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  Stereochemistry of bistricyclic aromatic enes and related polycyclic systems

Biedermann, P. U., & Agranat, I. (2014). Stereochemistry of bistricyclic aromatic enes and related polycyclic systems. Topics in Current Chemistry, 350, 177-277. doi:10.1007/128_2014_534.

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Item Permalink: http://hdl.handle.net/11858/00-001M-0000-0026-B4F8-E Version Permalink: http://hdl.handle.net/11858/00-001M-0000-002C-E050-B
Genre: Journal Article

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 Creators:
Biedermann, Paul Ulrich1, 2, Author              
Agranat, Israel2, Author              
Affiliations:
1Atomistic Modelling, Interface Chemistry and Surface Engineering, Max-Planck-Institut für Eisenforschung GmbH, Max Planck Society, ou_1863350              
2Organic Chemistry, Institute of Chemistry, The Hebrew University of Jerusalem, Philadelphia Bldg. #201-205, Edmond J. Safra Campus, Jerusalem, Israel, ou_persistent22              

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 Abstract: Bistricyclic aromatic enes (BAEs) and related polycyclic systems are a class of molecular materials that display a rich variety of conformations, dynamic stereochemistry and switchable chirality, color, and spectroscopic properties. This is due to the a subtle interplay of the inherent preference for planarity of aromatic systems and the competing necessity of non-planarity due to intramolecular overcrowding in the fjord regions built into the general molecular structure of BAEs. The conformational, dynamic, and spectroscopic properties may be designed and fine-tuned, e.g., by variation of the bridging groups X and Y, the overcrowding in the fjord regions, extensions of the aromatic system, or other modifications of the general BAE structure, based on the fundamental understanding of the structure-property relationships (SPR). The present review provides an analysis of the conformational spaces and the dynamic stereochemistry of overcrowded bistricyclic aromatic enes applying fundamental symmetry considerations. The symmetry analysis presented here allows deeper insight into the conformations, chirality, and the mechanisms of the dynamic stereochemistry, and will be instrumental in future computational studies.

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Language(s): eng - English
 Dates: 2014-07-09
 Publication Status: Published in print
 Pages: 101
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: ISI: 25005068
DOI: 10.1007/128_2014_534
 Degree: -

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Title: Topics in Current Chemistry
  Abbreviation : Top. Curr. Chem.
Source Genre: Journal
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Publ. Info: Berlin : Springer-Verlag
Pages: - Volume / Issue: 350 Sequence Number: - Start / End Page: 177 - 277 Identifier: ISSN: 0340-1022
CoNE: https://pure.mpg.de/cone/journals/resource/110992357266830