A photoswitchable rotaxane with a folded molecular thread

Chemistry : a European Journal
Werner AbrahamKarin Buck

Abstract

Novel [2]rotaxanes containing the tetracationic cyclophane cyclobis(paraquat-4,4-biphenylene) and a dumbbell-shaped molecular thread incorporating a photoactive diarylcycloheptatriene station as well as a photoinactive anisol station have been synthesized with yields of nearly 50 % by the alkylative endcapping method. The rotaxane was transformed into the related rotaxane incorporating a diaryl tropylium unit by electrochemical oxidation. The precursor of the cycloheptatrienyl rotaxane, the related pseudorotaxane, and the rotaxanes incorporating the diarylcycloheptatriene and the corresponding tropylium unit were characterized by (1)HNMR spectroscopy and UV/Vis spectroscopy. According to the NMR spectra, both the cycloheptatriene and the tropylium rotaxane possess a folded conformation enabling the tetracationic cyclophane to interact with two stations. The diarylcycloheptatriene station is incorporated inside the cavity of the cyclophane and the anisol station resides alongside the bipyridinium unit of the cyclophane. In contrast, the anisol station is inside the cyclophane in the tropylium rotaxane. The exchange between both conformations can be achieved by introducing the methoxy leaving group into the cycloheptatriene ring;...Continue Reading

Citations

Sep 9, 2015·Chemical Reviews·Sundus Erbas-CakmakAlina L Nussbaumer
Nov 8, 2018·Dalton Transactions : an International Journal of Inorganic Chemistry·Philipp LangerNeil R Champness
May 27, 2006·Organic & Biomolecular Chemistry·Shaun P GaynorRonald N Warrener
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Nov 30, 2006·Angewandte Chemie·Euan R KayFrancesco Zerbetto
Aug 24, 2010·Organic & Biomolecular Chemistry·Antje Vetter, Werner Abraham
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Mar 28, 2006·Chemical Society Reviews·He Tian, Qiao-Chun Wang
Jul 23, 2014·Organic & Biomolecular Chemistry·Ziyong LiJun Yin
Dec 17, 2008·Organic & Biomolecular Chemistry·Werner AbrahamSabine Jacob
Apr 9, 2008·The Journal of Organic Chemistry·Kathleen M Mullen, Maxwell J Gunter
Jun 28, 2008·Chemical Reviews·Konrad Szaciłowski
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