Pyrrole- and Naphthobipyrrole-Strapped Calix[4]pyrroles as Azide Anion Receptors

Kim, Seung Hyeon; Lee, Juhoon; Vargas-Zúñiga, Gabriela I.; Lynch, Vincent M.; Hay, Benjamin P.; Sessler, Jonathan L.; Kim, Sung Kuk

doi:10.1021/acs.joc.7b03135

Pyrrole- and Naphthobipyrrole-Strapped Calix[4]pyrroles as Azide Anion Receptors

Journal Article · Tue Feb 13 23:00:00 EST 2018 · Journal of Organic Chemistry

DOI:https://doi.org/10.1021/acs.joc.7b03135· OSTI ID:1480249

Kim, Seung Hyeon ^[1]; Lee, Juhoon ^[2]; Vargas-Zúñiga, Gabriela I. ^[2]; Lynch, Vincent M. ^[2]; Hay, Benjamin P. ^[3]; ^[2]; ^[1]

Gyeongsang National Univ., Jinju (Korea)
Univ. of Texas, Austin, TX (United States)
Supramolecular Design Inst., Oak Ridge, TN (United States)

Here, the binding interactions between the azide anion (N₃^–) and the strapped calix[4]pyrroles 2 and 3 bearing auxiliary hydrogen bonding donors on the bridging moieties, as well as of normal calix[4]pyrrole 1, were investigated via ¹H NMR spectroscopic and isothermal titration calorimetry analyses. The resulting data revealed that receptors 2 and 3 have significantly higher affinities for the azide anion in organic media as compared with the unfunctionalized calix[4]pyrrole 1 and other azide receptors reported to date. Single crystal X-ray diffraction analyses and calculations using density functional theory revealed that receptor 2 binds CsN₃ in two distinct structural forms. As judged from the metric parameters, in the resulting complexes one limiting azide anion resonance contributor is favored over the other, with the specifics depending on the binding mode. In contrast to what is seen for 2, receptor 3 forms a CsN₃ complex in 20% CD₃OD in CDCl₃, wherein the azide anion is bound only vertically to the NH protons of the calix[4]pyrrole and the cesium cation is complexed within the cone shaped-calix[4]pyrrole bowl. The bound cesium cation is also in close proximity to a naphthobipyrrole subunit present in a different molecule, forming an apparent cation-π complex.

View Accepted Manuscript (DOE)

Research Organization:: Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States). National Energy Research Scientific Computing Center (NERSC)

Sponsoring Organization:: USDOE Office of Science (SC); National Research Foundation (NRF); National Institutes of Health (NIH); Robert A. Welch Foundation

Grant/Contract Number:: AC02-05CH11231

OSTI ID:: 1480249

Journal Information:: Journal of Organic Chemistry, Journal Name: Journal of Organic Chemistry Journal Issue: 5 Vol. 83; ISSN 0022-3263

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

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Strapped calix[4]pyrroles: from syntheses to applications Peng, Sangshan; He, Qing; Vargas-Zúñiga, Gabriela I. Chemical Society Reviews, Vol. 49, Issue 3 https://doi.org/10.1039/c9cs00528e	journal	January 2020
Cesium halide ion pair recognition by a pyrrole strapped Calix[4]pyrrole Yang, Ju Ho; Lynch, Vincent M.; Sessler, Jonathan L. Supramolecular Chemistry, Vol. 31, Issue 3 https://doi.org/10.1080/10610278.2018.1535711	journal	October 2018

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Anions
Azides
Binding modes
Crystal structure
Receptors

CCDC 1586342: Experimental Crystal Structure Determination Kim, Seung Hyeon; Lee, Juhoon; Vargas-Zúñiga, Gabriela I. https://doi.org/10.5517/ccdc.csd.cc1q7qb0 The current record is supplemented by this dataset	dataset	January 2018
CCDC 1586343: Experimental Crystal Structure Determination Kim, Seung Hyeon; Lee, Juhoon; Vargas-Zúñiga, Gabriela I. https://doi.org/10.5517/ccdc.csd.cc1q7qc1 The current record is supplemented by this dataset	dataset	January 2018
CCDC 1586344: Experimental Crystal Structure Determination Kim, Seung Hyeon; Lee, Juhoon; Vargas-Zúñiga, Gabriela I. https://doi.org/10.5517/ccdc.csd.cc1q7qd2 The current record is supplemented by this dataset	dataset	January 2018

Pyrrole- and Naphthobipyrrole-Strapped Calix[4]pyrroles as Azide Anion Receptors

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