Di(benzothienyl)cyclobutenes: Toward Strained Photoswitchable Fluorophores

0532717 - ÚOCHB 2021 RIV DE eng J - Journal Article
Sysoiev, Dmytro - Procházková, Eliška - Semenenko, A. - Pohl, Radek - Shishkina, S. - Klepetářová, Blanka - Shvadchak, Volodymyr V. - Yushchenko, Dmytro A.
Di(benzothienyl)cyclobutenes: Toward Strained Photoswitchable Fluorophores.
ChemPlusChem. Roč. 85, č. 9 (2020), s. 2084-2092. ISSN 2192-6506. E-ISSN 2192-6506
R&D Projects: GA ČR(CZ) GA19-21318S
Institutional support: RVO:61388963
Keywords : cyclobutenes * diarylethene sulfones * dyes/pigments * photochromic reactions * photoswitches
OECD category: Organic chemistry
Impact factor: 2.863, year: 2020
Method of publishing: Limited access
https://doi.org/10.1002/cplu.202000481

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.
Permanent Link: http://hdl.handle.net/11104/0311162