Helquats: A facile, modular, scalable route to novel helical dications

Adriaenssens, L.a and Severa, L.a and Šálová, T.a and Císa�ová, I.b and Pohl, R.a and Šaman, D.a and Rocha, S.V.c and Finney, N.S.c and Pospíšil, L.a and Slaví�ek, P.d and Teplý, F.a (2009) Helquats: A facile, modular, scalable route to novel helical dications. Chemistry - A European Journal, 15 (5). pp. 1072-1076. ISSN 09476539

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Abstract

The synthesis and properties of helical extended diquat (helquat), and derivatives that bear resemblance to diquat and azoniahelicene, was reported. Triyne with elongated tethers connecting the heterocyclic moiety with the pendant alkyne functionalities undergoing cycloisomerization give helquat featuring two seven-membered rings. The seven helquats reported are accessed uniformly in three steps from commercially available starting materials, entailing a Sonogashira coupling, bisquaternization, cycloisomerization, and 2+2+2 cycloisomerization. The evidence for the reversible electrochemical Weiz-type manifold and regular columnar stacks in crystal structures suggest the potential of helquats as electroactive functional elements.

Additional Information:cited By 63 The final published version of this article can be accessed online at https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.200801904 Copyright © 2009 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim
Keywords:Acetylene, Positive ions, Air-tolerant cycloisomerization, Dications, Diquat, Helical structures, Heteroaromatic cations, Sonogashira coupling, Electrochemistry
Subjects:F Physical Sciences > F100 Chemistry
Divisions:College of Science > School of Chemistry
ID Code:22745
Deposited On:25 Jul 2018 10:45

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