Synthesis and Characterization of a New 26π-Aromatic Thiophene-Containing Macrocyclic Ligand

Martin R. Johnson; Douglas C. Miller; Kristine Bush; John J. Becker; James A. Ibers

doi:10.1021/jo00042a019

Synthesis and Characterization of a New 26π-Aromatic Thiophene-Containing Macrocyclic Ligand

Martin R. Johnson, Douglas C. Miller, Kristine Bush, John J. Becker, James A. Ibers

Chemistry

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

67 Scopus citations

Abstract

A new porphyrin-like or “pentaplanar” macrocyclic ligand (9) has been synthesized by a McMurray coupling of 2,5-bis(5-formyl-4-propyl-2-pyrrolyl)thiophene, followed by air oxidation in chloroform. This highly stable macrocycle is aromatic, as evidenced by its UV-visible and ¹H NMR spectra. The pathway to 9 as well as the synthesis of two asymmetric dipyrrolylthiophenes is also described.

Original language	English (US)
Pages (from-to)	4414-4417
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	57
Issue number	16
DOIs	https://doi.org/10.1021/jo00042a019
State	Published - Jul 1 1992

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1021/jo00042a019

Cite this

@article{5ce6bd8154f14bdb9a890da20804fd8f,

title = "Synthesis and Characterization of a New 26π-Aromatic Thiophene-Containing Macrocyclic Ligand",

abstract = "A new porphyrin-like or “pentaplanar” macrocyclic ligand (9) has been synthesized by a McMurray coupling of 2,5-bis(5-formyl-4-propyl-2-pyrrolyl)thiophene, followed by air oxidation in chloroform. This highly stable macrocycle is aromatic, as evidenced by its UV-visible and 1H NMR spectra. The pathway to 9 as well as the synthesis of two asymmetric dipyrrolylthiophenes is also described.",

author = "Johnson, {Martin R.} and Miller, {Douglas C.} and Kristine Bush and Becker, {John J.} and Ibers, {James A.}",

year = "1992",

month = jul,

day = "1",

doi = "10.1021/jo00042a019",

language = "English (US)",

volume = "57",

pages = "4414--4417",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "16",

}

TY - JOUR

T1 - Synthesis and Characterization of a New 26π-Aromatic Thiophene-Containing Macrocyclic Ligand

AU - Johnson, Martin R.

AU - Miller, Douglas C.

AU - Bush, Kristine

AU - Becker, John J.

AU - Ibers, James A.

PY - 1992/7/1

Y1 - 1992/7/1

N2 - A new porphyrin-like or “pentaplanar” macrocyclic ligand (9) has been synthesized by a McMurray coupling of 2,5-bis(5-formyl-4-propyl-2-pyrrolyl)thiophene, followed by air oxidation in chloroform. This highly stable macrocycle is aromatic, as evidenced by its UV-visible and 1H NMR spectra. The pathway to 9 as well as the synthesis of two asymmetric dipyrrolylthiophenes is also described.

AB - A new porphyrin-like or “pentaplanar” macrocyclic ligand (9) has been synthesized by a McMurray coupling of 2,5-bis(5-formyl-4-propyl-2-pyrrolyl)thiophene, followed by air oxidation in chloroform. This highly stable macrocycle is aromatic, as evidenced by its UV-visible and 1H NMR spectra. The pathway to 9 as well as the synthesis of two asymmetric dipyrrolylthiophenes is also described.

UR - http://www.scopus.com/inward/record.url?scp=0000205943&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0000205943&partnerID=8YFLogxK

U2 - 10.1021/jo00042a019

DO - 10.1021/jo00042a019

M3 - Article

AN - SCOPUS:0000205943

SN - 0022-3263

VL - 57

SP - 4414

EP - 4417

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 16

ER -

Synthesis and Characterization of a New 26π-Aromatic Thiophene-Containing Macrocyclic Ligand

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this