Towards the synthesis of Molecular Tweezers

  • Xingjun Zhou

Student thesis: Master of Science by Research


There is much current interest in the development of sensors for the detection of high energy volatile organics in the atmosphere and organic pollutants.1 This thesis describes initial efforts directed towards the synthesis of molecular tweezers which are based on anthraquinone as a robust and readily available scaffold. The synthesis of 1,8-diiodoanthraquinone is described and its conversion into 1,8-diphenylanthraquinone, 1,8-di(2-t-butylpyren-7-yl)anthraquinone, 1,8-di(pyren-1-yl)anthraquinone and 1,8-bis(phenylethynyl)anthracene-9,10-dione using Suzuki or Sonogashira cross-coupling reactions is presented. A competing oxidative coupling reaction of 2-(7-(t-butyl)pyren-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, leading to 7,7′-di-t-butyl-2,2′-bipyrene is also observed during the synthesis of 1,8-di(pyren-1-yl)anthraquinone. We conclude that the Suzuki reactions of 1,8-diodoanthraquinone are generally low-yielding and often generate complex reaction mixtures that are difficult to purify. In comparison the Sonogashira reaction between 1,8-diiodoanthraquinone and phenylacetylene appear to be much cleaner and afford the desired, cross coupled product, in acceptable yield. Future work will delineate the generality of the Sonogashira reactions of 1,8-diiodoanthraquinoine and investigate the interaction of these molecular tweezers with aromatic substrates.
Date of Award31 Dec 2020
Original languageEnglish
Awarding Institution
  • The University of Manchester
SupervisorPeter Quayle (Supervisor) & Stephen Yeates (Supervisor)


  • Molecular Tweezers

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