Complementary Binding in Urea-Based Self-Folding Cavitands

Lledó, Agustí

doi:10.1021/acs.orglett.5b01747

Org. Lett.

2015

DOI: 10.1021/acs.orglett.5b01747

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Complementary Binding in Urea-Based Self-Folding Cavitands

Agustí Lledó

Abstract: A new family of cavitands bearing urea groups has been prepared. The hosts display a fluxional behavior akin to that of amide analogues. The ureido functions serve a dual role, stabilizing the folded conformer of the receptor and providing stabilization to guests present in the cavity.

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Cited by 3 publications

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Comprehensive Characterization of the Self‐Folding Cavitand Dynamics

López-Coll

Álvarez‐Yebra

Feixas

et al. 2021

Chemistry A European J

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The conformational equilibria and guest exchange process of a resorcin[4]arene derived self‐folding cavitand receptor have been characterized in detail by molecular dynamics simulations (MD) and 1H EXSY NMR experiments. A multi‐timescale strategy for exploring the fluxional behaviour of this system has been constructed, exploiting conventional MD and accelerated MD (aMD) techniques. The use of aMD allows the reconstruction of the folding/unfolding process of the receptor by sampling high‐energy barrier processes unattainable by conventional MD simulations. We obtained MD trajectories sampling events occurring at different timescales from ns to s: 1) rearrangement of the directional hydrogen bond seam stabilizing the receptor, 2) folding/unfolding of the structure transiting partially open intermediates, and 3) guest departure from different folding stages. Most remarkably, reweighing of the biased aMD simulations provided kinetic barriers that are in very good agreement with those determined experimentally by 1H NMR. These results constitute the first comprehensive characterization of the complex dynamic features of cavitand receptors. Our approach emerges as a valuable rational design tool for synthetic host‐guest systems

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Comprehensive Characterization of the Self‐Folding Cavitand Dynamics

López-Coll

Álvarez‐Yebra

Feixas

et al. 2021

Chemistry A European J

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Binding of ion pairs in a thiourea-functionalized self-folding cavitand

Lledó

Soler

2017

Org. Chem. Front.

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We report the synthesis of a new synthetic cavitand receptor with an embedded thiourea moiety directed at effective molecular recognition of ion pairs. Initial prospects towards the use of cavitands in biomimetic carbocationic cyclizations have been carried out, employing ionic guests as stable surrogates for putative substrates and intermediates. The cavitand displays tight binding with tetramethylammonium salts, with unforeseen slow exchange kinetics of both cation and anion componentsWe thank MINECO – Spanish Government (“Ramón y Cajal” grant to A. L. RYC2012-11112, CTQ2014-54306-P, and CTQ2014-61629-EXP), Generalitat de Catalunya, 2014SGR931, and Universitat de Girona (MPCUdG2016/096) for financial suppor

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A flexible self-folding receptor for coronene

et al. 2019

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Complementary Binding in Urea-Based Self-Folding Cavitands

Abstract: A new family of cavitands bearing urea groups has been prepared. The hosts display a fluxional behavior akin to that of amide analogues. The ureido functions serve a dual role, stabilizing the folded conformer of the receptor and providing stabilization to guests present in the cavity.

Cited by 3 publications

References 26 publications

Comprehensive Characterization of the Self‐Folding Cavitand Dynamics

Comprehensive Characterization of the Self‐Folding Cavitand Dynamics

Binding of ion pairs in a thiourea-functionalized self-folding cavitand

A flexible self-folding receptor for coronene

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