Di(benzothienyl)cyclobutenes: Toward Strained Photoswitchable Fluorophores

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F20%3A00532717" target="_blank" >RIV/61388963:_____/20:00532717 - isvavai.cz</a>

Výsledek na webu

<a href="https://doi.org/10.1002/cplu.202000481" target="_blank" >https://doi.org/10.1002/cplu.202000481</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/cplu.202000481" target="_blank" >10.1002/cplu.202000481</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Di(benzothienyl)cyclobutenes: Toward Strained Photoswitchable Fluorophores

Popis výsledku v původním jazyce

Bis(benzothienyl)ethene sulfones are very interesting molecules for super-resolution microscopy due to their photoswitching properties. However, functionalization of the 'classical' bis(benzothienyl)ethene sulfones with a five-membered central ring leads to significant decrease of quantum yields of photoconversion of the fluorescent closed form of the dye to the non-fluorescent open form that limits their application in microscopy. Here, we designed and synthesized diarylethenes with a fluorinated four-membered central ring that adds extra strain to the closed form of the dye. The reaction mechanism of their formation was studied, and byproducts formed upon structural rearrangement of the benzothiophene fragment were characterized. The photochromic properties of the new molecules were investigated by NMR and absorption spectroscopy. Some of these compounds show enhanced tendency to ring opening and have quantum yields of the ring-opening reaction in the range of 0.2-0.5.

Název v anglickém jazyce

Di(benzothienyl)cyclobutenes: Toward Strained Photoswitchable Fluorophores

Popis výsledku anglicky

Bis(benzothienyl)ethene sulfones are very interesting molecules for super-resolution microscopy due to their photoswitching properties. However, functionalization of the 'classical' bis(benzothienyl)ethene sulfones with a five-membered central ring leads to significant decrease of quantum yields of photoconversion of the fluorescent closed form of the dye to the non-fluorescent open form that limits their application in microscopy. Here, we designed and synthesized diarylethenes with a fluorinated four-membered central ring that adds extra strain to the closed form of the dye. The reaction mechanism of their formation was studied, and byproducts formed upon structural rearrangement of the benzothiophene fragment were characterized. The photochromic properties of the new molecules were investigated by NMR and absorption spectroscopy. Some of these compounds show enhanced tendency to ring opening and have quantum yields of the ring-opening reaction in the range of 0.2-0.5.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

<a href="/cs/project/GA19-21318S" target="_blank" >GA19-21318S: Objasnění role diacylglycerolů v regulaci sekrece inzulínu z beta buněk</a><br>

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2020

Kód důvěrnosti údajů

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

Název periodika

ChemPlusChem

ISSN

2192-6506

e-ISSN

—

Svazek periodika

85

Číslo periodika v rámci svazku

9

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

9

Strana od-do

2084-2092

Kód UT WoS článku

000573610000016

EID výsledku v databázi Scopus

2-s2.0-85091053866