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ChemistryOpen. 2019 Mar 6;8(3):304-315. doi: 10.1002/open.201900029. eCollection 2019 Mar.

A Rational Approach to Tetra-Functional Photo-Switches.

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1
Universität Bielefeld, Fakultät für Chemie, Lehrstuhl für Anorganische Chemie und Strukturchemie Centrum für Molekulare Materialien CM2 Universitätsstraße 25 33615 Bielefeld Germany.

Abstract

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-Bis{1,8-bis[(trimethylstannyl)ethynyl]anthracen-10-yl}propane served as model compound for photo-switchable acceptor molecules and its open and closed forms were characterized by NMR and DOSY experiments.

KEYWORDS:

Anthracenes; Cycloreversion; C−C-Bond Formation; Photo-switches; Photocyclomerization

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