Propeller‐Shaped D3h‐Symmetric Macrocycles with Three 1,8‐Diazaanthracene Blades as Building Blocks for Photochemically Induced Growth Reactions

Publisher: John Wiley & Sons Inc

E-ISSN: 1099-0690|2015|20|4519-4523

ISSN: 1434-193x

Source: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Vol.2015, Iss.20, 2015-07, pp. : 4519-4523

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Abstract

AbstractThe efficient synthesis of new D3h‐symmetric propeller‐shaped, double‐decker compounds with three vertically standing diazaanthracene units arranged so as to allow for photochemically induced intermolecular growth reaction by [4+4] cycloaddition is presented. The propellers bear alkyl chains of four different lengths (ethyl, propyl, hexyl, dodecyl) to have flexibility in creating ordered arrays by packing them into single crystals, onto solid substrates or into mesophases. All propellers are obtained in only six steps and on a 50–200 mg scale. The sequence passes through the ditriflated 1,8‐diazaanthracene derivatives 6 which are a very versatile building block for many purposes and were therefore synthesized on a 30 g scale.