Supramolecular Properties of a Monocarboxylic Acid-Functionalized "Texas-Sized" Molecular Box

Journal of the American Chemical Society
Ren-Tsung WuJonathan L Sessler

Abstract

A new carboxylic acid-functionalized "Texas-sized" molecular box TxSB-CO2H has been prepared by combining two separate building blocks via an iodide-catalyzed macrocyclization reaction. A single-crystal X-ray diffraction analysis revealed a paired "clip-like" dimer in the solid state. Concentration-dependent behavior is seen for samples of TxSB-CO2H as prepared, as inferred from 1H NMR spectroscopic studies carried out in DMSO- d6. However, in the presence of excess acid (1% by weight of deuterated trifluoracetic acid; TFA- d1), little evidence of aggregation is seen in DMSO- d6 except at the highest accessible concentrations. In contrast, the conjugate base form, TxSB-CO2-, produced in situ via the addition of excess triethylamine to DMSO- d6 solutions of TxSB-CO2H acts as a self-complementary monomer that undergoes self-assembly to stabilize a formal oligomer ([TxSB-CO2-] n) with a degree of polymerization of approximately 5-6 at a concentration of 70 mM. Evidence in support of the proposed oligomerization of TxSB-CO2- in solution and in the solid state came from one- and two-dimensional 1H NMR spectroscopy, X-ray crystallography, dynamic light scattering (DLS), and scanning electron microscopy (SEM). A series of solution-bas...Continue Reading

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Citations

Aug 23, 2018·Proceedings of the National Academy of Sciences of the United States of America·Chao SunWilliam R Dichtel
May 1, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Xiaodong ChiJonathan L Sessler
Apr 9, 2019·Journal of the American Chemical Society·Xiaodong ChiJonathan L Sessler
Jun 12, 2019·Accounts of Chemical Research·Xiaofan JiJonathan L Sessler
Nov 3, 2021·Chemical Communications : Chem Comm·Qiang ShiLeyong Wang

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