Getting a molecular grip on the half-lives of iminothioindoxyls photoswitches

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15640%2F24%3A73625967" target="_blank" >RIV/61989592:15640/24:73625967 - isvavai.cz</a>

Result on the web

<a href="https://pubs.rsc.org/en/content/articlelanding/2024/sc/d4sc01457j" target="_blank" >https://pubs.rsc.org/en/content/articlelanding/2024/sc/d4sc01457j</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1039/d4sc01457j" target="_blank" >10.1039/d4sc01457j</a>

Result language

angličtina

Original language name

Getting a molecular grip on the half-lives of iminothioindoxyls photoswitches

Original language description

Visible-light-operated photoswitches are of growing interest in reversibly controlling molecular processes, enabling for example the precise spatiotemporal focusing of drug activity and manipulating the properties of materials. Therefore, many research efforts have been spent on seeking control over the (photo)physical properties of photoswitches, in particular the absorption maxima and the half-life. For photopharmacological applications, photoswitches should ideally be operated by visible light in at least one direction, and feature a metastable isomer with a half-life of 0.1-10 seconds. Here we present our efforts towards the engineering of the half-life of iminothioindoxyl (ITI) photoswitches, a recently discovered class of visible-light-responsive photochromes, whose applicability was hitherto limited by half-lives in the low millisecond range. Through the synthesis and characterization of a library of ITI photoswitches, we discovered variants with a substantially increased thermal stability, reaching half-lives of up to 0.2 seconds. Based on spectroscopic and computational analyses, we demonstrate how different substituent positions on the ITI molecule can be used to tune its photophysical properties independently to fit the desired application. Additionally, the unique reactivity of the ITI derivative that featured a perfluoro-aromatic ring and had the most long-lived metastable state was shown to be useful for labeling of nucleophilic functional groups. The present research thus paves the way for using ITI photoswitches in photopharmacology and chemical biology.

Czech name

—

Czech description

—

Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

—

OECD FORD branch

10401 - Organic chemistry

Project

<a href="/en/project/EH22_008%2F0004587" target="_blank" >EH22_008/0004587: Technology Beyond Nanoscale</a><br>

Continuities

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year

2024

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

Chemical Science

ISSN

2041-6520

e-ISSN

2041-6539

Volume of the periodical

15

Issue of the periodical within the volume

35

Country of publishing house

GB - UNITED KINGDOM

Number of pages

11

Pages from-to

14379-14389

UT code for WoS article

001290803000001

EID of the result in the Scopus database

2-s2.0-85201406737