Controlling the helical pitch of foldamers through terminal functionality: A solid state study
Davis, A.R. Ozturk, S. Male, L. Pike, S.J.
Davis, A.R.
Ozturk, S.
Male, L.
Pike, S.J.
Publication Date
2024-12
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© 2024 The Author(s). Chemistry - A European Journal published by Wiley-VCH GmbH
This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
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2024-09-09
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Abstract
Developing new methods to control the size and shape of the helical structures adopted by foldamers is highly important as the secondary structure displayed by these supramolecular scaffolds often dictates their activity and function. Herein, we report on a systematic study demonstrating that the helical pitch of ortho‐azobenzene/2,6‐pyridyldicarboxamide foldamers can be readily controlled through the nature of the terminal functionality. Remarkably, simply through varying the end group of the foldamer, and without modifying any other structural features of the scaffold, the helical pitch can be over doubled in magnitude (from 3.4 Å–7.3 Å). Additionally, crystallographic analysis of a library ten foldamers has identified general trends in the influence of a range of terminal functionalities, including carboxylbenzyl (Cbz), diphenylcarbamyl (N(Ph)2), ferrocene (Fc) and tert‐butyloxycarbonyl (Boc), in controlling the folding behaviour of these supramolecular scaffolds. These studies could prove useful in the future development of functional foldamers which adopt specific sizes and shapes. A crystallographic study into the influence of varying the terminal functionality on the helical pitch of a series of foldamers is reported. Herein, we show that through systematic modification of the terminal functionality in the foldamer, from carboxylbenzyl (Cbz), diphenylamide (N(Ph)2), ferrocene to tert‐butyloxycarbonyl (Boc) helical pitches between 3.4–7.3 Å can be readily accessed in these supramolecular scaffolds.
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Citation
Davis AR, Ozturk S, Seaton C et al (2024) Controlling the helical pitch of foldamers through terminal functionality: A solid state study. Chemistry - A European Journal. 30(68): e202402892.
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