Push–pull quinoidal porphyrins
Literature Information
Publication Date
2018-04-24
DOI
10.1039/C8OB00491A
Impact Factor
3.876
Authors
Martin J. Smith, Iain M. Blake, William Clegg, Harry L. Anderson
View Original
Abstract
A family of push–pull quinoidal porphyrin monomers has been prepared from a meso-formyl porphyrin by bromination, thioacetal formation, palladium-catalyzed coupling with malononitrile and oxidation with DDQ. Attempts at extending this synthesis to a push–pull quinoidal/cumulenic porphyrin dimer were not successful. The crystal structures of the quinoidal porphyrins indicate that there is no significant contribution from singlet biradical or zwitterionic resonance forms. The crystal structure of an ethyne-linked porphyrin dimer shows that the torsion angle between the porphyrin units is only about 3°, in keeping with crystallographic results on related compounds, but contrasting with the torsion angle of about 35° predicted by computational studies. The free-base quinoidal porphyrin monomers form tightly π-stacked layer structures, despite their curved geometries and bulky aryl substituents.
Related Literature
Government of Madras. Annual Report of the Government Analyst to September 30th, 1939
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Queensland. Report of the Government Analyst for the year ending June, 1932
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DOI: 10.1039/AN933580098A
Ministry of Health. The Public Health (preservatives, etc., in food) Amendment Regulations, 1940
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DOI: 10.1039/AN940650359A
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Source Journal
Organic & Biomolecular Chemistry
CiteScore:
3.4
Self-citation Rate:
10.3%
Articles per Year:
1041
Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.
Recommended Compounds
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Ethyl 5-[({[(2-methyl-2-propanyl)oxy]carbonyl}amino)methyl]-1,2-oxazole-3-carboxylate
CAS Number:
253196-37-1
Molecular Formula:
C12H18N2O5
![5,10-Dihydro-11H-dibenzo[b,e][1,4]diazepin-11-one structure](https://static.chemtradehub.com/structs/581/5814-41-5-0b01.webp "5,10-Dihydro-11H-dibenzo[b,e][1,4]diazepin-11-one structure")
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