Synthesis of Functionalized Azobiphenyl- and Azoterphenyl- Ditopic Linkers : Modular Building Blocks for Photoresponsive Smart Materials

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Grosjean , S , Hodapp , P , Hassan , Z , Woell , C , Nieger , M & Bräse , S 2019 , ' Synthesis of Functionalized Azobiphenyl- and Azoterphenyl- Ditopic Linkers : Modular Building Blocks for Photoresponsive Smart Materials ' , Chemistryopen , vol. 8 , no. 6 , pp. 743-759 . https://doi.org/10.1002/open.201900031

Title: Synthesis of Functionalized Azobiphenyl- and Azoterphenyl- Ditopic Linkers : Modular Building Blocks for Photoresponsive Smart Materials
Author: Grosjean, Sylvain; Hodapp, Patrick; Hassan, Zahid; Woell, Christof; Nieger, Martin; Bräse, Stefan
Contributor: University of Helsinki, Department of Chemistry
Date: 2019-06
Language: eng
Number of pages: 17
Belongs to series: Chemistryopen
ISSN: 2191-1363
URI: http://hdl.handle.net/10138/304656
Abstract: Modular synthesis of structurally diverse functionalized azobiphenyls and azoterphenyls for the realization of optically switchable materials has been described. The corresponding synthesis of azobiphenyls and azoterphenyls by stepwise Mills/Suzuki-Miyaura cross-coupling reaction, proceeds with high yields and provides facile access to a library of functionalized building blocks. The synthetic methods described herein allow combining several distinct functional groups within a single unit, each intended for a specific task, such as 1) the -N=N- azobenzene core as a photoswitchable moiety, 2) aryls and heteroaryls, functionalized with carboxylic acids or pyridine at its peripheries, as coordinating moieties and 3) varying substitution, size and length of the backbone for adaptability to specific applications. These specifically designed azobiphenyls and azoterphenyls provide modular bricks, potentially useful for the assembly of a variety of polymers, molecular containers and coordination networks, offering a high degree of molecular functionality. Once integrated into materials, the azobenzene system, as a side group on the organic linker backbone, can be exploited for remotely controlling the structural, mechanical or physical properties, thus being applicable for a broad variety of 'smart' applications.
Subject: Azobenzene
modular synthesis
Mills reaction
building-blocks strategy
photoswitches
METAL-ORGANIC FRAMEWORKS
OPTICAL CONTROL
THIN-FILMS
LIGHT
SWITCHES
GUEST
CRYSTALS
ADSORPTION
INHIBITORS
RECEPTOR
116 Chemical sciences
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