An excimer-based, binuclear, on-off switchable calix[4]crown chemosensor

Kuk Kim Sung, Ho Lee Seoung, Yeon Lee Ji, Yong Lee Jin, Richard A. Bartsch, Jong Seung Kim

Research output: Contribution to journalArticle

35 Citations (Scopus)

Abstract

A new fluorescent chemosensor with two different types of cation binding sites on the lower rims of a 1,3-alternate calix[4]arene (1) is synthesized. Two pyrene moieties linked to a cation recognition unit composed of two amide groups form a strong excimer in solution. For 1, the excimer fluorescence is quenched by Pb2+, but revived by addition of K+ to the Pb2+ ligand complex. Thus, metal ion exchange produces an on-off switchable, fluorescent chemosensor. Computational results show that the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbitals (LUMO) of the two pyrene moieties interact under UV irradiation of 1 and its K+ complex, while such HOMO-LUMO interactions are absent in the Pb2+ complex.

Original languageEnglish
Pages (from-to)16499-16506
Number of pages8
JournalJournal of the American Chemical Society
Volume126
Issue number50
DOIs
Publication statusPublished - 2004 Dec 22
Externally publishedYes

Fingerprint

Molecular orbitals
Crowns
Cations
Ion Exchange
Pyrene
Amides
Fluorescence
Positive ions
Metals
Binding Sites
Ligands
Binding sites
Metal ions
Ion exchange
Irradiation
pyrene
calix(4)arene
rim 1

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

An excimer-based, binuclear, on-off switchable calix[4]crown chemosensor. / Sung, Kuk Kim; Seoung, Ho Lee; Ji, Yeon Lee; Jin, Yong Lee; Bartsch, Richard A.; Kim, Jong Seung.

In: Journal of the American Chemical Society, Vol. 126, No. 50, 22.12.2004, p. 16499-16506.

Research output: Contribution to journalArticle

Sung, Kuk Kim ; Seoung, Ho Lee ; Ji, Yeon Lee ; Jin, Yong Lee ; Bartsch, Richard A. ; Kim, Jong Seung. / An excimer-based, binuclear, on-off switchable calix[4]crown chemosensor. In: Journal of the American Chemical Society. 2004 ; Vol. 126, No. 50. pp. 16499-16506.
@article{1754308fd4d842d68e73e807c6b87f28,
title = "An excimer-based, binuclear, on-off switchable calix[4]crown chemosensor",
abstract = "A new fluorescent chemosensor with two different types of cation binding sites on the lower rims of a 1,3-alternate calix[4]arene (1) is synthesized. Two pyrene moieties linked to a cation recognition unit composed of two amide groups form a strong excimer in solution. For 1, the excimer fluorescence is quenched by Pb2+, but revived by addition of K+ to the Pb2+ ligand complex. Thus, metal ion exchange produces an on-off switchable, fluorescent chemosensor. Computational results show that the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbitals (LUMO) of the two pyrene moieties interact under UV irradiation of 1 and its K+ complex, while such HOMO-LUMO interactions are absent in the Pb2+ complex.",
author = "Sung, {Kuk Kim} and Seoung, {Ho Lee} and Ji, {Yeon Lee} and Jin, {Yong Lee} and Bartsch, {Richard A.} and Kim, {Jong Seung}",
year = "2004",
month = "12",
day = "22",
doi = "10.1021/ja045689c",
language = "English",
volume = "126",
pages = "16499--16506",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "American Chemical Society",
number = "50",

}

TY - JOUR

T1 - An excimer-based, binuclear, on-off switchable calix[4]crown chemosensor

AU - Sung, Kuk Kim

AU - Seoung, Ho Lee

AU - Ji, Yeon Lee

AU - Jin, Yong Lee

AU - Bartsch, Richard A.

AU - Kim, Jong Seung

PY - 2004/12/22

Y1 - 2004/12/22

N2 - A new fluorescent chemosensor with two different types of cation binding sites on the lower rims of a 1,3-alternate calix[4]arene (1) is synthesized. Two pyrene moieties linked to a cation recognition unit composed of two amide groups form a strong excimer in solution. For 1, the excimer fluorescence is quenched by Pb2+, but revived by addition of K+ to the Pb2+ ligand complex. Thus, metal ion exchange produces an on-off switchable, fluorescent chemosensor. Computational results show that the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbitals (LUMO) of the two pyrene moieties interact under UV irradiation of 1 and its K+ complex, while such HOMO-LUMO interactions are absent in the Pb2+ complex.

AB - A new fluorescent chemosensor with two different types of cation binding sites on the lower rims of a 1,3-alternate calix[4]arene (1) is synthesized. Two pyrene moieties linked to a cation recognition unit composed of two amide groups form a strong excimer in solution. For 1, the excimer fluorescence is quenched by Pb2+, but revived by addition of K+ to the Pb2+ ligand complex. Thus, metal ion exchange produces an on-off switchable, fluorescent chemosensor. Computational results show that the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbitals (LUMO) of the two pyrene moieties interact under UV irradiation of 1 and its K+ complex, while such HOMO-LUMO interactions are absent in the Pb2+ complex.

UR - http://www.scopus.com/inward/record.url?scp=11444261400&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=11444261400&partnerID=8YFLogxK

U2 - 10.1021/ja045689c

DO - 10.1021/ja045689c

M3 - Article

C2 - 15600353

AN - SCOPUS:11444261400

VL - 126

SP - 16499

EP - 16506

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 50

ER -