Journal Article

A Rational Approach to Tetra‐Functional Photo‐Switches

Neumann, Beate, Mitzel, Norbert W., Stammler, Hans‐Georg, Lamm, Jan‐Hendrik, Niermeier, Philipp, Mix, Andreas

2019

Overview

α,ω‐Bis(1,8‐dichloroanthracen‐10‐yl)alkanes with (CH2)n‐linker units (n=1–4) were synthesized starting from 1,8‐dichloroanthracen‐10(9H)‐one. This was transformed into anthracenes with allyl, bromomethyl and propargyl substituents in position 10; these were converted in various C−C‐bond formation reactions (plus hydrogenation), leading to two anthracene units flexibly linked by α,ω‐alkandiyl groups. 1,2‐Ethandiyl‐ and 1,3‐propandiyl‐linked derivatives were functionalized with ethynyl groups in positions 1, 8, 1’ and 8’, and these terminally functionalized by Me3Sn groups using Me2NSnMe3. All linked bisanthracenes were subjected to UV light induced cyclomerization and a series of 9,10 : 9’,10’‐photo‐cyclomers were obtained. Their thermal cycloreversion and (repeated) switchability was demonstrated. 1,3‐Bis1,8‐bis[(trimethylstannyl)ethynyl]anthracen‐10‐ylpropane served as model compound for photo‐switchable acceptor molecules and its open and closed forms were characterized by NMR and DOSY experiments. Light on the switch: Linked bisanthracenes bearing four (partly metal‐containing) substituents undergo photo‐cyclomerization that enables the parallelization of all four functions and can be thermally reopened by cycloreversion which allows repeated switchability.

• Publisher: John Wiley & Sons, Inc,John Wiley and Sons Inc,Wiley-VCH
• Subject: Alkanes / Anthracene / Anthracenes / Cycloreversion / C−C-Bond Formation / Experiments / Mass spectrometry / NMR / Nuclear magnetic resonance / Photo-switches / Photocyclomerization / Scientific imaging / Switches / Ultraviolet radiation