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DABCO as a dynamic hinge between cofacial porphyrin panels and its tumbling inside a supramolecular cavity.

Authors
  • Samanta, Soumen K
  • Samanta, Debabrata
  • Bats, Jan W
  • Schmittel, Michael
Type
Published Article
Journal
The Journal of Organic Chemistry
Publisher
American Chemical Society
Publication Date
Sep 16, 2011
Volume
76
Issue
18
Pages
7466–7473
Identifiers
DOI: 10.1021/jo201252q
PMID: 21863790
Source
Medline
License
Unknown

Abstract

The heteroleptic supramolecular double-decker porphyrin 1 was synthesized with DABCO as a guest between two cofacial porphyrin units as characterized by (1)H NMR and ESI-MS. While DABCO is not seen to tumble inside the cavity, even at higher temperatures (80 °C), such motion was triggered upon addition of various coordinating ligands (quinuclidine, 4-bromopyridine, or excess of DABCO). Different stoichiometric amounts were needed depending on the n donor quality of the added ligands to initiate tumbling of the "inside" DABCO. As demonstrated in an example with excess DABCO, the tumbling was stopped by lowering the temperature to -50 °C.

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