1‐(Methylamino)anthracene – An Accessible Building Block for Photoresponsive Compounds. Issue 47 (16th November 2018)

• Record Type: Journal Article
• Authors: Ulatowski, Filip; Melaniuk, Karolina
• Other Names: Gryko Daniel T. guestEditor.
• Is Part Of: European journal of organic chemistry. Issue 47(2018)
• Page Start: 6629
• Page End: 6633
• Publication Date: 2018-11-16
• Subjects: Photochemistry -- Cycloaddition -- Supramolecular chemistry -- Anthracene dimerization -- Anion receptors; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201800897
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : In this paper we present a convenient and scalable synthesis of 1‐(methylamino)anthracene, which is a potent building block for the construction of photoresponsive materials. With this structural motif we have synthesized an anion receptor bearing two anthracene groups. Interaction of a chloride anion with the anthracene moieties increases the association constant. Photocycloaddition allows to obtain a single macrocyclic receptor, which exhibits higher binding constants due to the macrocyclic effect. Abstract : Facile synthesis provides a novel anthracene‐based amine, which acts as a versatile building block for the construction of photoswitchable receptors. Incorporation of this structural motif into dipicolinic amide provides a photoresponsive anion receptor. Upon irradiation with 360 nm light, cycloaddition occurs to yield macrocyclic receptors with higher affinities for anions.