Redshifted and thermally bistable one-way quantitative hemithioindigo-derived photoswitches enabled by isomer-specific excited state intramolecular proton transfer

Mikkel Krell-Jørgensen; Habiburrahman Zulfikri; Magnus Grage Bonnevie; Frederik Simonsen Bro; Asmus Ougaard Dohn; Luca Laraia

doi:10.1039/d2cc05548a

Redshifted and thermally bistable one-way quantitative hemithioindigo-derived photoswitches enabled by isomer-specific excited state intramolecular proton transfer

Mikkel Krell-Jørgensen
, Habiburrahman Zulfikri
, Magnus Grage Bonnevie
, Frederik Simonsen Bro
, Asmus Ougaard Dohn
, Luca Laraia^*

^*Corresponding author for this work

Research output: Contribution to journal › Journal article › Research › peer-review

Abstract

We report bistable indole-containing hemithioindigos (HTIs) with one-way quantitative photoswitching properties. Supported by state-averaged CASPT2/CASSCF calculations, we propose a mechanism for the observed one-way photoswitching that involves an isomer-specific excited state intramolecular proton transfer (ESIPT). Additionally, we developed a thermally bistable oligomer-inspired bipyrrole-containing HTI, which displays large band separation and bidirectional near-quantitative photoisomerization in the near-infrared, bio-optical window.

Original language	English
Journal	Chemical Communications
Volume	59
Pages (from-to)	563-566
ISSN	1359-7345
DOIs	https://doi.org/10.1039/d2cc05548a
Publication status	Published - 2023

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@article{85e4bef6d69d451c9fc9dff4bfcfebee,

title = "Redshifted and thermally bistable one-way quantitative hemithioindigo-derived photoswitches enabled by isomer-specific excited state intramolecular proton transfer",

abstract = "We report bistable indole-containing hemithioindigos (HTIs) with one-way quantitative photoswitching properties. Supported by state-averaged CASPT2/CASSCF calculations, we propose a mechanism for the observed one-way photoswitching that involves an isomer-specific excited state intramolecular proton transfer (ESIPT). Additionally, we developed a thermally bistable oligomer-inspired bipyrrole-containing HTI, which displays large band separation and bidirectional near-quantitative photoisomerization in the near-infrared, bio-optical window.",

author = "Mikkel Krell-J{\o}rgensen and Habiburrahman Zulfikri and Bonnevie, \{Magnus Grage\} and Bro, \{Frederik Simonsen\} and Dohn, \{Asmus Ougaard\} and Luca Laraia",

year = "2023",

doi = "10.1039/d2cc05548a",

language = "English",

volume = "59",

pages = "563--566",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

}

Redshifted and thermally bistable one-way quantitative hemithioindigo-derived photoswitches enabled by isomer-specific excited state intramolecular proton transfer. / Krell-Jørgensen, Mikkel; Zulfikri, Habiburrahman; Bonnevie, Magnus Grage et al.
In: Chemical Communications, Vol. 59, 2023, p. 563-566.

Research output: Contribution to journal › Journal article › Research › peer-review

TY - JOUR

T1 - Redshifted and thermally bistable one-way quantitative hemithioindigo-derived photoswitches enabled by isomer-specific excited state intramolecular proton transfer

AU - Krell-Jørgensen, Mikkel

AU - Zulfikri, Habiburrahman

AU - Bonnevie, Magnus Grage

AU - Bro, Frederik Simonsen

AU - Dohn, Asmus Ougaard

AU - Laraia, Luca

PY - 2023

Y1 - 2023

N2 - We report bistable indole-containing hemithioindigos (HTIs) with one-way quantitative photoswitching properties. Supported by state-averaged CASPT2/CASSCF calculations, we propose a mechanism for the observed one-way photoswitching that involves an isomer-specific excited state intramolecular proton transfer (ESIPT). Additionally, we developed a thermally bistable oligomer-inspired bipyrrole-containing HTI, which displays large band separation and bidirectional near-quantitative photoisomerization in the near-infrared, bio-optical window.

AB - We report bistable indole-containing hemithioindigos (HTIs) with one-way quantitative photoswitching properties. Supported by state-averaged CASPT2/CASSCF calculations, we propose a mechanism for the observed one-way photoswitching that involves an isomer-specific excited state intramolecular proton transfer (ESIPT). Additionally, we developed a thermally bistable oligomer-inspired bipyrrole-containing HTI, which displays large band separation and bidirectional near-quantitative photoisomerization in the near-infrared, bio-optical window.

U2 - 10.1039/d2cc05548a

DO - 10.1039/d2cc05548a

M3 - Journal article

C2 - 36537010

SN - 1359-7345

VL - 59

SP - 563

EP - 566

JO - Chemical Communications

JF - Chemical Communications

ER -

Redshifted and thermally bistable one-way quantitative hemithioindigo-derived photoswitches enabled by isomer-specific excited state intramolecular proton transfer

Abstract

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