Self-assembly and characterization of a giant metallocycle

Hye Young Jang; Sung Youn Chang; Kyoung Jin Chang; Kyu Sung Jeong

doi:10.1016/j.tetlet.2005.02.048

Self-assembly and characterization of a giant metallocycle

Hye Young Jang, Sung Youn Chang, Kyoung Jin Chang, Kyu Sung Jeong

Department of Chemistry

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

3 Citations (Scopus)

Abstract

A giant, 100-membered metallocycle 3 was prepared via coordination bond-based self-assembly from W-shaped ligand 9 and a palladium complex. Metallocycle 3 may create three topologically discrete subcavities, thus capable of binding up to three molecules of a diamide guest by hydrogen-bonding interactions. Elemental analysis, ¹H NMR, and the ESI-mass spectra, and vapor pressure osmometry (VPO) data were all consistent with the structure of 3. N,N,N′,N′-tetramethylterephthalamide G was used as a guest for the binding study, and ESI-mass spectrum clearly displayed a characteristic, intense peak at m/z 1542 (41%), attributed to the fragment [3•G ₃-3CF₃SO₃]³⁺ of 1:3 (host/guest) complex. The ¹H NMR titration experiments gave association constants of 2300 ± 300 and 1200 ± 200 M^-1 in CDCl₃ at 25°C for two identical outer cavities, with weak positive cooperativity (Hill coefficient h = 1.3).

Original language	English
Pages (from-to)	2433-2436
Number of pages	4
Journal	Tetrahedron Letters
Volume	46
Issue number	14
DOIs	https://doi.org/10.1016/j.tetlet.2005.02.048
Publication status	Published - 2005 Apr 4

Bibliographical note

Funding Information:
This work was financially supported by the Korea Institute of the Center for Bioactive Molecular Hybrids (CBMH) and Science & Technology Evaluation and Planning (M10213030001- 02B1503-00310).

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tetlet.2005.02.048

Cite this

@article{47e58640d5564e4683cb10dc9c93e93f,

title = "Self-assembly and characterization of a giant metallocycle",

abstract = "A giant, 100-membered metallocycle 3 was prepared via coordination bond-based self-assembly from W-shaped ligand 9 and a palladium complex. Metallocycle 3 may create three topologically discrete subcavities, thus capable of binding up to three molecules of a diamide guest by hydrogen-bonding interactions. Elemental analysis, 1H NMR, and the ESI-mass spectra, and vapor pressure osmometry (VPO) data were all consistent with the structure of 3. N,N,N′,N′-tetramethylterephthalamide G was used as a guest for the binding study, and ESI-mass spectrum clearly displayed a characteristic, intense peak at m/z 1542 (41%), attributed to the fragment [3•G 3-3CF3SO3]3+ of 1:3 (host/guest) complex. The 1H NMR titration experiments gave association constants of 2300 ± 300 and 1200 ± 200 M-1 in CDCl3 at 25°C for two identical outer cavities, with weak positive cooperativity (Hill coefficient h = 1.3).",

author = "Jang, {Hye Young} and Chang, {Sung Youn} and Chang, {Kyoung Jin} and Jeong, {Kyu Sung}",

note = "Funding Information: This work was financially supported by the Korea Institute of the Center for Bioactive Molecular Hybrids (CBMH) and Science & Technology Evaluation and Planning (M10213030001- 02B1503-00310). ",

year = "2005",

month = apr,

day = "4",

doi = "10.1016/j.tetlet.2005.02.048",

language = "English",

volume = "46",

pages = "2433--2436",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "14",

}

TY - JOUR

T1 - Self-assembly and characterization of a giant metallocycle

AU - Jang, Hye Young

AU - Chang, Sung Youn

AU - Chang, Kyoung Jin

AU - Jeong, Kyu Sung

N1 - Funding Information: This work was financially supported by the Korea Institute of the Center for Bioactive Molecular Hybrids (CBMH) and Science & Technology Evaluation and Planning (M10213030001- 02B1503-00310).

PY - 2005/4/4

Y1 - 2005/4/4

N2 - A giant, 100-membered metallocycle 3 was prepared via coordination bond-based self-assembly from W-shaped ligand 9 and a palladium complex. Metallocycle 3 may create three topologically discrete subcavities, thus capable of binding up to three molecules of a diamide guest by hydrogen-bonding interactions. Elemental analysis, 1H NMR, and the ESI-mass spectra, and vapor pressure osmometry (VPO) data were all consistent with the structure of 3. N,N,N′,N′-tetramethylterephthalamide G was used as a guest for the binding study, and ESI-mass spectrum clearly displayed a characteristic, intense peak at m/z 1542 (41%), attributed to the fragment [3•G 3-3CF3SO3]3+ of 1:3 (host/guest) complex. The 1H NMR titration experiments gave association constants of 2300 ± 300 and 1200 ± 200 M-1 in CDCl3 at 25°C for two identical outer cavities, with weak positive cooperativity (Hill coefficient h = 1.3).

AB - A giant, 100-membered metallocycle 3 was prepared via coordination bond-based self-assembly from W-shaped ligand 9 and a palladium complex. Metallocycle 3 may create three topologically discrete subcavities, thus capable of binding up to three molecules of a diamide guest by hydrogen-bonding interactions. Elemental analysis, 1H NMR, and the ESI-mass spectra, and vapor pressure osmometry (VPO) data were all consistent with the structure of 3. N,N,N′,N′-tetramethylterephthalamide G was used as a guest for the binding study, and ESI-mass spectrum clearly displayed a characteristic, intense peak at m/z 1542 (41%), attributed to the fragment [3•G 3-3CF3SO3]3+ of 1:3 (host/guest) complex. The 1H NMR titration experiments gave association constants of 2300 ± 300 and 1200 ± 200 M-1 in CDCl3 at 25°C for two identical outer cavities, with weak positive cooperativity (Hill coefficient h = 1.3).

UR - http://www.scopus.com/inward/record.url?scp=17744376162&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=17744376162&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2005.02.048

DO - 10.1016/j.tetlet.2005.02.048

M3 - Article

AN - SCOPUS:17744376162

SN - 0040-4039

VL - 46

SP - 2433

EP - 2436

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 14

ER -

Self-assembly and characterization of a giant metallocycle

Abstract

Bibliographical note

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this