Easier to Twist than Bend: The Scope of the Bridge Formation Approach to Naphthalenophane Synthesis

Anjan Bedi*, Linda J.W. Shimon, Benny Bogoslavsky, Ori Gidron*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

Twisting anthracene and higher acenes can alter their optical, magnetic, and electronic properties. To test the effect of twisting on the lower homologue, naphthalene, we synthesized tethered naphthalenophanes bearing alkyl bridges. Both X-ray structure and DFT calculations show that hexyl and butyl bridges induce a 6° and 12° end-to-end twist on the naphthalene unit, respectively. Attempts to increase the twisting further using shorter tethers resulted in an elimination product. Enantiomerically pure naphthalenophanes display strong chiroptical properties, which intensify with increasing twist. Attempts to induce bending, rather than twisting, using the same synthetic methodology, resulted in intermolecular dimerization, yielding macrocyclic naphthalenes. This work highlights the importance of steric hindrance in the synthesis of curved cyclophanes using the bridge formation approach.

Original languageAmerican English
Pages (from-to)323-329
Number of pages7
JournalOrganic Materials
Volume2
Issue number4
DOIs
StatePublished - 8 Sep 2020

Bibliographical note

Publisher Copyright:
© 2020 Georg Thieme Verlag. All rights reserved.

Keywords

  • acenes
  • chirality
  • curved aromatic molecules
  • cyclophanes

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