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Title: UO22+-mediated ring contraction of pyrihexaphyrin: synthesis of a contracted expanded porphyrin-uranyl complex

Abstract

A new mixed hexaphyrin, pyrihexaphyrin (0.1.0.0.1.0) (1), was prepared via an acid catalyzed cyclization between 5,5'-(pyridine-2,6-diyl)bis(pyrrole-2-carbaldehyde) (2) and terpyrrole (3). This expanded porphyrin undergoes a ring contraction upon metallation with uranyl silylamide [UO2[N(SiMe3)2]2] under anaerobic conditions followed by purification over basic aluminum oxide exposed to air. The uranyl-contracted pyrihexaphyrin (0.0.0.0.1.0) complex (4) produced as a result contains a unique structural architecture and possesses a formally 22 π-electron globally aromatic periphery, as inferred from NMR spectroscopy, single crystal X-ray diffraction, and computational analyses. Support for the proposed contraction mechanism came from experimental data and DFT calculations. Proton NMR and mass spectroscopic analysis provided the first insight into expanded porphyrin-mediated activation of the uranyl dication (UO22+).

Authors:
ORCiD logo [1]; ORCiD logo [1]; ORCiD logo [1];  [1]; ORCiD logo [1]; ORCiD logo [1];  [1]; ORCiD logo [1]
  1. Univ. of Texas, Austin, TX (United States)
Publication Date:
Research Org.:
Univ. of Texas, Austin, TX (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES); Robert A. Welch Foundation; National Institutes of Health (NIH)
OSTI Identifier:
1598883
Grant/Contract Number:  
FG02-01ER15186; F-0018; 1-S10-OD021508-01
Resource Type:
Accepted Manuscript
Journal Name:
Chemical Science
Additional Journal Information:
Journal Volume: 10; Journal Issue: 21; Journal ID: ISSN 2041-6520
Publisher:
Royal Society of Chemistry
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Brewster, James T., Root, Harrison D., Mangel, Daniel, Samia, Adam, Zafar, Hadiqa, Sedgwick, Adam C., Lynch, Vincent M., and Sessler, Jonathan L. UO22+-mediated ring contraction of pyrihexaphyrin: synthesis of a contracted expanded porphyrin-uranyl complex. United States: N. p., 2019. Web. doi:10.1039/C9SC01593K.
Brewster, James T., Root, Harrison D., Mangel, Daniel, Samia, Adam, Zafar, Hadiqa, Sedgwick, Adam C., Lynch, Vincent M., & Sessler, Jonathan L. UO22+-mediated ring contraction of pyrihexaphyrin: synthesis of a contracted expanded porphyrin-uranyl complex. United States. https://doi.org/10.1039/C9SC01593K
Brewster, James T., Root, Harrison D., Mangel, Daniel, Samia, Adam, Zafar, Hadiqa, Sedgwick, Adam C., Lynch, Vincent M., and Sessler, Jonathan L. Tue . "UO22+-mediated ring contraction of pyrihexaphyrin: synthesis of a contracted expanded porphyrin-uranyl complex". United States. https://doi.org/10.1039/C9SC01593K. https://www.osti.gov/servlets/purl/1598883.
@article{osti_1598883,
title = {UO22+-mediated ring contraction of pyrihexaphyrin: synthesis of a contracted expanded porphyrin-uranyl complex},
author = {Brewster, James T. and Root, Harrison D. and Mangel, Daniel and Samia, Adam and Zafar, Hadiqa and Sedgwick, Adam C. and Lynch, Vincent M. and Sessler, Jonathan L.},
abstractNote = {A new mixed hexaphyrin, pyrihexaphyrin (0.1.0.0.1.0) (1), was prepared via an acid catalyzed cyclization between 5,5'-(pyridine-2,6-diyl)bis(pyrrole-2-carbaldehyde) (2) and terpyrrole (3). This expanded porphyrin undergoes a ring contraction upon metallation with uranyl silylamide [UO2[N(SiMe3)2]2] under anaerobic conditions followed by purification over basic aluminum oxide exposed to air. The uranyl-contracted pyrihexaphyrin (0.0.0.0.1.0) complex (4) produced as a result contains a unique structural architecture and possesses a formally 22 π-electron globally aromatic periphery, as inferred from NMR spectroscopy, single crystal X-ray diffraction, and computational analyses. Support for the proposed contraction mechanism came from experimental data and DFT calculations. Proton NMR and mass spectroscopic analysis provided the first insight into expanded porphyrin-mediated activation of the uranyl dication (UO22+).},
doi = {10.1039/C9SC01593K},
journal = {Chemical Science},
number = 21,
volume = 10,
place = {United States},
year = {Tue Apr 30 00:00:00 EDT 2019},
month = {Tue Apr 30 00:00:00 EDT 2019}
}

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