Synthesis, Structure, and Properties of Core-modified Pentaphyrins Containing Six meso Carbons

Emandi Ganapathi, Tamal Chatterjee, Way Zen Lee, Mangalampalli Ravikanth

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Our successful synthesis of nonaromatic 24π core-modified pentaphyrins containing six meso carbons is reported. The pentaphyrins were prepared by [3+2] condensation of butane-2,3-diyl-bisthiophene-2,5-diyl-bis(p-methoxyphenylmethanol) with different meso-aryl tripyrromethanes under mild acid-catalyzed conditions. By using this method, we obtained two stable, core-modified pentaphyrins containing six meso carbons in acceptable yields. The pentaphyrins were characterized by HR-MS, 1D, 2D NMR, absorption and electrochemical techniques, and also by X-ray crystallography for one of the pentaphyrin macrocycles. The crystal structure revealed that the macrocycle is almost planar and one of the thiophene rings, which is positioned opposite to the ethene bridged meso-carbons, is inverted. Our studies revealed that the macrocycles in their protonated form have specific sensing ability for CH3COO- ions.

Original languageEnglish
Pages (from-to)638-645
Number of pages8
JournalAsian Journal of Organic Chemistry
Volume4
Issue number7
DOIs
Publication statusPublished - 2015 Jan 1

Fingerprint

Carbon
Thiophenes
X ray crystallography
Condensation
Crystal structure
Nuclear magnetic resonance
Ions
Acids
butane
ethylene

Keywords

  • Chemosensors
  • Heterocycles
  • Macrocycles
  • Pentaphyrins
  • Tripyrromethanes

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis, Structure, and Properties of Core-modified Pentaphyrins Containing Six meso Carbons. / Ganapathi, Emandi; Chatterjee, Tamal; Lee, Way Zen; Ravikanth, Mangalampalli.

In: Asian Journal of Organic Chemistry, Vol. 4, No. 7, 01.01.2015, p. 638-645.

Research output: Contribution to journalArticle

Ganapathi, Emandi ; Chatterjee, Tamal ; Lee, Way Zen ; Ravikanth, Mangalampalli. / Synthesis, Structure, and Properties of Core-modified Pentaphyrins Containing Six meso Carbons. In: Asian Journal of Organic Chemistry. 2015 ; Vol. 4, No. 7. pp. 638-645.
@article{cf6b35fa9f3246d58b1d354e6937b6c6,
title = "Synthesis, Structure, and Properties of Core-modified Pentaphyrins Containing Six meso Carbons",
abstract = "Our successful synthesis of nonaromatic 24π core-modified pentaphyrins containing six meso carbons is reported. The pentaphyrins were prepared by [3+2] condensation of butane-2,3-diyl-bisthiophene-2,5-diyl-bis(p-methoxyphenylmethanol) with different meso-aryl tripyrromethanes under mild acid-catalyzed conditions. By using this method, we obtained two stable, core-modified pentaphyrins containing six meso carbons in acceptable yields. The pentaphyrins were characterized by HR-MS, 1D, 2D NMR, absorption and electrochemical techniques, and also by X-ray crystallography for one of the pentaphyrin macrocycles. The crystal structure revealed that the macrocycle is almost planar and one of the thiophene rings, which is positioned opposite to the ethene bridged meso-carbons, is inverted. Our studies revealed that the macrocycles in their protonated form have specific sensing ability for CH3COO- ions.",
keywords = "Chemosensors, Heterocycles, Macrocycles, Pentaphyrins, Tripyrromethanes",
author = "Emandi Ganapathi and Tamal Chatterjee and Lee, {Way Zen} and Mangalampalli Ravikanth",
year = "2015",
month = "1",
day = "1",
doi = "10.1002/ajoc.201500072",
language = "English",
volume = "4",
pages = "638--645",
journal = "Asian Journal of Organic Chemistry",
issn = "2193-5807",
publisher = "Wiley - VCH Verlag GmbH & CO. KGaA",
number = "7",

}

TY - JOUR

T1 - Synthesis, Structure, and Properties of Core-modified Pentaphyrins Containing Six meso Carbons

AU - Ganapathi, Emandi

AU - Chatterjee, Tamal

AU - Lee, Way Zen

AU - Ravikanth, Mangalampalli

PY - 2015/1/1

Y1 - 2015/1/1

N2 - Our successful synthesis of nonaromatic 24π core-modified pentaphyrins containing six meso carbons is reported. The pentaphyrins were prepared by [3+2] condensation of butane-2,3-diyl-bisthiophene-2,5-diyl-bis(p-methoxyphenylmethanol) with different meso-aryl tripyrromethanes under mild acid-catalyzed conditions. By using this method, we obtained two stable, core-modified pentaphyrins containing six meso carbons in acceptable yields. The pentaphyrins were characterized by HR-MS, 1D, 2D NMR, absorption and electrochemical techniques, and also by X-ray crystallography for one of the pentaphyrin macrocycles. The crystal structure revealed that the macrocycle is almost planar and one of the thiophene rings, which is positioned opposite to the ethene bridged meso-carbons, is inverted. Our studies revealed that the macrocycles in their protonated form have specific sensing ability for CH3COO- ions.

AB - Our successful synthesis of nonaromatic 24π core-modified pentaphyrins containing six meso carbons is reported. The pentaphyrins were prepared by [3+2] condensation of butane-2,3-diyl-bisthiophene-2,5-diyl-bis(p-methoxyphenylmethanol) with different meso-aryl tripyrromethanes under mild acid-catalyzed conditions. By using this method, we obtained two stable, core-modified pentaphyrins containing six meso carbons in acceptable yields. The pentaphyrins were characterized by HR-MS, 1D, 2D NMR, absorption and electrochemical techniques, and also by X-ray crystallography for one of the pentaphyrin macrocycles. The crystal structure revealed that the macrocycle is almost planar and one of the thiophene rings, which is positioned opposite to the ethene bridged meso-carbons, is inverted. Our studies revealed that the macrocycles in their protonated form have specific sensing ability for CH3COO- ions.

KW - Chemosensors

KW - Heterocycles

KW - Macrocycles

KW - Pentaphyrins

KW - Tripyrromethanes

UR - http://www.scopus.com/inward/record.url?scp=84935683515&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84935683515&partnerID=8YFLogxK

U2 - 10.1002/ajoc.201500072

DO - 10.1002/ajoc.201500072

M3 - Article

VL - 4

SP - 638

EP - 645

JO - Asian Journal of Organic Chemistry

JF - Asian Journal of Organic Chemistry

SN - 2193-5807

IS - 7

ER -