English
 
User Manual Privacy Policy Disclaimer Contact us
  Advanced SearchBrowse

Item

ITEM ACTIONSEXPORT
  Mono- and bithiophene-substituted diarylethene photoswitches with emissive open or closed forms.

Schleper, A. L., Bossi, M. L., Belov, V. N., & Hell, S. W. (2019). Mono- and bithiophene-substituted diarylethene photoswitches with emissive open or closed forms. Beilstein Journal of Organic Chemistry, 15, 2344-2354. doi:10.3762/bjoc.15.227.

Item is

Basic

show hide
Item Permalink: http://hdl.handle.net/21.11116/0000-0005-3A64-A Version Permalink: http://hdl.handle.net/21.11116/0000-0005-3A68-6
Genre: Journal Article

Files

show Files
hide Files
:
3177356.pdf (Publisher version), 2MB
Name:
3177356.pdf
Description:
-
Visibility:
Public
MIME-Type / Checksum:
application/pdf / [MD5]
Technical Metadata:
Copyright Date:
-
Copyright Info:
-
License:
-
:
3177356_Suppl.htm (Supplementary material), 130KB
Name:
3177356_Suppl.htm
Description:
-
Visibility:
Public
MIME-Type / Checksum:
application/xhtml+xml / [MD5]
Technical Metadata:
Copyright Date:
-
Copyright Info:
-
License:
-

Locators

show

Creators

show
hide
 Creators:
Schleper, A. L., Author
Bossi, M. L.1, Author              
Belov, V. N.1, Author              
Hell, S. W.2, Author              
Affiliations:
1Department of NanoBiophotonics, MPI for biophysical chemistry, Max Planck Society, ou_578627              
2Department of NanoBiophotonics, MPI for Biophysical Chemistry, Max Planck Society, ou_578627              

Content

show
hide
Free keywords: diarylethenes; dyes; fluorescence; organic synthesis; photochromism; photoswitching
 Abstract: We present a new series of photochromic 1,2-bis(2-ethylbenzo[b]thiophen-3-yl)perfluorocyclopentenes with an oxidized benzothiophene core (O) or a nonoxidized one, decorated with mono- (Th1) and bithiophene (Th2) units attached to positions 6 and 6' (Sy = symmetric) or only to position 6 (As = asymmetric). "Oxidized" compounds have highly fluorescent closed forms emitting in the visible region (yellow to red). The dyes with nonoxidized benzothiophenes possess fluorescent open forms with rather low emission efficiency. The photoswitching kinetics was studied at several wavelengths with UV and visible light. New diarylethenes underwent ring-closure reactions by irradiation with UV light (365 nm, 405 nm), and the reversible ring-opening by irradiation with visible light (470 nm, 530 nm). The on-switching of fluorescence due to the ring-closure reaction was observed also with visible light of 470 nm (to an extent of 10% for compound SyOTh 1 ) and attributed to the Urbach tail effect. Due to a high degree of fluorescence modulation (>270), good fatigue resistance and large fluorescence quantum yield, compound SyOTh 1 emerged as a candidate for single-molecule based super-resolution fluorescence microscopy.

Details

show
hide
Language(s): eng - English
 Dates: 2019-10-01
 Publication Status: Published online
 Pages: -
 Publishing info: -
 Table of Contents: -
 Rev. Method: Peer
 Identifiers: DOI: 10.3762/bjoc.15.227
 Degree: -

Event

show

Legal Case

show

Project information

show

Source 1

show
hide
Title: Beilstein Journal of Organic Chemistry
Source Genre: Journal
 Creator(s):
Affiliations:
Publ. Info: -
Pages: - Volume / Issue: 15 Sequence Number: - Start / End Page: 2344 - 2354 Identifier: -