Synthesis of substituted pyrenes by indirect methods
The pyrene nucleus is a valuable component for materials, supramolecular and biological chemistry, due to its photophysical/electronic properties and extended rigid structure. However, its exploitation is hindered by the limited range of methods and outcomes for the direct substitution of pyrene its...
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| Published in | Organic & biomolecular chemistry Vol. 12; no. 2; pp. 212 - 232 |
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| Main Authors | , , |
| Format | Journal Article |
| Language | English |
| Published |
England
14.01.2014
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| Online Access | Get full text |
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| Summary: | The pyrene nucleus is a valuable component for materials, supramolecular and biological chemistry, due to its photophysical/electronic properties and extended rigid structure. However, its exploitation is hindered by the limited range of methods and outcomes for the direct substitution of pyrene itself. In response to this problem, a variety of indirect methods have been developed for preparing pyrenes with less usual substitution patterns. Herein we review these approaches, covering methods which involve reduced pyrenes, transannular ring closures and cyclisations of biphenyl intermediates. We also showcase the diverse range of substituted pyrenes which have been reported in the literature, and can serve as building blocks for new molecular architectures.
Substituted pyrenes have many uses, but may not be available
via
direct reactions on the parent hydrocarbon. This review highlights alternative strategies giving access to pyrenes with a very wide range of substitution patterns. |
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| Bibliography: | Tony Davis gained a B.A. in Chemistry from Oxford University in 1977, then stayed for a D.Phil. under Dr G. H. Whitham and postdoctoral work with Prof. J. E. Baldwin. In 1981 he moved to the ETH Zürich as a Royal Society European Exchange Fellow working with Prof. A. Eschenmoser, then in 1982 was appointed Lecturer in Organic Chemistry at Trinity College, Dublin. In September 2000 he moved to the University of Bristol, where he is Professor of Supramolecular Chemistry in the School of Chemistry. His research interests include the supramolecular chemistry of carbohydrates and anions, and the study of steroid-based nanoporous crystals. Juan M. Casas-Solvas obtained his first degree in chemistry at the University of Almería in 2001, where he also completed a PhD on the electrochemical characterisation of supramolecular chemistry of cyclic oligosaccharides and carbohydrate-protein binding interactions, under the supervision of Prof. A. Vargas-Berenguel. In 2010 he moved to the University of Bristol as an IEF Marie Curie Fellow under the supervision of Prof. A. P. Davis, where he worked on the design and construction of synthetic lectins for the biomimetic recognition of carbohydrates. Since May 2012 he works at Prof. Vargas-Berenguel's group on the preparation of multifunctional nanocarriers for anticancer drugs based on β-cyclodextrin, dendrimers and gold nanoparticles. Joshua Howgego grew up in Ipswich, UK, and completed his first degree in chemistry at the University of Reading. From there he moved to the University of Bristol to study for a PhD focussing on the design and synthesis of biomimetic receptors for carbohydrates, under the supervision of Professor Anthony Davis. Upon completion of his PhD Joshua entered the field of science journalism and in 2013 was appointed deputy news and opinions editor at SciDev.Net, a website that provides news and analysis of science as practised and applied in the developing world. ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
| ISSN: | 1477-0520 1477-0539 |
| DOI: | 10.1039/c3ob41993b |