ISSN:
0947-6539
Keywords:
cyclophanes
;
macrocyclisations
;
molecular ribbons
;
nanostructures
;
repetitive syntheses
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The longest molecular ribbons known to date (3-10), composed of a series of [3.3]metacyclophane units, have been synthesised by means of a repetitive synthetic strategy. These multiple ring systems with up to nine bridged benzene rings in a row are the longest structurally perfect cyclophane sequences known to date. The synthetic strategy comprises three steps: ester reduction to a tetrakis(hydroxymethyl) compound, derivatisation to the corresponding tetrakis(bromomethyl) derivative, and double cyclisation with the new key building block 14, which was especially developed for this sequence. Single-crystal X-ray analyses (3 a-7 a) and 1H NMR spectroscopy (3-10) show that, regardless of their length, these molecules adopt zigzag folded all-syn conformations. π-Stacks of nanometre dimensions are thus formed.
Additional Material:
3 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/chem.1460020714
