Synthesis, x-ray structure, and properties of a tetrabenzannelated 1,2,4,5-cyclophane

Michael Brettreich, Michael Bendikov, Sterling Chaffins, Dmitrii F. Perepichka, Olivier Dautel, Hieu Duong, Roger Helgeson, Fred Wudl

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

Highly strained but thermally stable: Tetrabenzocyclophane 1, which was obtained in a four-step synthesis by two Diels - Alder addition reactions (see scheme) sublimes at high temperature, rather than decomposing. The distorted aromatic rings are more reactive with tetracyanoethylene than those in [2.2]paracyclophane. Another consequence of heightened strain is a bathochromic shift of the cyclophane band to 330 nm, the longest wavelength absorption for this band to date.

Original languageEnglish
Pages (from-to)3688-3691
Number of pages4
JournalAngewandte Chemie - International Edition
Volume41
Issue number19
DOIs
Publication statusPublished - Oct 4 2002

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Addition reactions
X rays
Wavelength
Temperature
tetracyanoethylene
(2.2)paracyclophane

Keywords

  • Cycloaddition
  • Cyclophanes
  • Density functional calculations
  • Electrochemistry
  • Strained molecules

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Synthesis, x-ray structure, and properties of a tetrabenzannelated 1,2,4,5-cyclophane. / Brettreich, Michael; Bendikov, Michael; Chaffins, Sterling; Perepichka, Dmitrii F.; Dautel, Olivier; Duong, Hieu; Helgeson, Roger; Wudl, Fred.

In: Angewandte Chemie - International Edition, Vol. 41, No. 19, 04.10.2002, p. 3688-3691.

Research output: Contribution to journalArticle

Brettreich, Michael ; Bendikov, Michael ; Chaffins, Sterling ; Perepichka, Dmitrii F. ; Dautel, Olivier ; Duong, Hieu ; Helgeson, Roger ; Wudl, Fred. / Synthesis, x-ray structure, and properties of a tetrabenzannelated 1,2,4,5-cyclophane. In: Angewandte Chemie - International Edition. 2002 ; Vol. 41, No. 19. pp. 3688-3691.
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