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 language | English |
|---|---|
| Pages (from-to) | 638-645 |
| Number of pages | 8 |
| Journal | Asian Journal of Organic Chemistry |
| Volume | 4 |
| Issue number | 7 |
| DOIs | |
| Publication status | Published - 2015 Jan 1 |
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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 journal › Article
}
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
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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 -