✍ Scribed by de la Moya Cerero, Santiago ;Böhme, Marc ;Nieger, Martin ;Vögtle, Fritz
No coin nor oath required. For personal study only.
Hydrogen‐donor and hydrogen‐acceptor substituted chiral cyclophanes with a 2benzeno2pyridinophane 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.
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Chiral supermolecules may be obtained from suitable achiral molecular constituents associated through a dissymmetrizing interaction mode. This is the case for the supermolecules I-IV formed by hydrogen-bonding association between the achiral complementary components la, b and Za,b,c. The crystal str