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Chiral Pyridinophanes as Hydrogen‐Bonding Supramolecular Building Blocks
Author(s) -
de la Moya Cerero Santiago,
Böhme Marc,
Nieger Martin,
Vögtle Fritz
Publication year - 1997
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199719970626
Subject(s) - supramolecular chemistry , chemistry , hydrogen bond , circular dichroism , crystallography , molecule , acceptor , melamine , cyclophane , stereochemistry , crystal structure , organic chemistry , physics , condensed matter physics
Hydrogen‐donor and hydrogen‐acceptor substituted chiral cyclophanes with a [2](1,3)benzeno[2](3,5)pyridinophane framework have been synthesized, enantiomerically separated, and analysed by circular dichroism (CD). X‐ray structure determination and CD analyses show that these cyclophanes are able to act as hydrogen‐bonding donor/acceptor building blocks for the design of chiral supramolecular aggregates with suitable complementary partners. Starting from the pyridinophane N ‐oxide 4 , selective reactions lead to the new chiral pyridinophanes 5–7 in high yields. The X‐ray structure analysis of the pyridinophane‐2‐carbonitrile 5 reveals a multilayered herringbone structure as it forms dimeric aggregates. The CD analysis of the host 7 with the complementary guest molecules melamine and cyanuric acid elucidates the formation of supramolecular complexes in solution.