Nanoscale borromeates

Kelly S. Chichak; Andrea J. Peters; Stuart J. Cantrill; J. Fraser Stoddart

doi:10.1021/jo050969b

Nanoscale borromeates

Kelly S. Chichak, Andrea J. Peters, Stuart J. Cantrill, J. Fraser Stoddart^*

^*Corresponding author for this work

Chemistry

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

55 Scopus citations

Abstract

In addition to a parent zinc(II) Borromean ring (BR) complex, the preparation and characterization of two hexasubstituted BR complexes with either 4-acetoxymethylphenyl or 4-methylthiophenyl substituents associated in turn with all six pyridyl rings has been achieved convergently in good yields by appealing to the dynamic features of the reactions between primary amino groups in a preformed acyclic ligand and 2,6-diformylpyridine. Two molecules of the acyclic ligands react with two molecules of 2,6-diformylpyridine to form a cyclic [2 + 2] tetraimine in the presence of Zn(II) ions as templates in 2-propanol at 70 °C. The successful preparation of the two derivatives by convergent template-directed syntheses opens up opportunities to self-assemble, under equilibrium control, numerous nanoscale metallo-organic particles with potentially useful properties.

Original language	English (US)
Pages (from-to)	7956-7962
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	70
Issue number	20
DOIs	https://doi.org/10.1021/jo050969b
State	Published - Sep 20 2005

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1021/jo050969b

Cite this

@article{773cb3ebd5c14605a8aec5299355972b,

title = "Nanoscale borromeates",

abstract = "In addition to a parent zinc(II) Borromean ring (BR) complex, the preparation and characterization of two hexasubstituted BR complexes with either 4-acetoxymethylphenyl or 4-methylthiophenyl substituents associated in turn with all six pyridyl rings has been achieved convergently in good yields by appealing to the dynamic features of the reactions between primary amino groups in a preformed acyclic ligand and 2,6-diformylpyridine. Two molecules of the acyclic ligands react with two molecules of 2,6-diformylpyridine to form a cyclic [2 + 2] tetraimine in the presence of Zn(II) ions as templates in 2-propanol at 70 °C. The successful preparation of the two derivatives by convergent template-directed syntheses opens up opportunities to self-assemble, under equilibrium control, numerous nanoscale metallo-organic particles with potentially useful properties.",

author = "Chichak, {Kelly S.} and Peters, {Andrea J.} and Cantrill, {Stuart J.} and Stoddart, {J. Fraser}",

year = "2005",

month = sep,

day = "20",

doi = "10.1021/jo050969b",

language = "English (US)",

volume = "70",

pages = "7956--7962",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "20",

}

TY - JOUR

T1 - Nanoscale borromeates

AU - Chichak, Kelly S.

AU - Peters, Andrea J.

AU - Cantrill, Stuart J.

AU - Stoddart, J. Fraser

PY - 2005/9/20

Y1 - 2005/9/20

N2 - In addition to a parent zinc(II) Borromean ring (BR) complex, the preparation and characterization of two hexasubstituted BR complexes with either 4-acetoxymethylphenyl or 4-methylthiophenyl substituents associated in turn with all six pyridyl rings has been achieved convergently in good yields by appealing to the dynamic features of the reactions between primary amino groups in a preformed acyclic ligand and 2,6-diformylpyridine. Two molecules of the acyclic ligands react with two molecules of 2,6-diformylpyridine to form a cyclic [2 + 2] tetraimine in the presence of Zn(II) ions as templates in 2-propanol at 70 °C. The successful preparation of the two derivatives by convergent template-directed syntheses opens up opportunities to self-assemble, under equilibrium control, numerous nanoscale metallo-organic particles with potentially useful properties.

AB - In addition to a parent zinc(II) Borromean ring (BR) complex, the preparation and characterization of two hexasubstituted BR complexes with either 4-acetoxymethylphenyl or 4-methylthiophenyl substituents associated in turn with all six pyridyl rings has been achieved convergently in good yields by appealing to the dynamic features of the reactions between primary amino groups in a preformed acyclic ligand and 2,6-diformylpyridine. Two molecules of the acyclic ligands react with two molecules of 2,6-diformylpyridine to form a cyclic [2 + 2] tetraimine in the presence of Zn(II) ions as templates in 2-propanol at 70 °C. The successful preparation of the two derivatives by convergent template-directed syntheses opens up opportunities to self-assemble, under equilibrium control, numerous nanoscale metallo-organic particles with potentially useful properties.

UR - http://www.scopus.com/inward/record.url?scp=25444487281&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=25444487281&partnerID=8YFLogxK

U2 - 10.1021/jo050969b

DO - 10.1021/jo050969b

M3 - Article

C2 - 16277315

AN - SCOPUS:25444487281

SN - 0022-3263

VL - 70

SP - 7956

EP - 7962

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 20

ER -

Nanoscale borromeates

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this