Alaniz, Javier
last_name: Read de Alaniz
citation:
ama: Clerc M, Stricker FJ, Ulrich S, et al. Promoting the furan ring‐opening reaction
to access new donor-acceptor Stenhouse adducts with hexafluoroisopropanol. Angewandte
Chemie International Edition. 2021;60(18):10219-10227. doi:10.1002/anie.202100115
apa: Clerc, M., Stricker, F. J., Ulrich, S., Sroda, M., Bruns, N., Boesel, L. F.,
& Read de Alaniz, J. (2021). Promoting the furan ring‐opening reaction to
access new donor-acceptor Stenhouse adducts with hexafluoroisopropanol. Angewandte
Chemie International Edition. Wiley. https://doi.org/10.1002/anie.202100115
chicago: Clerc, Michèle, Friedrich J Stricker, Sebastian Ulrich, Miranda Sroda,
Nico Bruns, Luciano F. Boesel, and Javier Read de Alaniz. “Promoting the Furan
Ring‐opening Reaction to Access New Donor-Acceptor Stenhouse Adducts with Hexafluoroisopropanol.”
Angewandte Chemie International Edition. Wiley, 2021. https://doi.org/10.1002/anie.202100115.
ieee: M. Clerc et al., “Promoting the furan ring‐opening reaction to access
new donor-acceptor Stenhouse adducts with hexafluoroisopropanol,” Angewandte
Chemie International Edition, vol. 60, no. 18. Wiley, pp. 10219–10227, 2021.
ista: Clerc M, Stricker FJ, Ulrich S, Sroda M, Bruns N, Boesel LF, Read de Alaniz
J. 2021. Promoting the furan ring‐opening reaction to access new donor-acceptor
Stenhouse adducts with hexafluoroisopropanol. Angewandte Chemie International
Edition. 60(18), 10219–10227.
mla: Clerc, Michèle, et al. “Promoting the Furan Ring‐opening Reaction to Access
New Donor-Acceptor Stenhouse Adducts with Hexafluoroisopropanol.” Angewandte
Chemie International Edition, vol. 60, no. 18, Wiley, 2021, pp. 10219–27,
doi:10.1002/anie.202100115.
short: M. Clerc, F.J. Stricker, S. Ulrich, M. Sroda, N. Bruns, L.F. Boesel, J. Read
de Alaniz, Angewandte Chemie International Edition 60 (2021) 10219–10227.
date_created: 2026-05-06T10:42:50Z
date_published: 2021-04-26T00:00:00Z
date_updated: 2026-05-11T07:40:12Z
day: '26'
ddc:
- '540'
doi: 10.1002/anie.202100115
extern: '1'
external_id:
pmid:
- '33503292'
intvolume: ' 60'
issue: '18'
language:
- iso: eng
main_file_link:
- open_access: '1'
url: https://doi.org/10.1002/anie.202100115
month: '04'
oa: 1
oa_version: Published Version
page: 10219-10227
pmid: 1
publication: Angewandte Chemie International Edition
publication_identifier:
issn:
- 1521-3773
issnl:
- 1433-7851
publication_status: published
publisher: Wiley
quality_controlled: '1'
scopus_import: '1'
status: public
title: Promoting the furan ring‐opening reaction to access new donor-acceptor Stenhouse
adducts with hexafluoroisopropanol
tmp:
image: /images/cc_by.png
legal_code_url: https://creativecommons.org/licenses/by/4.0/legalcode
name: Creative Commons Attribution 4.0 International Public License (CC-BY 4.0)
short: CC BY (4.0)
type: journal_article
user_id: 2DF688A6-F248-11E8-B48F-1D18A9856A87
volume: 60
year: '2021'
...
---
_id: '8474'
abstract:
- lang: eng
text: Hydrogen bonds are ubiquitous interactions in proteins, and are important
for their folding and functionality. Scalar coupling constants across hydrogen
bonds in the protein backbone, some as small as 0.5 Hz, can be directly measured
in the solid state by NMR spectroscopy (see figure). The nuclei on both sides
of the hydrogen bond can be identified and the size of the coupling constant can
be measured accurately.
article_processing_charge: No
article_type: original
author:
- first_name: Paul
full_name: Schanda, Paul
id: 7B541462-FAF6-11E9-A490-E8DFE5697425
last_name: Schanda
orcid: 0000-0002-9350-7606
- first_name: Matthias
full_name: Huber, Matthias
last_name: Huber
- first_name: René
full_name: Verel, René
last_name: Verel
- first_name: Matthias
full_name: Ernst, Matthias
last_name: Ernst
- first_name: "Beatâ\x80\NH."
full_name: "Meier, Beatâ\x80\NH."
last_name: Meier
citation:
ama: Schanda P, Huber M, Verel R, Ernst M, Meier B. Direct detection of 3hJN’ hydrogen-bond
scalar couplings in proteins by solid-state NMR spectroscopy. Angewandte Chemie
International Edition. 2009;48(49):9322-9325. doi:10.1002/anie.200904411
apa: Schanda, P., Huber, M., Verel, R., Ernst, M., & Meier, B. (2009). Direct
detection of 3hJN’ hydrogen-bond scalar couplings in proteins by solid-state NMR
spectroscopy. Angewandte Chemie International Edition. Wiley. https://doi.org/10.1002/anie.200904411
chicago: "Schanda, Paul, Matthias Huber, René Verel, Matthias Ernst, and Beatâ\x80\NH.
Meier. “Direct Detection of 3hJN’ Hydrogen-Bond Scalar Couplings in Proteins by
Solid-State NMR Spectroscopy.” Angewandte Chemie International Edition.
Wiley, 2009. https://doi.org/10.1002/anie.200904411."
ieee: P. Schanda, M. Huber, R. Verel, M. Ernst, and B. Meier, “Direct detection
of 3hJN’ hydrogen-bond scalar couplings in proteins by solid-state NMR spectroscopy,”
Angewandte Chemie International Edition, vol. 48, no. 49. Wiley, pp. 9322–9325,
2009.
ista: Schanda P, Huber M, Verel R, Ernst M, Meier B. 2009. Direct detection of 3hJN’
hydrogen-bond scalar couplings in proteins by solid-state NMR spectroscopy. Angewandte
Chemie International Edition. 48(49), 9322–9325.
mla: Schanda, Paul, et al. “Direct Detection of 3hJN’ Hydrogen-Bond Scalar Couplings
in Proteins by Solid-State NMR Spectroscopy.” Angewandte Chemie International
Edition, vol. 48, no. 49, Wiley, 2009, pp. 9322–25, doi:10.1002/anie.200904411.
short: P. Schanda, M. Huber, R. Verel, M. Ernst, B. Meier, Angewandte Chemie International
Edition 48 (2009) 9322–9325.
date_created: 2020-09-18T10:11:33Z
date_published: 2009-11-17T00:00:00Z
date_updated: 2021-01-12T08:19:31Z
day: '17'
doi: 10.1002/anie.200904411
extern: '1'
intvolume: ' 48'
issue: '49'
keyword:
- General Chemistry
- Catalysis
language:
- iso: eng
month: '11'
oa_version: None
page: 9322-9325
publication: Angewandte Chemie International Edition
publication_identifier:
issn:
- 1433-7851
- 1521-3773
publication_status: published
publisher: Wiley
quality_controlled: '1'
status: public
title: Direct detection of 3hJN' hydrogen-bond scalar couplings in proteins by solid-state
NMR spectroscopy
type: journal_article
user_id: 2DF688A6-F248-11E8-B48F-1D18A9856A87
volume: 48
year: '2009'
...