A hybrid macrocycle with a pyridine subunit displays aromatic character upon uranyl cation complexation

I. Ting Ho; Zhan Zhang; Masatoshi Ishida; Vincent M. Lynch; Won Young Cha; Young Mo Sung; Dongho Kim; Jonathan L. Sessler

doi:10.1021/ja412520g

A hybrid macrocycle with a pyridine subunit displays aromatic character upon uranyl cation complexation

I. Ting Ho, Zhan Zhang, Masatoshi Ishida, Vincent M. Lynch, Won Young Cha, Young Mo Sung, Dongho Kim, Jonathan L. Sessler

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

39 Citations (Scopus)

Abstract

Reported here is a new hybrid macrocycle, cyclo[1]furan[1]pyridine[4] pyrrole (1), that bears analogy to the previously reported mixed heterocycle system cyclo[2]pyridine[4]pyrrole (2) and cyclo[6]pyrrole 3, an all-pyrrole 22 π-electron aromatic expanded porphyrin. The oxidized, dianionic form of 1, [1 - 4H]^2-, has been characterized as its uranyl complex. In contrast to 2 and 3 and in spite of the presence of a 2,6-disubstituted pyridine subunit, the uranyl complex of [1 - 4H]^2- displays solid-state structural and solution-phase spectroscopic features consistent with contributions to the overall electronic structure that involve a conjugated, (4n + 2) π-electron aromatic periphery.

Original language	English
Pages (from-to)	4281-4286
Number of pages	6
Journal	Journal of the American Chemical Society
Volume	136
Issue number	11
DOIs	https://doi.org/10.1021/ja412520g
Publication status	Published - 2014 Mar 19

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja412520g

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title = "A hybrid macrocycle with a pyridine subunit displays aromatic character upon uranyl cation complexation",

abstract = "Reported here is a new hybrid macrocycle, cyclo[1]furan[1]pyridine[4] pyrrole (1), that bears analogy to the previously reported mixed heterocycle system cyclo[2]pyridine[4]pyrrole (2) and cyclo[6]pyrrole 3, an all-pyrrole 22 π-electron aromatic expanded porphyrin. The oxidized, dianionic form of 1, [1 - 4H]2-, has been characterized as its uranyl complex. In contrast to 2 and 3 and in spite of the presence of a 2,6-disubstituted pyridine subunit, the uranyl complex of [1 - 4H]2- displays solid-state structural and solution-phase spectroscopic features consistent with contributions to the overall electronic structure that involve a conjugated, (4n + 2) π-electron aromatic periphery.",

author = "Ho, {I. Ting} and Zhan Zhang and Masatoshi Ishida and Lynch, {Vincent M.} and Cha, {Won Young} and Sung, {Young Mo} and Dongho Kim and Sessler, {Jonathan L.}",

year = "2014",

month = mar,

day = "19",

doi = "10.1021/ja412520g",

language = "English",

volume = "136",

pages = "4281--4286",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

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A hybrid macrocycle with a pyridine subunit displays aromatic character upon uranyl cation complexation. / Ho, I. Ting; Zhang, Zhan; Ishida, Masatoshi; Lynch, Vincent M.; Cha, Won Young; Sung, Young Mo; Kim, Dongho; Sessler, Jonathan L.

In: Journal of the American Chemical Society, Vol. 136, No. 11, 19.03.2014, p. 4281-4286.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - A hybrid macrocycle with a pyridine subunit displays aromatic character upon uranyl cation complexation

AU - Ho, I. Ting

AU - Zhang, Zhan

AU - Ishida, Masatoshi

AU - Lynch, Vincent M.

AU - Cha, Won Young

AU - Sung, Young Mo

AU - Kim, Dongho

AU - Sessler, Jonathan L.

PY - 2014/3/19

Y1 - 2014/3/19

N2 - Reported here is a new hybrid macrocycle, cyclo[1]furan[1]pyridine[4] pyrrole (1), that bears analogy to the previously reported mixed heterocycle system cyclo[2]pyridine[4]pyrrole (2) and cyclo[6]pyrrole 3, an all-pyrrole 22 π-electron aromatic expanded porphyrin. The oxidized, dianionic form of 1, [1 - 4H]2-, has been characterized as its uranyl complex. In contrast to 2 and 3 and in spite of the presence of a 2,6-disubstituted pyridine subunit, the uranyl complex of [1 - 4H]2- displays solid-state structural and solution-phase spectroscopic features consistent with contributions to the overall electronic structure that involve a conjugated, (4n + 2) π-electron aromatic periphery.

AB - Reported here is a new hybrid macrocycle, cyclo[1]furan[1]pyridine[4] pyrrole (1), that bears analogy to the previously reported mixed heterocycle system cyclo[2]pyridine[4]pyrrole (2) and cyclo[6]pyrrole 3, an all-pyrrole 22 π-electron aromatic expanded porphyrin. The oxidized, dianionic form of 1, [1 - 4H]2-, has been characterized as its uranyl complex. In contrast to 2 and 3 and in spite of the presence of a 2,6-disubstituted pyridine subunit, the uranyl complex of [1 - 4H]2- displays solid-state structural and solution-phase spectroscopic features consistent with contributions to the overall electronic structure that involve a conjugated, (4n + 2) π-electron aromatic periphery.

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A hybrid macrocycle with a pyridine subunit displays aromatic character upon uranyl cation complexation

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