title: Photoswitching Behavior of a Cyclohexene-Bridged versus a Cyclopentene-Bridged Dithienylethene System.
abstract: Photoswitching is an intriguing way of incorporating functionality into molecules or their subunits. Dithienylethene switches are particularly promising, but have so far mostly been studied with five-membered ring (cyclopentenyl) backbones. We aim at comparing the switching properties of backbones with five and six carbon atoms in the ring. A major advantage is that cyclohexenyl rings offer new options for chiral functionalization. A slight change in the reaction conditions of a McMurry ring closure reaction leads to the formation of dithienyl derivatives with a cyclohexene backbone in reasonable yield. Density functional theory calculations were carried out, demonstrating the similarity of both compounds. Experimental results confirm the theoretical outcomes.
authors.affiliation: Department of Chemistry, Institute for Inorganic and Applied Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, 20146 Hamburg (Germany).
authors.forename: Torben
authors.initials: T
authors.lastname: Steenbock
authors.affiliation: Department of Chemistry, Institute for Inorganic and Applied Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, 20146 Hamburg (Germany).
authors.forename: Alejandra
authors.initials: A
authors.lastname: Escribano
authors.affiliation: Department of Chemistry, Institute for Inorganic and Applied Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, 20146 Hamburg (Germany). carmen.herrmann@chemie.uni-hamburg.de.
authors.forename: Jürgen
authors.initials: J
authors.lastname: Heck
authors.affiliation: Department of Chemistry, Institute for Inorganic and Applied Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, 20146 Hamburg (Germany). heck@chemie.uni-hamburg.de.
authors.forename: Carmen
authors.initials: C
authors.lastname: Herrmann
keywords: UV/Vis spectroscopy; density functional calculations; molecular switches; photochemistry; photochromism