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Chem Asian J. 2014 Apr;9(4):1039-44. doi: 10.1002/asia.201301729. Epub 2014 Feb 19.

Tetrathiafulvalene-based macrocycles formed by radical cation dimerization: the role of intramolecular hydrogen bonding and solvent.

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  • 1Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433 (China), Fax: (+86) 21-6564-1740.


Compounds 1 a and 1 b were prepared by appending two tetrathiafulvalene (TTF) units to an aromatic amide segment that is driven by six or two intramolecular N-H⋅⋅⋅O hydrogen bonds to adopt a folded conformation. UV/Vis absorption experiments revealed that if the TTF units were oxidized to TTF(·+) radical cations, the two compounds could form a stable single molecular noncovalent macrocycle in less polar dichloromethane or dichloroethane or a bimolecular noncovalent macrocycle in a binary mixture of dichloromethane with a more polar solvent owing to remarkably enhanced dimerization of the TTF(·+) units. The stability of the (TTF(·+))2 dimer was evaluated through UV/Vis absorption, electron paramagnetic resonance, and cyclic voltammetry experiments and also by comparing the results with those of control compound 2. The results showed that introduction of the intramolecular hydrogen bonds played a crucial role in promoting the stability of the (TTF(·+))2 dimer and thus the noncovalent macrocyclization of the two backbones in both uni- and bimolecular manners.

© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.


foldamers; hydrogen bonds; macrocyclization; radical cation dimerization; solvent effects

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